Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline American Airlines

The cheapest airline(s) flying from Jacksonville to Chicago is American Airlines.

  • American Airlines American Airlines
  • United Airlines United Airlines
  • Frontier Airlines Frontier Airlines
  • Southwest Airlines Southwest Airlines
  • JetBlue Airways JetBlue Airways
Cheapest Month December

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Jacksonville to Chicago is December.

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Wednesday

The cheapest day(s) of the week to fly from Jacksonville to Chicago is Wednesday.

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

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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      • Availability
        • M
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        • S
      • 20:35 JAX
        22:05 MDW
        2Hrs, 30m Direct
      • JAXJacksonville International Airport 20:35 - MDW 22:05 2h 30m Direct
      • JAXJacksonville International Airport 20:35
      • MDWChicago Midway Airport 22:05
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 2496)Boeing 737 800
      • Southwest Airlines (WN 2496)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 06:55 JAX
        08:42 ORD
        2Hrs, 47m Direct
      • JAXJacksonville International Airport 06:55 - ORD 08:42 2h 47m Direct
      • JAXJacksonville International Airport 06:55
      • ORDChicago O'Hare International Airport 08:42
      • 2h 47m
      • Direct
      • American Airlines (AA 3537)Embraer 170
      • American Airlines (AA 3537)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Embraer 170
      • 08:00 JAX
        09:38 ORD
        2Hrs, 38m Direct
      • JAXJacksonville International Airport 08:00 - ORD 09:38 2h 38m Direct
      • JAXJacksonville International Airport 08:00
      • ORDChicago O'Hare International Airport 09:38
      • 2h 38m
      • Direct
      • United Airlines (UA 1139)Boeing 737 700
      • United Airlines (UA 1139)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 700
      • 11:36 JAX
        13:15 ORD
        2Hrs, 39m Direct
      • JAXJacksonville International Airport 11:36 - ORD 13:15 2h 39m Direct
      • JAXJacksonville International Airport 11:36
      • ORDChicago O'Hare International Airport 13:15
      • 2h 39m
      • Direct
      • United Airlines (UA 2659)Boeing 737 700
      • United Airlines (UA 2659)
        • -
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        • -
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        • -
      • Boeing 737 700
      • 11:36 JAX
        13:15 ORD
        2Hrs, 39m Direct
      • JAXJacksonville International Airport 11:36 - ORD 13:15 2h 39m Direct
      • JAXJacksonville International Airport 11:36
      • ORDChicago O'Hare International Airport 13:15
      • 2h 39m
      • Direct
      • United Airlines (UA 2659)Airbus
      • United Airlines (UA 2659)
        • M
        • -
        • -
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        • F
        • -
        • S
      • Airbus
      • 12:48 JAX
        14:35 ORD
        2Hrs, 47m Direct
      • JAXJacksonville International Airport 12:48 - ORD 14:35 2h 47m Direct
      • JAXJacksonville International Airport 12:48
      • ORDChicago O'Hare International Airport 14:35
      • 2h 47m
      • Direct
      • American Airlines (AA 3533)Embraer Emb 175
      • American Airlines (AA 3533)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Embraer Emb 175
      • 12:48 JAX
        14:35 ORD
        2Hrs, 47m Direct
      • JAXJacksonville International Airport 12:48 - ORD 14:35 2h 47m Direct
      • JAXJacksonville International Airport 12:48
      • ORDChicago O'Hare International Airport 14:35
      • 2h 47m
      • Direct
      • American Airlines (AA 3533)Embraer 170
      • American Airlines (AA 3533)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Embraer 170
      • 16:00 JAX
        17:47 ORD
        2Hrs, 47m Direct
      • JAXJacksonville International Airport 16:00 - ORD 17:47 2h 47m Direct
      • JAXJacksonville International Airport 16:00
      • ORDChicago O'Hare International Airport 17:47
      • 2h 47m
      • Direct
      • American Airlines (AA 3533)Embraer 170
      • American Airlines (AA 3533)
        • -
