Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline United Airlines

The cheapest airline(s) flying from Washington to Chicago is United Airlines.

  • United Airlines United Airlines
  • Frontier Airlines Frontier Airlines
  • American Airlines American Airlines
  • JetBlue Airways JetBlue Airways
  • Alaska Airlines Alaska Airlines
Cheapest Month February

Travel Period: February 2025 - January 2026

The cheapest month(s) to fly from Washington to Chicago is February.

  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
Cheapest Day of the Week Friday

The cheapest day(s) of the week to fly from Washington to Chicago is Friday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Thu, 2 Jan, 2025

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    • Airline Filter by Airline
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      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 19:00 DCA
        20:25 ORD
        2Hrs, 25m Direct
      • DCAWashington Ronald Reagan National Airport 19:00 - ORD 20:25 2h 25m Direct
      • DCAWashington Ronald Reagan National Airport 19:00
      • ORDChicago O'Hare International Airport 20:25
      • 2h 25m
      • Direct
      • United Airlines (UA 3488)Embraer 175
      • United Airlines (UA 3488)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
      • Embraer 175
      • 19:10 BWI
        22:00 MDW
        3Hrs, 50m Direct
      • BWIBaltimore Washington International Airport 19:10 - MDW 22:00 3h 50m Direct
      • BWIBaltimore Washington International Airport 19:10
      • MDWChicago Midway Airport 22:00
      • 3h 50m
      • Direct
      • Southwest Airlines (WN 4418)Boeing 737 700
      • Southwest Airlines (WN 4418)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 19:30 BWI
        20:35 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 19:30 - MDW 20:35 2h 05m Direct
      • BWIBaltimore Washington International Airport 19:30
      • MDWChicago Midway Airport 20:35
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 854)Boeing 737 700
      • Southwest Airlines (WN 854)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 19:40 DCA
        20:45 MDW
        2Hrs, 05m Direct
      • DCAWashington Ronald Reagan National Airport 19:40 - MDW 20:45 2h 05m Direct
      • DCAWashington Ronald Reagan National Airport 19:40
      • MDWChicago Midway Airport 20:45
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 747)Boeing 737 800
      • Southwest Airlines (WN 747)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 20:10 BWI
        21:30 ORD
        2Hrs, 20m Direct
      • BWIBaltimore Washington International Airport 20:10 - ORD 21:30 2h 20m Direct
      • BWIBaltimore Washington International Airport 20:10
      • ORDChicago O'Hare International Airport 21:30
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 1849)Boeing 737 700
      • Southwest Airlines (WN 1849)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 20:10 BWI
        21:15 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 20:10 - MDW 21:15 2h 05m Direct
      • BWIBaltimore Washington International Airport 20:10
      • MDWChicago Midway Airport 21:15
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 4710)Boeing 737 800
      • Southwest Airlines (WN 4710)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 20:45 DCA
        22:05 ORD
        2Hrs, 20m Direct
      • DCAWashington Ronald Reagan National Airport 20:45 - ORD 22:05 2h 20m Direct
      • DCAWashington Ronald Reagan National Airport 20:45
      • ORDChicago O'Hare International Airport 22:05
      • 2h 20m
      • Direct
      • American Airlines (AA 1630)Boeing 737 800
      • American Airlines (AA 1630)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 21:15 DCA
        22:15 MDW
        2Hrs, 00m Direct
      • DCAWashington Ronald Reagan National Airport 21:15 - MDW 22:15 2h Direct
      • DCAWashington Ronald Reagan National Airport 21:15
      • MDWChicago Midway Airport 22:15
      • 2h
      • Direct
      • Southwest Airlines (WN 2080)Boeing 737 800
      • Southwest Airlines (WN 2080)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 22:05 BWI
        23:10 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 22:05 - MDW 23:10 2h 05m Direct
      • BWIBaltimore Washington International Airport 22:05
      • MDWChicago Midway Airport 23:10
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 724)Boeing 737 700
      • Southwest Airlines (WN 724)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 22:20 IAD
        23:25 ORD
        2Hrs, 05m Direct
      • IADWashington Dulles International Airport 22:20 - ORD 23:25 2h 05m Direct
      • IADWashington Dulles International Airport 22:20
      • ORDChicago O'Hare International Airport 23:25
      • 2h 05m
      • Direct
      • United Airlines (UA 1738)Boeing 757 200 Series
      • United Airlines (UA 1738)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 757 200 Series
      • 05:59 DCA
        07:19 ORD
        2Hrs, 20m Direct
      • DCAWashington Ronald Reagan National Airport 05:59 - ORD 07:19 2h 20m Direct
      • DCAWashington Ronald Reagan National Airport 05:59
      • ORDChicago O'Hare International Airport 07:19
      • 2h 20m
      • Direct
      • American Airlines (AA 2903)Boeing 737 800
      • American Airlines (AA 2903)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 06:00 DCA
        07:05 MDW
        2Hrs, 05m Direct
      • DCAWashington Ronald Reagan National Airport 06:00 - MDW 07:05 2h 05m Direct
      • DCAWashington Ronald Reagan National Airport 06:00
      • MDWChicago Midway Airport 07:05
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 940)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 940)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 06:20 BWI
        07:39 ORD
        2Hrs, 19m Direct
      • BWIBaltimore Washington International Airport 06:20 - ORD 07:39 2h 19m Direct
      • BWIBaltimore Washington International Airport 06:20
      • ORDChicago O'Hare International Airport 07:39
      • 2h 19m
      • Direct
      • United Airlines (UA 461)Boeing 737 Max 9 Passenger
      • United Airlines (UA 461)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 9 Passenger
      • 06:30 DCA
        07:48 ORD
        2Hrs, 18m Direct
      • DCAWashington Ronald Reagan National Airport 06:30 - ORD 07:48 2h 18m Direct
      • DCAWashington Ronald Reagan National Airport 06:30
      • ORDChicago O'Hare International Airport 07:48
      • 2h 18m
      • Direct
      • United Airlines (UA 1793)Boeing 737 800
      • United Airlines (UA 1793)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 06:35 BWI
        07:50 MDW
        2Hrs, 15m Direct