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        • W
        • -
        • -
        • S
        • -
      • Embraer 170
      • 16:35 JAX
        18:05 MDW
        2Hrs, 30m Direct
      • JAXJacksonville International Airport 16:35 - MDW 18:05 2h 30m Direct
      • JAXJacksonville International Airport 16:35
      • MDWChicago Midway Airport 18:05
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 4816)Boeing 737 800
      • Southwest Airlines (WN 4816)
        • -
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        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 16:45 JAX
        18:23 ORD
        2Hrs, 38m Direct
      • JAXJacksonville International Airport 16:45 - ORD 18:23 2h 38m Direct
      • JAXJacksonville International Airport 16:45
      • ORDChicago O'Hare International Airport 18:23
      • 2h 38m
      • Direct
      • United Airlines (UA 2211)Boeing 737 700
      • United Airlines (UA 2211)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 16:45 JAX
        18:23 ORD
        2Hrs, 38m Direct
      • JAXJacksonville International Airport 16:45 - ORD 18:23 2h 38m Direct
      • JAXJacksonville International Airport 16:45
      • ORDChicago O'Hare International Airport 18:23
      • 2h 38m
      • Direct
      • United Airlines (UA 694)Airbus
      • United Airlines (UA 694)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus
      • 16:45 JAX
        18:23 ORD
        2Hrs, 38m Direct
      • JAXJacksonville International Airport 16:45 - ORD 18:23 2h 38m Direct
      • JAXJacksonville International Airport 16:45
      • ORDChicago O'Hare International Airport 18:23
      • 2h 38m
      • Direct
      • United Airlines (UA 694)Boeing 737 700
      • United Airlines (UA 694)
        • M
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        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 17:55 JAX
        19:25 MDW
        2Hrs, 30m Direct
      • JAXJacksonville International Airport 17:55 - MDW 19:25 2h 30m Direct
      • JAXJacksonville International Airport 17:55
      • MDWChicago Midway Airport 19:25
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 3032)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3032)
        • M
        • -
        • -
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        • F
        • -
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      • Boeing 737 Max 8 Passenger
      • 19:05 JAX
        22:20 MDW
        4Hrs, 15m 1 Stop (BNA)
      • JAXJacksonville International Airport 19:05 - MDW 22:20 4h 15m 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 19:05
        BNANashville Airport 20:45
      • BNANashville Airport 19:40
        MDWChicago Midway Airport 22:20
      • 4h 15m (1h 05m)
      • 1 Stop BNA · Nashville 1h 05m
      • Southwest Airlines (WN 3037)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1647)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3037)
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        • W
        • -
        • -
        • -
        • -
      • 19:06 JAX
        23:46 ORD
        5Hrs, 40m 1 Stop (PHL)
      • JAXJacksonville International Airport 19:06 - ORD 23:46 5h 40m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 19:06
        PHLPhiladelphia International Airport 22:20
      • PHLPhiladelphia International Airport 21:15
        ORDChicago O'Hare International Airport 23:46
      • 5h 40m (1h 05m)
      • 1 Stop PHL · Philadelphia 1h 05m
      • Frontier Airlines (F9 4022)Airbus A320 Neo
        Frontier Airlines (F9 2111)Airbus A321 Neo
      • Frontier Airlines (F9 4022)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 20:13 JAX
        00:16 ORD
        5Hrs, 03m 1 Stop (CLT)
      • JAXJacksonville International Airport 20:13 - ORD 00:16 5h 03m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 20:13
        CLTCharlotte Airport 22:56
      • CLTCharlotte Airport 21:38
        ORDChicago O'Hare International Airport 00:16
      • 5h 03m (1h 18m)
      • 1 Stop CLT · Charlotte 1h 18m
      • American Airlines (AA 1615)Airbus
        American Airlines (AA 1180)Boeing 737 800
      • American Airlines (AA 1615)
        • M
        • -
        • -
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        • F
        • -
        • S
      • 20:15 JAX
        23:10 MDW
        3Hrs, 55m 1 Stop (ATL)
      • JAXJacksonville International Airport 20:15 - MDW 23:10 3h 55m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 20:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:30
        MDWChicago Midway Airport 23:10
      • 3h 55m (45m)
      • 1 Stop ATL · Atlanta 45m
      • Southwest Airlines (WN 3965)Boeing 737 800
        Southwest Airlines (WN 4703)Boeing 737 800
      • Southwest Airlines (WN 3965)
        • M
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        • -
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        • F
        • -
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      • 21:00 JAX
        23:55 MDW
        3Hrs, 55m 1 Stop (BNA)
      • JAXJacksonville International Airport 21:00 - MDW 23:55 3h 55m 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 21:00
        BNANashville Airport 22:25
      • BNANashville Airport 21:35
        MDWChicago Midway Airport 23:55
      • 3h 55m (50m)
      • 1 Stop BNA · Nashville 50m
      • Southwest Airlines (WN 3037)Boeing 737 800
        Southwest Airlines (WN 1647)Boeing 737 700
      • Southwest Airlines (WN 3037)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 21:20 JAX
        00:25 MDW
        4Hrs, 05m 1 Stop (BNA)
      • JAXJacksonville International Airport 21:20 - MDW 00:25 4h 05m 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 21:20
        BNANashville Airport 22:50
      • BNANashville Airport 21:55
        MDWChicago Midway Airport 00:25
      • 4h 05m (55m)
      • 1 Stop BNA · Nashville 55m
      • Southwest Airlines (WN 1157)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1647)Boeing 737 800
      • Southwest Airlines (WN 1157)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 JAX
        08:42 ORD
        4Hrs, 42m 1 Stop (CLT)
      • JAXJacksonville International Airport 05:00 - ORD 08:42 4h 42m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 05:00
        CLTCharlotte Airport 07:34
      • CLTCharlotte Airport 06:24
        ORDChicago O'Hare International Airport 08:42
      • 4h 42m (1h 10m)
      • 1 Stop CLT · Charlotte 1h 10m
      • American Airlines (AA 548)Airbus
        American Airlines (AA 2843)Airbus
      • American Airlines (AA 548)
        • M
        • -
        • -
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        • F
        • S
        • S
      • 05:00 JAX
        10:48 ORD
        6Hrs, 48m 1 Stop (CLT)
      • JAXJacksonville International Airport 05:00 - ORD 10:48 6h 48m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 05:00
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 06:24
        ORDChicago O'Hare International Airport 10:48
      • 6h 48m (3h 09m)
      • 1 Stop CLT · Charlotte 3h 09m
      • American Airlines (AA 548)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 548)
        • M
        • -
        • -
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        • S
        • S
      • 05:19 JAX
        10:56 ORD
        6Hrs, 37m 1 Stop (DFW)
      • JAXJacksonville International Airport 05:19 - ORD 10:56 6h 37m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 05:19
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:19
        ORDChicago O'Hare International Airport 10:56
      • 6h 37m (1h 16m)
      • 1 Stop DFW · Dallas 1h 16m
      • American Airlines (AA 2789)Boeing 737 800
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2789)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • 05:19 JAX
        10:58 ORD
        6Hrs, 39m 1 Stop (DFW)
      • JAXJacksonville International Airport 05:19 - ORD 10:58 6h 39m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 05:19
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:19
        ORDChicago O'Hare International Airport 10:58
      • 6h 39m (1h 16m)
      • 1 Stop DFW · Dallas 1h 16m
      • American Airlines (AA 2789)Boeing 737 800
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2789)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 05:23 JAX
        10:56 ORD
        6Hrs, 33m 1 Stop (DFW)
      • JAXJacksonville International Airport 05:23 - ORD 10:56 6h 33m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 05:23
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:19
        ORDChicago O'Hare International Airport 10:56
      • 6h 33m (1h 16m)