      • BWIBaltimore Washington International Airport 06:35 - MDW 07:50 2h 15m Direct
      • BWIBaltimore Washington International Airport 06:35
      • MDWChicago Midway Airport 07:50
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 594)Boeing 737 700
      • Southwest Airlines (WN 594)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 06:55 DCA
        08:05 MDW
        2Hrs, 10m Direct
      • DCAWashington Ronald Reagan National Airport 06:55 - MDW 08:05 2h 10m Direct
      • DCAWashington Ronald Reagan National Airport 06:55
      • MDWChicago Midway Airport 08:05
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 940)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 940)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 07:00 DCA
        08:27 ORD
        2Hrs, 27m Direct
      • DCAWashington Ronald Reagan National Airport 07:00 - ORD 08:27 2h 27m Direct
      • DCAWashington Ronald Reagan National Airport 07:00
      • ORDChicago O'Hare International Airport 08:27
      • 2h 27m
      • Direct
      • American Airlines (AA 2033)Boeing 737 800
      • American Airlines (AA 2033)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 07:04 DCA
        08:25 ORD
        2Hrs, 21m Direct
      • DCAWashington Ronald Reagan National Airport 07:04 - ORD 08:25 2h 21m Direct
      • DCAWashington Ronald Reagan National Airport 07:04
      • ORDChicago O'Hare International Airport 08:25
      • 2h 21m
      • Direct
      • American Airlines (AA 2033)Boeing 737 Max 8 Passenger
      • American Airlines (AA 2033)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 07:10 BWI
        08:20 MDW
        2Hrs, 10m Direct
      • BWIBaltimore Washington International Airport 07:10 - MDW 08:20 2h 10m Direct
      • BWIBaltimore Washington International Airport 07:10
      • MDWChicago Midway Airport 08:20
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 2833)Boeing 737 800
      • Southwest Airlines (WN 2833)
        • M
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 07:25 BWI
        08:30 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 07:25 - MDW 08:30 2h 05m Direct
      • BWIBaltimore Washington International Airport 07:25
      • MDWChicago Midway Airport 08:30
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 1204)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1204)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 07:30 DCA
        08:48 ORD
        2Hrs, 18m Direct
      • DCAWashington Ronald Reagan National Airport 07:30 - ORD 08:48 2h 18m Direct
      • DCAWashington Ronald Reagan National Airport 07:30
      • ORDChicago O'Hare International Airport 08:48
      • 2h 18m
      • Direct
      • United Airlines (UA 1540)Airbus
      • United Airlines (UA 1540)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • Airbus
      • 07:55 BWI
        09:00 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 07:55 - MDW 09:00 2h 05m Direct
      • BWIBaltimore Washington International Airport 07:55
      • MDWChicago Midway Airport 09:00
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 1204)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1204)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:30 DCA
        09:48 ORD
        2Hrs, 18m Direct
      • DCAWashington Ronald Reagan National Airport 08:30 - ORD 09:48 2h 18m Direct
      • DCAWashington Ronald Reagan National Airport 08:30
      • ORDChicago O'Hare International Airport 09:48
      • 2h 18m
      • Direct
      • United Airlines (UA 1316)Airbus
      • United Airlines (UA 1316)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus
      • 08:30 DCA
        09:48 ORD
        2Hrs, 18m Direct
      • DCAWashington Ronald Reagan National Airport 08:30 - ORD 09:48 2h 18m Direct
      • DCAWashington Ronald Reagan National Airport 08:30
      • ORDChicago O'Hare International Airport 09:48
      • 2h 18m
      • Direct
      • United Airlines (UA 1316)Airbus
      • United Airlines (UA 1316)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • Airbus
      • 08:35 IAD
        09:55 ORD
        2Hrs, 20m Direct
      • IADWashington Dulles International Airport 08:35 - ORD 09:55 2h 20m Direct
      • IADWashington Dulles International Airport 08:35
      • ORDChicago O'Hare International Airport 09:55
      • 2h 20m
      • Direct
      • United Airlines (UA 1710)Airbus
      • United Airlines (UA 1710)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus
      • 09:25 DCA
        10:30 MDW
        2Hrs, 05m Direct
      • DCAWashington Ronald Reagan National Airport 09:25 - MDW 10:30 2h 05m Direct
      • DCAWashington Ronald Reagan National Airport 09:25
      • MDWChicago Midway Airport 10:30
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 574)Boeing 737 700
      • Southwest Airlines (WN 574)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 10:07 BWI
        11:11 MDW
        2Hrs, 04m Direct
      • BWIBaltimore Washington International Airport 10:07 - MDW 11:11 2h 04m Direct
      • BWIBaltimore Washington International Airport 10:07
      • MDWChicago Midway Airport 11:11
      • 2h 04m
      • Direct
      • Frontier Airlines (F9 3087)Airbus A320 Neo
      • Frontier Airlines (F9 3087)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus A320 Neo
      • 10:30 DCA
        11:58 ORD
        2Hrs, 28m Direct
      • DCAWashington Ronald Reagan National Airport 10:30 - ORD 11:58 2h 28m Direct
      • DCAWashington Ronald Reagan National Airport 10:30
      • ORDChicago O'Hare International Airport 11:58
      • 2h 28m
      • Direct
      • United Airlines (UA 3544)Embraer 175
      • United Airlines (UA 3544)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Embraer 175
      • 10:59 BWI
        12:03 MDW
        2Hrs, 04m Direct
      • BWIBaltimore Washington International Airport 10:59 - MDW 12:03 2h 04m Direct
      • BWIBaltimore Washington International Airport 10:59
      • MDWChicago Midway Airport 12:03
      • 2h 04m
      • Direct
      • Frontier Airlines (F9 3087)Airbus A320 Neo
      • Frontier Airlines (F9 3087)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • Airbus A320 Neo
      • 11:30 DCA
        12:48 ORD
        2Hrs, 18m Direct
      • DCAWashington Ronald Reagan National Airport 11:30 - ORD 12:48 2h 18m Direct
      • DCAWashington Ronald Reagan National Airport 11:30
      • ORDChicago O'Hare International Airport 12:48
      • 2h 18m
      • Direct
      • United Airlines (UA 587)Airbus
      • United Airlines (UA 587)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Airbus
      • 11:30 BWI
        14:10 MDW
        3Hrs, 40m Direct
      • BWIBaltimore Washington International Airport 11:30 - MDW 14:10 3h 40m Direct
      • BWIBaltimore Washington International Airport 11:30