      • 1 Stop DFW · Dallas 1h 16m
      • American Airlines (AA 2789)Airbus
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2789)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:23 JAX
        10:58 ORD
        6Hrs, 35m 1 Stop (DFW)
      • JAXJacksonville International Airport 05:23 - ORD 10:58 6h 35m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 05:23
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:19
        ORDChicago O'Hare International Airport 10:58
      • 6h 35m (1h 16m)
      • 1 Stop DFW · Dallas 1h 16m
      • American Airlines (AA 2789)Airbus
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2789)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 05:25 JAX
        10:00 MDW
        5Hrs, 35m 1 Stop (ATL)
      • JAXJacksonville International Airport 05:25 - MDW 10:00 5h 35m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 05:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:05
      • ATLAtlanta Hartsfield-Jackson Intl Airport 06:40
        MDWChicago Midway Airport 10:00
      • 5h 35m (2h 25m)
      • 1 Stop ATL · Atlanta 2h 25m
      • Southwest Airlines (WN 441)Boeing 737 700
        Southwest Airlines (WN 1432)Boeing 737 700
      • Southwest Airlines (WN 441)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:30 JAX
        10:10 MDW
        5Hrs, 40m 1 Stop (HOU)
      • JAXJacksonville International Airport 05:30 - MDW 10:10 5h 40m 1 Stop (HOU) Houston
      • JAXJacksonville International Airport 05:30
        HOUHouston Hobby Airport 07:45
      • HOUHouston Hobby Airport 07:05
        MDWChicago Midway Airport 10:10
      • 5h 40m (40m)
      • 1 Stop HOU · Houston 40m
      • Southwest Airlines (WN 575)Boeing 737 700
        Southwest Airlines (WN 2630)Boeing 737 700
      • Southwest Airlines (WN 575)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:55 JAX
        09:05 MDW
        4Hrs, 10m 1 Stop (ATL)
      • JAXJacksonville International Airport 05:55 - MDW 09:05 4h 10m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 05:55
        ATLAtlanta Hartsfield-Jackson Intl Airport 08:10
      • ATLAtlanta Hartsfield-Jackson Intl Airport 07:10
        MDWChicago Midway Airport 09:05
      • 4h 10m (1h)
      • 1 Stop ATL · Atlanta 1h
      • Southwest Airlines (WN 441)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1048)Boeing 737 700
      • Southwest Airlines (WN 441)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 JAX
        11:02 ORD
        6Hrs, 02m 1 Stop (MIA)
      • JAXJacksonville International Airport 06:00 - ORD 11:02 6h 02m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 06:00
        MIAMiami International Airport 08:31
      • MIAMiami International Airport 07:25
        ORDChicago O'Hare International Airport 11:02
      • 6h 02m (1h 06m)
      • 1 Stop MIA · Miami 1h 06m
      • American Airlines (AA 1160)Boeing 737 800
        American Airlines (AA 1431)Boeing 737 800
      • American Airlines (AA 1160)
        • M
        • -
        • -
        • -
        • F
        • S
        • S
      • 06:00 JAX
        11:03 ORD
        6Hrs, 03m 1 Stop (MIA)
      • JAXJacksonville International Airport 06:00 - ORD 11:03 6h 03m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 06:00
        MIAMiami International Airport 08:31
      • MIAMiami International Airport 07:25
        ORDChicago O'Hare International Airport 11:03
      • 6h 03m (1h 06m)
      • 1 Stop MIA · Miami 1h 06m
      • American Airlines (AA 1160)Boeing 737 800
        American Airlines (AA 1431)Boeing 737 800
      • American Airlines (AA 1160)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 JAX
        11:13 ORD
        6Hrs, 13m 1 Stop (PHL)
      • JAXJacksonville International Airport 06:00 - ORD 11:13 6h 13m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 06:00
        PHLPhiladelphia International Airport 09:42
      • PHLPhiladelphia International Airport 08:07
        ORDChicago O'Hare International Airport 11:13
      • 6h 13m (1h 35m)
      • 1 Stop PHL · Philadelphia 1h 35m
      • American Airlines (AA 1881)Airbus
        American Airlines (AA 2095)Boeing 737 800
      • American Airlines (AA 1881)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 JAX
        11:48 ORD
        6Hrs, 48m 1 Stop (MIA)