      • MDWChicago Midway Airport 14:10
      • 3h 40m
      • Direct
      • Southwest Airlines (WN 954)Boeing 737 700
      • Southwest Airlines (WN 954)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 11:45 DCA
        12:50 MDW
        2Hrs, 05m Direct
      • DCAWashington Ronald Reagan National Airport 11:45 - MDW 12:50 2h 05m Direct
      • DCAWashington Ronald Reagan National Airport 11:45
      • MDWChicago Midway Airport 12:50
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 3094)Boeing 737 700
      • Southwest Airlines (WN 3094)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 11:50 BWI
        14:05 MDW
        3Hrs, 15m Direct
      • BWIBaltimore Washington International Airport 11:50 - MDW 14:05 3h 15m Direct
      • BWIBaltimore Washington International Airport 11:50
      • MDWChicago Midway Airport 14:05
      • 3h 15m
      • Direct
      • Southwest Airlines (WN 2268)Boeing 737 700
      • Southwest Airlines (WN 2268)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 12:02 BWI
        13:06 MDW
        2Hrs, 04m Direct
      • BWIBaltimore Washington International Airport 12:02 - MDW 13:06 2h 04m Direct
      • BWIBaltimore Washington International Airport 12:02
      • MDWChicago Midway Airport 13:06
      • 2h 04m
      • Direct
      • Frontier Airlines (F9 3087)Airbus A320 Neo
      • Frontier Airlines (F9 3087)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus A320 Neo
      • 12:25 BWI
        13:30 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 12:25 - MDW 13:30 2h 05m Direct
      • BWIBaltimore Washington International Airport 12:25
      • MDWChicago Midway Airport 13:30
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 2833)Boeing 737 800
      • Southwest Airlines (WN 2833)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 12:40 DCA
        13:45 MDW
        2Hrs, 05m Direct
      • DCAWashington Ronald Reagan National Airport 12:40 - MDW 13:45 2h 05m Direct
      • DCAWashington Ronald Reagan National Airport 12:40
      • MDWChicago Midway Airport 13:45
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 2578)Boeing 737 700
      • Southwest Airlines (WN 2578)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 12:40 BWI
        14:00 ORD
        2Hrs, 20m Direct
      • BWIBaltimore Washington International Airport 12:40 - ORD 14:00 2h 20m Direct
      • BWIBaltimore Washington International Airport 12:40
      • ORDChicago O'Hare International Airport 14:00
      • 2h 20m
      • Direct
      • Southwest Airlines (WN 138)Boeing 737 800
      • Southwest Airlines (WN 138)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 13:10 BWI
        14:15 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 13:10 - MDW 14:15 2h 05m Direct
      • BWIBaltimore Washington International Airport 13:10
      • MDWChicago Midway Airport 14:15
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 2833)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2833)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 14:30 BWI
        17:05 MDW
        3Hrs, 35m Direct
      • BWIBaltimore Washington International Airport 14:30 - MDW 17:05 3h 35m Direct
      • BWIBaltimore Washington International Airport 14:30
      • MDWChicago Midway Airport 17:05
      • 3h 35m
      • Direct
      • Southwest Airlines (WN 2756)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2756)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 15:05 DCA
        16:15 MDW
        2Hrs, 10m Direct
      • DCAWashington Ronald Reagan National Airport 15:05 - MDW 16:15 2h 10m Direct
      • DCAWashington Ronald Reagan National Airport 15:05
      • MDWChicago Midway Airport 16:15
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 1542)Boeing 737 700
      • Southwest Airlines (WN 1542)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 15:35 BWI
        16:40 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 15:35 - MDW 16:40 2h 05m Direct
      • BWIBaltimore Washington International Airport 15:35
      • MDWChicago Midway Airport 16:40
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 4710)Boeing 737 800
      • Southwest Airlines (WN 4710)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 16:30 BWI
        19:50 MDW
        4Hrs, 20m Direct
      • BWIBaltimore Washington International Airport 16:30 - MDW 19:50 4h 20m Direct
      • BWIBaltimore Washington International Airport 16:30
      • MDWChicago Midway Airport 19:50
      • 4h 20m
      • Direct
      • Southwest Airlines (WN 391)Boeing 737 800
      • Southwest Airlines (WN 391)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 16:50 BWI
        19:35 MDW
        3Hrs, 45m Direct
      • BWIBaltimore Washington International Airport 16:50 - MDW 19:35 3h 45m Direct
      • BWIBaltimore Washington International Airport 16:50
      • MDWChicago Midway Airport 19:35
      • 3h 45m
      • Direct
      • Southwest Airlines (WN 1700)Boeing 737 800
      • Southwest Airlines (WN 1700)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 17:00 DCA
        18:18 ORD
        2Hrs, 18m Direct
      • DCAWashington Ronald Reagan National Airport 17:00 - ORD 18:18 2h 18m Direct
      • DCAWashington Ronald Reagan National Airport 17:00
      • ORDChicago O'Hare International Airport 18:18
      • 2h 18m
      • Direct
      • United Airlines (UA 230)Airbus
      • United Airlines (UA 230)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus
      • 17:35 IAD
        18:55 ORD
        2Hrs, 20m Direct
      • IADWashington Dulles International Airport 17:35 - ORD 18:55 2h 20m Direct
      • IADWashington Dulles International Airport 17:35
      • ORDChicago O'Hare International Airport 18:55
      • 2h 20m
      • Direct
      • United Airlines (UA 2497)Airbus
      • United Airlines (UA 2497)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Airbus
      • 17:40 BWI
        18:45 MDW
        2Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 17:40 - MDW 18:45 2h 05m Direct
      • BWIBaltimore Washington International Airport 17:40
      • MDWChicago Midway Airport 18:45
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 1291)Boeing 737 800
      • Southwest Airlines (WN 1291)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 17:55 BWI
        21:00 MDW
        4Hrs, 05m Direct
      • BWIBaltimore Washington International Airport 17:55 - MDW 21:00 4h 05m Direct
      • BWIBaltimore Washington International Airport 17:55
      • MDWChicago Midway Airport 21:00
      • 4h 05m
      • Direct
      • Southwest Airlines (WN 2562)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2562)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 18:00 DCA
        19:24 ORD