      • JAXJacksonville International Airport 06:00 - ORD 11:48 6h 48m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 06:00
        MIAMiami International Airport 09:18
      • MIAMiami International Airport 07:25
        ORDChicago O'Hare International Airport 11:48
      • 6h 48m (1h 53m)
      • 1 Stop MIA · Miami 1h 53m
      • American Airlines (AA 1160)Boeing 737 800
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 1160)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 JAX
        11:46 ORD
        6Hrs, 46m 1 Stop (MIA)
      • JAXJacksonville International Airport 06:00 - ORD 11:46 6h 46m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 06:00
        MIAMiami International Airport 09:15
      • MIAMiami International Airport 07:25
        ORDChicago O'Hare International Airport 11:46
      • 6h 46m (1h 50m)
      • 1 Stop MIA · Miami 1h 50m
      • American Airlines (AA 1160)Boeing 737 800
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 1160)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 JAX
        11:45 ORD
        6Hrs, 45m 1 Stop (MIA)
      • JAXJacksonville International Airport 06:00 - ORD 11:45 6h 45m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 06:00
        MIAMiami International Airport 09:15
      • MIAMiami International Airport 07:25
        ORDChicago O'Hare International Airport 11:45
      • 6h 45m (1h 50m)
      • 1 Stop MIA · Miami 1h 50m
      • American Airlines (AA 1160)Boeing 737 800
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 1160)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:10 JAX
        11:27 ORD
        6Hrs, 17m 1 Stop (BOS)
      • JAXJacksonville International Airport 06:10 - ORD 11:27 6h 17m 1 Stop (BOS) Boston
      • JAXJacksonville International Airport 06:10
        BOSBoston Logan International Airport 09:30
      • BOSBoston Logan International Airport 08:40
        ORDChicago O'Hare International Airport 11:27
      • 6h 17m (50m)
      • 1 Stop BOS · Boston 50m
      • JetBlue Airways (B6 1910)Embraer Emb E90
        JetBlue Airways (B6 311)Embraer Emb E90
      • JetBlue Airways (B6 1910)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 06:20 JAX
        11:20 MDW
        6Hrs, 00m 1 Stop (BNA)
      • JAXJacksonville International Airport 06:20 - MDW 11:20 6h 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 06:20
        BNANashville Airport 09:45
      • BNANashville Airport 07:05
        MDWChicago Midway Airport 11:20
      • 6h (2h 40m)
      • 1 Stop BNA · Nashville 2h 40m
      • Southwest Airlines (WN 699)Boeing 737 700
        Southwest Airlines (WN 4877)Boeing 737 700
      • Southwest Airlines (WN 699)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:22 JAX
        10:48 ORD
        5Hrs, 26m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:22 - ORD 10:48 5h 26m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:22
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 07:46
        ORDChicago O'Hare International Airport 10:48
      • 5h 26m (1h 47m)
      • 1 Stop CLT · Charlotte 1h 47m
      • American Airlines (AA 1973)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 1973)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 06:22 JAX
        10:50 ORD
        5Hrs, 28m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:22 - ORD 10:50 5h 28m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:22
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 07:46
        ORDChicago O'Hare International Airport 10:50
      • 5h 28m (1h 47m)
      • 1 Stop CLT · Charlotte 1h 47m
      • American Airlines (AA 1973)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 1973)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:22 JAX
        12:11 ORD
        6Hrs, 49m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:22 - ORD 12:11 6h 49m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:22
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 07:46
        ORDChicago O'Hare International Airport 12:11
      • 6h 49m (3h 13m)
      • 1 Stop CLT · Charlotte 3h 13m
      • American Airlines (AA 1973)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1973)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:44 JAX
        12:04 ORD
        6Hrs, 20m 1 Stop (EWR)
      • JAXJacksonville International Airport 06:44 - ORD 12:04 6h 20m 1 Stop (EWR) New York City