        2Hrs, 24m Direct
      • DCAWashington Ronald Reagan National Airport 18:00 - ORD 19:24 2h 24m Direct
      • DCAWashington Ronald Reagan National Airport 18:00
      • ORDChicago O'Hare International Airport 19:24
      • 2h 24m
      • Direct
      • United Airlines (UA 3488)Embraer 175
      • United Airlines (UA 3488)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Embraer 175
      • 18:00 DCA
        19:18 ORD
        2Hrs, 18m Direct
      • DCAWashington Ronald Reagan National Airport 18:00 - ORD 19:18 2h 18m Direct
      • DCAWashington Ronald Reagan National Airport 18:00
      • ORDChicago O'Hare International Airport 19:18
      • 2h 18m
      • Direct
      • United Airlines (UA 2148)Airbus
      • United Airlines (UA 2148)
        • M
        • -
        • W
        • -
        • -
        • S
        • S
      • Airbus
      • 18:15 BWI
        21:45 MDW
        4Hrs, 30m Direct
      • BWIBaltimore Washington International Airport 18:15 - MDW 21:45 4h 30m Direct
      • BWIBaltimore Washington International Airport 18:15
      • MDWChicago Midway Airport 21:45
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 2641)Boeing 737 800
      • Southwest Airlines (WN 2641)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 18:25 BWI
        21:35 MDW
        4Hrs, 10m Direct
      • BWIBaltimore Washington International Airport 18:25 - MDW 21:35 4h 10m Direct
      • BWIBaltimore Washington International Airport 18:25
      • MDWChicago Midway Airport 21:35
      • 4h 10m
      • Direct
      • Southwest Airlines (WN 3915)Boeing 737 700
      • Southwest Airlines (WN 3915)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 18:35 DCA
        19:40 MDW
        2Hrs, 05m Direct
      • DCAWashington Ronald Reagan National Airport 18:35 - MDW 19:40 2h 05m Direct
      • DCAWashington Ronald Reagan National Airport 18:35
      • MDWChicago Midway Airport 19:40
      • 2h 05m
      • Direct
      • Southwest Airlines (WN 1679)Boeing 737 700
      • Southwest Airlines (WN 1679)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 19:05 DCA
        22:20 MDW
        4Hrs, 15m 1 Stop (BNA)
      • DCAWashington Ronald Reagan National Airport 19:05 - MDW 22:20 4h 15m 1 Stop (BNA) Nashville
      • DCAWashington Ronald Reagan National Airport 19:05
        BNANashville Airport 20:45
      • BNANashville Airport 20:05
        MDWChicago Midway Airport 22:20
      • 4h 15m (40m)
      • 1 Stop BNA · Nashville 40m
      • Southwest Airlines (WN 1693)Boeing 737 700
        Southwest Airlines (WN 1647)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1693)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 19:30 BWI
        23:10 MDW
        4Hrs, 40m 1 Stop (ATL)
      • BWIBaltimore Washington International Airport 19:30 - MDW 23:10 4h 40m 1 Stop (ATL) Atlanta
      • BWIBaltimore Washington International Airport 19:30
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:30
        MDWChicago Midway Airport 23:10
      • 4h 40m (45m)
      • 1 Stop ATL · Atlanta 45m
      • Southwest Airlines (WN 250)Boeing 737 800
        Southwest Airlines (WN 4703)Boeing 737 800
      • Southwest Airlines (WN 250)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:35 DCA
        23:10 MDW
        4Hrs, 35m 1 Stop (ATL)
      • DCAWashington Ronald Reagan National Airport 19:35 - MDW 23:10 4h 35m 1 Stop (ATL) Atlanta
      • DCAWashington Ronald Reagan National Airport 19:35
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:35
        MDWChicago Midway Airport 23:10
      • 4h 35m (40m)
      • 1 Stop ATL · Atlanta 40m
      • Southwest Airlines (WN 4199)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4703)Boeing 737 800
      • Southwest Airlines (WN 4199)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 20:10 IAD
        23:37 ORD
        4Hrs, 27m 1 Stop (CLT)
      • IADWashington Dulles International Airport 20:10 - ORD 23:37 4h 27m 1 Stop (CLT) Charlotte
      • IADWashington Dulles International Airport 20:10
        CLTCharlotte Airport 22:25
      • CLTCharlotte Airport 21:50
        ORDChicago O'Hare International Airport 23:37
      • 4h 27m (35m)
      • 1 Stop CLT · Charlotte 35m
      • American Airlines (AA 5447)Crj 700 Canadair Regional
        American Airlines (AA 1180)Boeing 737 800
      • American Airlines (AA 5447)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 06:05 DCA
        10:35 MDW
        5Hrs, 30m 1 Stop (MCI)
      • DCAWashington Ronald Reagan National Airport 06:05 - MDW 10:35 5h 30m 1 Stop (MCI) Kansas City
      • DCAWashington Ronald Reagan National Airport 06:05
        MCIKansas City International Airport 09:10
      • MCIKansas City International Airport 07:55
        MDWChicago Midway Airport 10:35
      • 5h 30m (1h 15m)
      • 1 Stop MCI · Kansas City 1h 15m
      • Southwest Airlines (WN 416)Boeing 737 700
        Southwest Airlines (WN 2663)Boeing 737 700
      • Southwest Airlines (WN 416)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:05 DCA
        10:10 MDW
        5Hrs, 05m 1 Stop (ATL)
      • DCAWashington Ronald Reagan National Airport 06:05 - MDW 10:10 5h 05m 1 Stop (ATL) Atlanta
      • DCAWashington Ronald Reagan National Airport 06:05
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:05
        MDWChicago Midway Airport 10:10
      • 5h 05m (1h 10m)
      • 1 Stop ATL · Atlanta 1h 10m
      • Southwest Airlines (WN 565)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1925)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 565)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:05 DCA
        10:00 MDW
        4Hrs, 55m 1 Stop (ATL)
      • DCAWashington Ronald Reagan National Airport 06:05 - MDW 10:00 4h 55m 1 Stop (ATL) Atlanta
      • DCAWashington Ronald Reagan National Airport 06:05
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:05
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:05
        MDWChicago Midway Airport 10:00
      • 4h 55m (1h)
      • 1 Stop ATL · Atlanta 1h
      • Southwest Airlines (WN 565)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1432)Boeing 737 700
      • Southwest Airlines (WN 565)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:45 BWI
        11:01 ORD
        5Hrs, 16m 1 Stop (CLT)
      • BWIBaltimore Washington International Airport 06:45 - ORD 11:01 5h 16m 1 Stop (CLT) Charlotte
      • BWIBaltimore Washington International Airport 06:45
        CLTCharlotte Airport 09:40
      • CLTCharlotte Airport 08:35
        ORDChicago O'Hare International Airport 11:01
      • 5h 16m (1h 05m)
      • 1 Stop CLT · Charlotte 1h 05m
      • American Airlines (AA 2758)Boeing 737 800
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 2758)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:52 DCA