      • JAXJacksonville International Airport 06:44
        EWRNewark Liberty International Airport 10:30
      • EWRNewark Liberty International Airport 08:59
        ORDChicago O'Hare International Airport 12:04
      • 6h 20m (1h 31m)
      • 1 Stop EWR · New York City 1h 31m
      • United Airlines (UA 1666)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 1666)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:55 JAX
        10:10 MDW
        4Hrs, 15m 1 Stop (ATL)
      • JAXJacksonville International Airport 06:55 - MDW 10:10 4h 15m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 06:55
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:10
        MDWChicago Midway Airport 10:10
      • 4h 15m (1h 05m)
      • 1 Stop ATL · Atlanta 1h 05m
      • Southwest Airlines (WN 441)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1925)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 441)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:00 JAX
        11:49 ORD
        5Hrs, 49m 1 Stop (EWR)
      • JAXJacksonville International Airport 07:00 - ORD 11:49 5h 49m 1 Stop (EWR) New York City
      • JAXJacksonville International Airport 07:00
        EWRNewark Liberty International Airport 10:15
      • EWRNewark Liberty International Airport 09:15
        ORDChicago O'Hare International Airport 11:49
      • 5h 49m (1h)
      • 1 Stop EWR · New York City 1h
      • United Airlines (UA 1666)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 1666)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 07:00 JAX
        12:04 ORD
        6Hrs, 04m 1 Stop (EWR)
      • JAXJacksonville International Airport 07:00 - ORD 12:04 6h 04m 1 Stop (EWR) New York City
      • JAXJacksonville International Airport 07:00
        EWRNewark Liberty International Airport 10:30
      • EWRNewark Liberty International Airport 09:15
        ORDChicago O'Hare International Airport 12:04
      • 6h 04m (1h 15m)
      • 1 Stop EWR · New York City 1h 15m
      • United Airlines (UA 1666)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 1666)
        • M
        • T
        • W
        • T
        • -
        • -
        • -
      • 07:00 JAX
        12:04 ORD
        6Hrs, 04m 1 Stop (EWR)
      • JAXJacksonville International Airport 07:00 - ORD 12:04 6h 04m 1 Stop (EWR) New York City
      • JAXJacksonville International Airport 07:00
        EWRNewark Liberty International Airport 10:30
      • EWRNewark Liberty International Airport 09:15
        ORDChicago O'Hare International Airport 12:04
      • 6h 04m (1h 15m)
      • 1 Stop EWR · New York City 1h 15m
      • United Airlines (UA 1666)Boeing 737 Max 8 Passenger
        United Airlines (UA 1525)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1666)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:00 JAX
        12:25 ORD
        6Hrs, 25m 1 Stop (DFW)
      • JAXJacksonville International Airport 07:00 - ORD 12:25 6h 25m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 07:00
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 09:00
        ORDChicago O'Hare International Airport 12:25
      • 6h 25m (1h)
      • 1 Stop DFW · Dallas 1h
      • American Airlines (AA 375)Boeing 737 800
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 375)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:00 JAX
        12:25 ORD
        6Hrs, 25m 1 Stop (DFW)
      • JAXJacksonville International Airport 07:00 - ORD 12:25 6h 25m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 07:00
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:56
        ORDChicago O'Hare International Airport 12:25
      • 6h 25m (1h 04m)
      • 1 Stop DFW · Dallas 1h 04m
      • American Airlines (AA 375)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 375)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 07:00 JAX
        12:29 ORD
        6Hrs, 29m 1 Stop (DFW)
      • JAXJacksonville International Airport 07:00 - ORD 12:29 6h 29m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 07:00
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:56
        ORDChicago O'Hare International Airport 12:29
      • 6h 29m (1h 04m)
      • 1 Stop DFW · Dallas 1h 04m
      • American Airlines (AA 375)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 375)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:00 JAX
        12:31 ORD
        6Hrs, 31m 1 Stop (IAH)
      • JAXJacksonville International Airport 07:00 - ORD 12:31 6h 31m 1 Stop (IAH) Houston
      • JAXJacksonville International Airport 07:00
        IAHHouston George Bush Intercontinental Airport 09:49
      • IAHHouston George Bush Intercontinental Airport 08:33
        ORDChicago O'Hare International Airport 12:31
      • 6h 31m (1h 16m)
      • 1 Stop IAH · Houston 1h 16m
      • United Airlines (UA 2453)Airbus
        United Airlines (UA 1321)Boeing 737 900
      • United Airlines (UA 2453)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 07:15 JAX
        12:24 ORD
        6Hrs, 09m 1 Stop (PHL)
      • JAXJacksonville International Airport 07:15 - ORD 12:24 6h 09m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 07:15
        PHLPhiladelphia International Airport 10:46
      • PHLPhiladelphia International Airport 09:22
        ORDChicago O'Hare International Airport 12:24
      • 6h 09m (1h 24m)
      • 1 Stop PHL · Philadelphia 1h 24m
      • American Airlines (AA 709)Airbus
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 709)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:15 JAX
        12:25 ORD
        6Hrs, 10m 1 Stop (PHL)
      • JAXJacksonville International Airport 07:15 - ORD 12:25 6h 10m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 07:15
        PHLPhiladelphia International Airport 10:50
      • PHLPhiladelphia International Airport 09:22
        ORDChicago O'Hare International Airport 12:25
      • 6h 10m (1h 28m)
      • 1 Stop PHL · Philadelphia 1h 28m
      • American Airlines (AA 709)Airbus
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 709)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • 07:15 JAX
        12:25 ORD
        6Hrs, 10m 1 Stop (PHL)
      • JAXJacksonville International Airport 07:15 - ORD 12:25 6h 10m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 07:15
        PHLPhiladelphia International Airport 10:46
      • PHLPhiladelphia International Airport 09:22
        ORDChicago O'Hare International Airport 12:25
      • 6h 10m (1h 24m)
      • 1 Stop PHL · Philadelphia 1h 24m
      • American Airlines (AA 709)Airbus
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 709)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 07:20 JAX
        12:15 MDW
        5Hrs, 55m 1 Stop (BNA)
      • JAXJacksonville International Airport 07:20 - MDW 12:15 5h 55m 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 07:20
        BNANashville Airport 10:35
      • BNANashville Airport 07:55
        MDWChicago Midway Airport 12:15
      • 5h 55m (2h 40m)
      • 1 Stop BNA · Nashville 2h 40m
      • Southwest Airlines (WN 699)Boeing 737 700
        Southwest Airlines (WN 4877)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 699)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:20 JAX
        13:00 ORD
        6Hrs, 40m 1 Stop (BNA)
      • JAXJacksonville International Airport 07:20 - ORD 13:00 6h 40m 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 07:20
        BNANashville Airport 11:15
      • BNANashville Airport 07:55
        ORDChicago O'Hare International Airport 13:00
      • 6h 40m (3h 20m)
      • 1 Stop BNA · Nashville 3h 20m
      • Southwest Airlines (WN 699)Boeing 737 700
        Southwest Airlines (WN 983)Boeing 737 800
      • Southwest Airlines (WN 699)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:24 JAX
        13:12 ORD
        6Hrs, 48m 1 Stop (DCA)
      • JAXJacksonville International Airport 07:24 - ORD 13:12 6h 48m 1 Stop (DCA) Washington
      • JAXJacksonville International Airport 07:24
        DCAWashington Ronald Reagan National Airport 11:59
      • DCAWashington Ronald Reagan National Airport 09:20
        ORDChicago O'Hare International Airport 13:12
      • 6h 48m (2h 39m)
      • 1 Stop DCA · Washington 2h 39m
      • American Airlines (AA 5379)Canadair Regional
        American Airlines (AA 489)Airbus
      • American Airlines (AA 5379)
        • M
        • -
        • -
        • T
        • F
        • S
        • -
      • 07:26 JAX
        13:12 ORD
        6Hrs, 46m 1 Stop (DCA)
      • JAXJacksonville International Airport 07:26 - ORD 13:12 6h 46m 1 Stop (DCA) Washington
      • JAXJacksonville International Airport 07:26
        DCAWashington Ronald Reagan National Airport 11:59