        11:08 ORD
        5Hrs, 16m 1 Stop (IND)
      • DCAWashington Ronald Reagan National Airport 06:52 - ORD 11:08 5h 16m 1 Stop (IND) Indianapolis
      • DCAWashington Ronald Reagan National Airport 06:52
        INDIndianapolis Airport 10:55
      • INDIndianapolis Airport 08:58
        ORDChicago O'Hare International Airport 11:08
      • 5h 16m (1h 57m)
      • 1 Stop IND · Indianapolis 1h 57m
      • American Airlines (AA 4340)Embraer Emb 175
        American Airlines (AA 3713)Embraer 170
      • American Airlines (AA 4340)
        • M
        • T
        • -
        • T
        • F
        • -
        • S
      • 07:30 BWI
        11:50 MDW
        5Hrs, 20m 1 Stop (STL)
      • BWIBaltimore Washington International Airport 07:30 - MDW 11:50 5h 20m 1 Stop (STL) Saint Louis
      • BWIBaltimore Washington International Airport 07:30
        STLSt Louis Lambert Intl Airport 10:40
      • STLSt Louis Lambert Intl Airport 08:55
        MDWChicago Midway Airport 11:50
      • 5h 20m (1h 45m)
      • 1 Stop STL · Saint Louis 1h 45m
      • Southwest Airlines (WN 1583)Boeing 737 700
        Southwest Airlines (WN 2364)Boeing 737 800
      • Southwest Airlines (WN 1583)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:40 BWI
        12:10 MDW
        5Hrs, 30m 1 Stop (BOS)
      • BWIBaltimore Washington International Airport 07:40 - MDW 12:10 5h 30m 1 Stop (BOS) Boston
      • BWIBaltimore Washington International Airport 07:40
        BOSBoston Logan International Airport 10:25
      • BOSBoston Logan International Airport 09:10
        MDWChicago Midway Airport 12:10
      • 5h 30m (1h 15m)
      • 1 Stop BOS · Boston 1h 15m
      • Southwest Airlines (WN 933)Boeing 737 800
        Southwest Airlines (WN 935)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 933)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:15 IAD
        12:05 ORD
        4Hrs, 50m 1 Stop (GSP)
      • IADWashington Dulles International Airport 08:15 - ORD 12:05 4h 50m 1 Stop (GSP) Greenville
      • IADWashington Dulles International Airport 08:15
        GSPGreenville/Spartanburg Airport 10:50
      • GSPGreenville/Spartanburg Airport 09:53
        ORDChicago O'Hare International Airport 12:05
      • 4h 50m (57m)
      • 1 Stop GSP · Greenville 57m
      • United Airlines (UA 4961)Embraer
        United Airlines (UA 4494)Canadair Regional Jet 550
      • United Airlines (UA 4961)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 08:20 IAD
        12:01 ORD
        4Hrs, 41m 1 Stop (CMH)
      • IADWashington Dulles International Airport 08:20 - ORD 12:01 4h 41m 1 Stop (CMH) Columbus
      • IADWashington Dulles International Airport 08:20
        CMHColumbus Port Columbus Intl Airport 11:25
      • CMHColumbus Port Columbus Intl Airport 09:47
        ORDChicago O'Hare International Airport 12:01
      • 4h 41m (1h 38m)
      • 1 Stop CMH · Columbus 1h 38m
      • United Airlines (UA 6048)Embraer 175
        United Airlines (UA 3442)Embraer 175
      • United Airlines (UA 6048)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:20 IAD
        12:55 ORD
        5Hrs, 35m 1 Stop (RDU)
      • IADWashington Dulles International Airport 08:20 - ORD 12:55 5h 35m 1 Stop (RDU) Morrisville
      • IADWashington Dulles International Airport 08:20
        RDURaleigh/Durham Airport 11:17
      • RDURaleigh/Durham Airport 09:39
        ORDChicago O'Hare International Airport 12:55
      • 5h 35m (1h 38m)
      • 1 Stop RDU · Morrisville 1h 38m
      • United Airlines (UA 4430)Canadair Regional Jet 550
        United Airlines (UA 3598)Embraer 175
      • United Airlines (UA 4430)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 08:21 IAD
        11:34 ORD
        4Hrs, 13m 1 Stop (CLE)
      • IADWashington Dulles International Airport 08:21 - ORD 11:34 4h 13m 1 Stop (CLE) Cleveland
      • IADWashington Dulles International Airport 08:21
        CLECleveland Hopkins International Airport 10:52
      • CLECleveland Hopkins International Airport 09:50
        ORDChicago O'Hare International Airport 11:34
      • 4h 13m (1h 02m)
      • 1 Stop CLE · Cleveland 1h 02m
      • United Airlines (UA 4578)Canadair Regional Jet 550
        United Airlines (UA 5333)Embraer 175
      • United Airlines (UA 4578)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:25 IAD
        11:49 ORD
        4Hrs, 24m 1 Stop (SYR)
      • IADWashington Dulles International Airport 08:25 - ORD 11:49 4h 24m 1 Stop (SYR) Syracuse
      • IADWashington Dulles International Airport 08:25
        SYRSyracuse Airport 10:25
      • SYRSyracuse Airport 09:49
        ORDChicago O'Hare International Airport 11:49
      • 4h 24m (36m)
      • 1 Stop SYR · Syracuse 36m
      • United Airlines (UA 4880)Embraer
        United Airlines (UA 4513)Canadair Regional Jet 550
      • United Airlines (UA 4880)
        • M
        • T
        • -
        • T
        • F
        • -
        • -
      • 08:25 IAD
        13:00 ORD
        5Hrs, 35m 1 Stop (BOS)
      • IADWashington Dulles International Airport 08:25 - ORD 13:00 5h 35m 1 Stop (BOS) Boston
      • IADWashington Dulles International Airport 08:25
        BOSBoston Logan International Airport 11:02
      • BOSBoston Logan International Airport 10:00
        ORDChicago O'Hare International Airport 13:00
      • 5h 35m (1h 02m)
      • 1 Stop BOS · Boston 1h 02m
      • United Airlines (UA 641)Boeing 737 800
        United Airlines (UA 267)Boeing 737 800
      • United Airlines (UA 641)
        • -
        • -
        • W
        • -
        • -
        • -
        • S
      • 08:25 IAD
        11:45 ORD
        4Hrs, 20m 1 Stop (PIT)
      • IADWashington Dulles International Airport 08:25 - ORD 11:45 4h 20m 1 Stop (PIT) Pittsburgh
      • IADWashington Dulles International Airport 08:25
        PITPittsburgh International Airport 10:50
      • PITPittsburgh International Airport 09:40
        ORDChicago O'Hare International Airport 11:45
      • 4h 20m (1h 10m)
      • 1 Stop PIT · Pittsburgh 1h 10m
      • United Airlines (UA 6090)Embraer 175
        United Airlines (UA 3686)Embraer 175
      • United Airlines (UA 6090)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 08:25 IAD
        11:55 ORD
        4Hrs, 30m 1 Stop (PIT)
      • IADWashington Dulles International Airport 08:25 - ORD 11:55 4h 30m 1 Stop (PIT) Pittsburgh
      • IADWashington Dulles International Airport 08:25
        PITPittsburgh International Airport 11:00
      • PITPittsburgh International Airport 09:40
        ORDChicago O'Hare International Airport 11:55
      • 4h 30m (1h 20m)
      • 1 Stop PIT · Pittsburgh 1h 20m
      • United Airlines (UA 6090)Embraer 175
        United Airlines (UA 3686)Embraer 175
      • United Airlines (UA 6090)
        • M
        • T
        • -
        • T
        • F
        • -
        • S
      • 08:25 IAD
        11:55 ORD
        4Hrs, 30m 1 Stop (PIT)
      • IADWashington Dulles International Airport 08:25 - ORD 11:55 4h 30m 1 Stop (PIT) Pittsburgh
      • IADWashington Dulles International Airport 08:25
        PITPittsburgh International Airport 11:00
      • PITPittsburgh International Airport 09:41
        ORDChicago O'Hare International Airport 11:55
      • 4h 30m (1h 19m)
      • 1 Stop PIT · Pittsburgh 1h 19m
      • United Airlines (UA 4291)Embraer
        United Airlines (UA 3686)Embraer 175
      • United Airlines (UA 4291)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:30 IAD
        12:05 ORD
        4Hrs, 35m 1 Stop (STL)
      • IADWashington Dulles International Airport 08:30 - ORD 12:05 4h 35m 1 Stop (STL) Saint Louis
      • IADWashington Dulles International Airport 08:30
        STLSt Louis Lambert Intl Airport 10:35
      • STLSt Louis Lambert Intl Airport 09:54
        ORDChicago O'Hare International Airport 12:05
      • 4h 35m (41m)
      • 1 Stop STL · Saint Louis 41m
      • United Airlines (UA 4427)Canadair Regional Jet 550
        United Airlines (UA 4426)Canadair Regional Jet 550
      • United Airlines (UA 4427)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:30 IAD
        12:05 ORD
        4Hrs, 35m 1 Stop (PHL)
      • IADWashington Dulles International Airport 08:30 - ORD 12:05 4h 35m 1 Stop (PHL) Philadelphia
      • IADWashington Dulles International Airport 08:30
        PHLPhiladelphia International Airport 10:33
      • PHLPhiladelphia International Airport 09:41
        ORDChicago O'Hare International Airport 12:05
      • 4h 35m (52m)
      • 1 Stop PHL · Philadelphia 52m
      • United Airlines (UA 4590)Canadair Regional Jet 550
        United Airlines (UA 337)Boeing 737 800
      • United Airlines (UA 4590)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 08:30 IAD
        12:59 ORD
        5Hrs, 29m 1 Stop (STL)
      • IADWashington Dulles International Airport 08:30 - ORD 12:59 5h 29m 1 Stop (STL) Saint Louis
      • IADWashington Dulles International Airport 08:30
        STLSt Louis Lambert Intl Airport 11:30
      • STLSt Louis Lambert Intl Airport 09:54
        ORDChicago O'Hare International Airport 12:59
      • 5h 29m (1h 36m)
      • 1 Stop STL · Saint Louis 1h 36m
      • United Airlines (UA 4427)Canadair Regional Jet 550
        United Airlines (UA 4383)Canadair Regional Jet 550
      • United Airlines (UA 4427)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:30 DCA
        12:45 ORD
        5Hrs, 15m 1 Stop (LGA)
      • DCAWashington Ronald Reagan National Airport 08:30 - ORD 12:45 5h 15m 1 Stop (LGA) New York City
      • DCAWashington Ronald Reagan National Airport 08:30
        LGANew York La Guardia Airport 11:00
      • LGANew York La Guardia Airport 09:56
        ORDChicago O'Hare International Airport 12:45
      • 5h 15m (1h 04m)
      • 1 Stop LGA · New York City 1h 04m
      • American Airlines (AA 4664)Embraer Emb 175
        American Airlines (AA 3205)Airbus
      • American Airlines (AA 4664)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 08:35 IAD
        11:54 ORD
        4Hrs, 19m 1 Stop (RIC)
      • IADWashington Dulles International Airport 08:35 - ORD 11:54 4h 19m 1 Stop (RIC) Richmond
      • IADWashington Dulles International Airport 08:35
        RICRichmond Airport 10:25
      • RICRichmond Airport 09:42
        ORDChicago O'Hare International Airport 11:54
      • 4h 19m (43m)
      • 1 Stop RIC · Richmond 43m
      • United Airlines (UA 4370)Embraer
        United Airlines (UA 4487)Canadair Regional Jet 550
      • United Airlines (UA 4370)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:35 IAD
        11:54 ORD
        4Hrs, 19m 1 Stop (SCE)
      • IADWashington Dulles International Airport 08:35 - ORD 11:54 4h 19m 1 Stop (SCE) State College
      • IADWashington Dulles International Airport 08:35
        SCEState College Airport 10:43
      • SCEState College Airport 09:40
        ORDChicago O'Hare International Airport 11:54
      • 4h 19m (1h 03m)
      • 1 Stop SCE · State College 1h 03m
      • United Airlines (UA 4319)Embraer
        United Airlines (UA 4471)Canadair Regional Jet 550
      • United Airlines (UA 4319)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 08:35 IAD
        12:00 ORD
        4Hrs, 25m 1 Stop (SCE)
      • IADWashington Dulles International Airport 08:35 - ORD 12:00 4h 25m 1 Stop (SCE) State College
      • IADWashington Dulles International Airport 08:35
        SCEState College Airport 10:43
      • SCEState College Airport 09:40
        ORDChicago O'Hare International Airport 12:00
      • 4h 25m (1h 03m)
      • 1 Stop SCE · State College 1h 03m
      • United Airlines (UA 4319)Embraer
        United Airlines (UA 5635)Crj Canadair Regional
      • United Airlines (UA 4319)
        • M
        • T
        • -
        • T
        • F
        • -
        • -
      • 08:40 IAD
        12:02 ORD
        4Hrs, 22m 1 Stop (ROA)
      • IADWashington Dulles International Airport 08:40 - ORD 12:02 4h 22m 1 Stop (ROA) Roanoke
      • IADWashington Dulles International Airport 08:40
        ROARoanoke Airport 10:52
      • ROARoanoke Airport 09:52
        ORDChicago O'Hare International Airport 12:02
      • 4h 22m (1h)
      • 1 Stop ROA · Roanoke 1h
      • United Airlines (UA 4368)Embraer
        United Airlines (UA 5457)Embraer 175
      • United Airlines (UA 4368)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 08:40 BWI
        12:40 MDW
        5Hrs, 00m 1 Stop (MCI)
      • BWIBaltimore Washington International Airport 08:40 - MDW 12:40 5h 1 Stop (MCI) Kansas City
      • BWIBaltimore Washington International Airport 08:40
        MCIKansas City International Airport 11:15
      • MCIKansas City International Airport 10:35
        MDWChicago Midway Airport 12:40
      • 5h (40m)
      • 1 Stop MCI · Kansas City 40m
      • Southwest Airlines (WN 1053)Boeing 737 700
        Southwest Airlines (WN 2847)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1053)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 08:40 IAD
        11:52 ORD
        4Hrs, 12m 1 Stop (IND)
      • IADWashington Dulles International Airport 08:40 - ORD 11:52 4h 12m 1 Stop (IND) Indianapolis
      • IADWashington Dulles International Airport 08:40
        INDIndianapolis Airport 11:27
      • INDIndianapolis Airport 10:35
        ORDChicago O'Hare International Airport 11:52
      • 4h 12m (52m)
      • 1 Stop IND · Indianapolis 52m
      • United Airlines (UA 3561)Embraer 175
        United Airlines (UA 3677)Embraer 175
      • United Airlines (UA 3561)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:40 IAD
        13:00 ORD
        5Hrs, 20m 1 Stop (ORF)
      • IADWashington Dulles International Airport 08:40 - ORD 13:00 5h 20m 1 Stop (ORF) Norfolk
      • IADWashington Dulles International Airport 08:40
        ORFNorfolk International Airport 11:20
      • ORFNorfolk International Airport 09:51
        ORDChicago O'Hare International Airport 13:00
      • 5h 20m (1h 29m)
      • 1 Stop ORF · Norfolk 1h 29m
      • United Airlines (UA 4944)Embraer
        United Airlines (UA 5525)Embraer 175
      • United Airlines (UA 4944)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:45 IAD
        13:07 ORD
        5Hrs, 22m 1 Stop (ALB)
      • IADWashington Dulles International Airport 08:45 - ORD 13:07 5h 22m 1 Stop (ALB) Albany
      • IADWashington Dulles International Airport 08:45
        ALBAlbany International Airport 11:15
      • ALBAlbany International Airport 10:15
        ORDChicago O'Hare International Airport 13:07
      • 5h 22m (1h)
      • 1 Stop ALB · Albany 1h
      • United Airlines (UA 4812)Embraer
        United Airlines (UA 5971)Embraer 175
      • United Airlines (UA 4812)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 08:52 IAD
        12:05 ORD
        4Hrs, 13m 1 Stop (CVG)
      • IADWashington Dulles International Airport 08:52 - ORD 12:05 4h 13m 1 Stop (CVG) Cincinnati
      • IADWashington Dulles International Airport 08:52
        CVGCincinnati Northern Kentucky Intl Airport 11:27
      • CVGCincinnati Northern Kentucky Intl Airport 10:39
        ORDChicago O'Hare International Airport 12:05
      • 4h 13m (48m)
      • 1 Stop CVG · Cincinnati 48m
      • United Airlines (UA 3548)Embraer 175
        United Airlines (UA 3485)Embraer 175
      • United Airlines (UA 3548)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:55 IAD
        13:07 ORD
        5Hrs, 12m 1 Stop (SAV)
      • IADWashington Dulles International Airport 08:55 - ORD 13:07 5h 12m 1 Stop (SAV) Savannah
      • IADWashington Dulles International Airport 08:55
        SAVSavannah/Hilton Head International Airport 11:30
      • SAVSavannah/Hilton Head International Airport 10:57
        ORDChicago O'Hare International Airport 13:07
      • 5h 12m (33m)
      • 1 Stop SAV · Savannah 33m
      • United Airlines (UA 4419)Canadair Regional Jet 550
        United Airlines (UA 3690)Embraer 175
      • United Airlines (UA 4419)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 09:00 IAD
        13:15 ORD
        5Hrs, 15m 1 Stop (MSP)
      • IADWashington Dulles International Airport 09:00 - ORD 13:15 5h 15m 1 Stop (MSP) Minneapolis
      • IADWashington Dulles International Airport 09:00
        MSPMinneapolis International Airport 11:33
      • MSPMinneapolis International Airport 10:52
        ORDChicago O'Hare International Airport 13:15
      • 5h 15m (41m)
      • 1 Stop MSP · Minneapolis 41m
      • United Airlines (UA 6067)Embraer 175
        United Airlines (UA 356)Boeing 737 800
      • United Airlines (UA 6067)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 09:00 IAD
        13:15 ORD
        5Hrs, 15m 1 Stop (BTV)
      • IADWashington Dulles International Airport 09:00 - ORD 13:15 5h 15m 1 Stop (BTV) Burlington
      • IADWashington Dulles International Airport 09:00
        BTVBurlington Airport 11:19
      • BTVBurlington Airport 10:37
        ORDChicago O'Hare International Airport 13:15
      • 5h 15m (42m)
      • 1 Stop BTV · Burlington 42m
      • United Airlines (UA 1016)Airbus
        United Airlines (UA 3429)Embraer 175
      • United Airlines (UA 1016)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 09:00 IAD
        13:15 ORD
        5Hrs, 15m 1 Stop (BTV)
      • IADWashington Dulles International Airport 09:00 - ORD 13:15 5h 15m 1 Stop (BTV) Burlington
      • IADWashington Dulles International Airport 09:00
        BTVBurlington Airport 11:19
      • BTVBurlington Airport 10:41
        ORDChicago O'Hare International Airport 13:15
      • 5h 15m (38m)
      • 1 Stop BTV · Burlington 38m
      • United Airlines (UA 6169)Embraer 175
        United Airlines (UA 3429)Embraer 175
      • United Airlines (UA 6169)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 09:00 IAD
        13:09 ORD
        5Hrs, 09m 1 Stop (MSP)
      • IADWashington Dulles International Airport 09:00 - ORD 13:09 5h 09m 1 Stop (MSP) Minneapolis
      • IADWashington Dulles International Airport 09:00
        MSPMinneapolis International Airport 11:23
      • MSPMinneapolis International Airport 10:52
        ORDChicago O'Hare International Airport 13:09
      • 5h 09m (31m)
      • 1 Stop MSP · Minneapolis 31m
      • United Airlines (UA 6067)Embraer 175
        United Airlines (UA 3572)Embraer 175
      • United Airlines (UA 6067)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 09:00 IAD
        13:19 ORD
        5Hrs, 19m 1 Stop (MSP)
      • IADWashington Dulles International Airport 09:00 - ORD 13:19 5h 19m 1 Stop (MSP) Minneapolis
      • IADWashington Dulles International Airport 09:00
        MSPMinneapolis International Airport 11:33
      • MSPMinneapolis International Airport 10:52
        ORDChicago O'Hare International Airport 13:19
      • 5h 19m (41m)
      • 1 Stop MSP · Minneapolis 41m
      • United Airlines (UA 6067)Embraer 175
        United Airlines (UA 3572)Embraer 175
      • United Airlines (UA 6067)
        • -
        • -
        • W
        • -
        • -
        • S
        • -
      • 09:20 BWI
        13:00 ORD
        4Hrs, 40m 1 Stop (BNA)
      • BWIBaltimore Washington International Airport 09:20 - ORD 13:00 4h 40m 1 Stop (BNA) Nashville
      • BWIBaltimore Washington International Airport 09:20
        BNANashville Airport 11:15
      • BNANashville Airport 10:25
        ORDChicago O'Hare International Airport 13:00
      • 4h 40m (50m)
      • 1 Stop BNA · Nashville 50m
      • Southwest Airlines (WN 1227)Boeing 737 700
        Southwest Airlines (WN 983)Boeing 737 800
      • Southwest Airlines (WN 1227)
        • -
        • T
        • W
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        • -
        • -
        • -
      • 09:40 BWI
        14:00 MDW
        5Hrs, 20m 1 Stop (BNA)
      • BWIBaltimore Washington International Airport 09:40 - MDW 14:00 5h 20m 1 Stop (BNA) Nashville
      • BWIBaltimore Washington International Airport 09:40
        BNANashville Airport 12:25
      • BNANashville Airport 10:45
        MDWChicago Midway Airport 14:00
      • 5h 20m (1h 40m)
      • 1 Stop BNA · Nashville 1h 40m
      • Southwest Airlines (WN 3123)Boeing 737 800
        Southwest Airlines (WN 2412)Boeing 737 700
      • Southwest Airlines (WN 3123)
        • -
        • -
        • -
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        • S
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      • 09:55 BWI
        14:15 MDW
        5Hrs, 20m 1 Stop (CMH)
      • BWIBaltimore Washington International Airport 09:55 - MDW 14:15 5h 20m 1 Stop (CMH) Columbus
      • BWIBaltimore Washington International Airport 09:55
        CMHColumbus Port Columbus Intl Airport 14:00
      • CMHColumbus Port Columbus Intl Airport 11:20
        MDWChicago Midway Airport 14:15
      • 5h 20m (2h 40m)
      • 1 Stop CMH · Columbus 2h 40m
      • Southwest Airlines (WN 250)Boeing 737 700
        Southwest Airlines (WN 2328)Boeing 737 700
      • Southwest Airlines (WN 250)
        • -
        • T
        • W
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        • -
      • 09:59 DCA
        13:55 ORD
        4Hrs, 56m 1 Stop (BDL)
      • DCAWashington Ronald Reagan National Airport 09:59 - ORD 13:55 4h 56m 1 Stop (BDL) Hartford
      • DCAWashington Ronald Reagan National Airport 09:59
        BDLHartford Bradley International Airport 12:15
      • BDLHartford Bradley International Airport 11:18
        ORDChicago O'Hare International Airport 13:55
      • 4h 56m (57m)
      • 1 Stop BDL · Hartford 57m
      • American Airlines (AA 4796)Embraer Emb 175
        American Airlines (AA 4141)Embraer 170
      • American Airlines (AA 4796)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 10:00 DCA
        13:45 ORD
        4Hrs, 45m 1 Stop (SYR)
      • DCAWashington Ronald Reagan National Airport 10:00 - ORD 13:45 4h 45m 1 Stop (SYR) Syracuse
      • DCAWashington Ronald Reagan National Airport 10:00
        SYRSyracuse Airport 12:24
      • SYRSyracuse Airport 11:34
        ORDChicago O'Hare International Airport 13:45
      • 4h 45m (50m)
      • 1 Stop SYR · Syracuse 50m
      • American Airlines (AA 5595)Crj 700 Canadair Regional
        American Airlines (AA 4134)Embraer 170
      • American Airlines (AA 5595)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 10:09 DCA
        14:12 ORD
        5Hrs, 03m 1 Stop (CLT)
      • DCAWashington Ronald Reagan National Airport 10:09 - ORD 14:12 5h 03m 1 Stop (CLT) Charlotte
      • DCAWashington Ronald Reagan National Airport 10:09
        CLTCharlotte Airport 13:04
      • CLTCharlotte Airport 12:02
        ORDChicago O'Hare International Airport 14:12
      • 5h 03m (1h 02m)
      • 1 Stop CLT · Charlotte 1h 02m
      • American Airlines (AA 966)Boeing 737 800
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 966)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 10:55 DCA
        15:10 MDW
        5Hrs, 15m 1 Stop (BNA)
      • DCAWashington Ronald Reagan National Airport 10:55 - MDW 15:10 5h 15m 1 Stop (BNA) Nashville
      • DCAWashington Ronald Reagan National Airport 10:55
        BNANashville Airport 13:35
      • BNANashville Airport 11:50
        MDWChicago Midway Airport 15:10
      • 5h 15m (1h 45m)
      • 1 Stop BNA · Nashville 1h 45m
      • Southwest Airlines (WN 1530)Boeing 737 800
        Southwest Airlines (WN 1622)Boeing 737 700
      • Southwest Airlines (WN 1530)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 11:05 BWI
        15:05 MDW
        5Hrs, 00m 1 Stop (RDU)
      • BWIBaltimore Washington International Airport 11:05 - MDW 15:05 5h 1 Stop (RDU) Morrisville
      • BWIBaltimore Washington International Airport 11:05
        RDURaleigh/Durham Airport 14:05
      • RDURaleigh/Durham Airport 12:20
        MDWChicago Midway Airport 15:05
      • 5h (1h 45m)
      • 1 Stop RDU · Morrisville 1h 45m
      • Southwest Airlines (WN 232)Boeing 737 700
        Southwest Airlines (WN 551)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 232)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 11:15 BWI
        14:35 MDW
        4Hrs, 20m 1 Stop (PIT)
      • BWIBaltimore Washington International Airport 11:15 - MDW 14:35 4h 20m 1 Stop (PIT) Pittsburgh
      • BWIBaltimore Washington International Airport 11:15
        PITPittsburgh International Airport 14:10
      • PITPittsburgh International Airport 12:20
        MDWChicago Midway Airport 14:35
      • 4h 20m (1h 50m)
      • 1 Stop PIT · Pittsburgh 1h 50m
      • Southwest Airlines (WN 4226)Boeing 737 700
        Southwest Airlines (WN 3286)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4226)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 11:40 BWI
        16:05 MDW
        5Hrs, 25m 1 Stop (CMH)
      • BWIBaltimore Washington International Airport 11:40 - MDW 16:05 5h 25m 1 Stop (CMH) Columbus
      • BWIBaltimore Washington International Airport 11:40
        CMHColumbus Port Columbus Intl Airport 15:50
      • CMHColumbus Port Columbus Intl Airport 13:05
        MDWChicago Midway Airport 16:05
      • 5h 25m (2h 45m)
      • 1 Stop CMH · Columbus 2h 45m
      • Southwest Airlines (WN 1296)Boeing 737 700
        Southwest Airlines (WN 2791)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1296)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:50 DCA
        16:20 MDW
        5Hrs, 30m 1 Stop (BNA)
      • DCAWashington Ronald Reagan National Airport 11:50 - MDW 16:20 5h 30m 1 Stop (BNA) Nashville
      • DCAWashington Ronald Reagan National Airport 11:50
        BNANashville Airport 14:45
      • BNANashville Airport 12:50
        MDWChicago Midway Airport 16:20
      • 5h 30m (1h 55m)
      • 1 Stop BNA · Nashville 1h 55m
      • Southwest Airlines (WN 2089)Boeing 737 700
        Southwest Airlines (WN 4066)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2089)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
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      What’s the fastest flight time from Washington to Chicago?

      The fastest flight time for direct flights from Washington to Chicago is 2 hours . Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Washington to Chicago?

      The most popular airline flying from Washington to Chicago is United Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Washington?

      The flight distance between Washington and Chicago is 955km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:59. The last flight of the day departs at 19:00. See the full list of flight times on Wego.

      How many airlines offer direct flights from Washington to Chicago?

      There are 4 airlines that offer direct flights from Washington to Chicago. Find out the list of airlines on Wego.

      Popular Airlines Flying From Washington to Chicago

      United Airlines ‏()
      American Airlines ‏()

      Popular Destinations From Chicago

      Popular Destinations From Washington

      Popular Hotels in Chicago

      Hotels In Popular Destinations