      • DCAWashington Ronald Reagan National Airport 09:20
        ORDChicago O'Hare International Airport 13:12
      • 6h 46m (2h 39m)
      • 1 Stop DCA · Washington 2h 39m
      • American Airlines (AA 5091)Crj 700 Canadair Regional
        American Airlines (AA 489)Airbus
      • American Airlines (AA 5091)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 09:25 JAX
        14:19 ORD
        5Hrs, 54m 1 Stop (IAD)
      • JAXJacksonville International Airport 09:25 - ORD 14:19 5h 54m 1 Stop (IAD) Washington
      • JAXJacksonville International Airport 09:25
        IADWashington Dulles International Airport 13:05
      • IADWashington Dulles International Airport 11:15
        ORDChicago O'Hare International Airport 14:19
      • 5h 54m (1h 50m)
      • 1 Stop IAD · Washington 1h 50m
      • United Airlines (UA 1267)Boeing 737 800
        United Airlines (UA 673)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1267)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 09:25 JAX
        14:19 ORD
        5Hrs, 54m 1 Stop (IAD)
      • JAXJacksonville International Airport 09:25 - ORD 14:19 5h 54m 1 Stop (IAD) Washington
      • JAXJacksonville International Airport 09:25
        IADWashington Dulles International Airport 13:05
      • IADWashington Dulles International Airport 11:15
        ORDChicago O'Hare International Airport 14:19
      • 5h 54m (1h 50m)
      • 1 Stop IAD · Washington 1h 50m
      • United Airlines (UA 1267)Boeing 737 800
        United Airlines (UA 673)Boeing 737 800
      • United Airlines (UA 1267)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 09:36 JAX
        13:10 ORD
        4Hrs, 34m 1 Stop (CLT)
      • JAXJacksonville International Airport 09:36 - ORD 13:10 4h 34m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 09:36
        CLTCharlotte Airport 11:40
      • CLTCharlotte Airport 11:00
        ORDChicago O'Hare International Airport 13:10
      • 4h 34m (40m)
      • 1 Stop CLT · Charlotte 40m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1919)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 09:36 JAX
        14:10 ORD
        5Hrs, 34m 1 Stop (CLT)
      • JAXJacksonville International Airport 09:36 - ORD 14:10 5h 34m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 09:36
        CLTCharlotte Airport 13:00
      • CLTCharlotte Airport 11:00
        ORDChicago O'Hare International Airport 14:10
      • 5h 34m (2h)
      • 1 Stop CLT · Charlotte 2h
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 1919)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 09:36 JAX
        14:15 ORD
        5Hrs, 39m 1 Stop (CLT)
      • JAXJacksonville International Airport 09:36 - ORD 14:15 5h 39m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 09:36
        CLTCharlotte Airport 13:07
      • CLTCharlotte Airport 11:00
        ORDChicago O'Hare International Airport 14:15
      • 5h 39m (2h 07m)
      • 1 Stop CLT · Charlotte 2h 07m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 1919)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 09:36 JAX
        14:17 ORD
        5Hrs, 41m 1 Stop (CLT)
      • JAXJacksonville International Airport 09:36 - ORD 14:17 5h 41m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 09:36
        CLTCharlotte Airport 13:07
      • CLTCharlotte Airport 11:00
        ORDChicago O'Hare International Airport 14:17
      • 5h 41m (2h 07m)
      • 1 Stop CLT · Charlotte 2h 07m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 1919)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 09:36 JAX
        14:24 ORD
        5Hrs, 48m 1 Stop (CLT)
      • JAXJacksonville International Airport 09:36 - ORD 14:24 5h 48m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 09:36
        CLTCharlotte Airport 13:16
      • CLTCharlotte Airport 11:00
        ORDChicago O'Hare International Airport 14:24
      • 5h 48m (2h 16m)
      • 1 Stop CLT · Charlotte 2h 16m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 1919)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 10:35 JAX
        15:09 ORD
        5Hrs, 34m 1 Stop (PHL)
      • JAXJacksonville International Airport 10:35 - ORD 15:09 5h 34m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 10:35
        PHLPhiladelphia International Airport 13:41
      • PHLPhiladelphia International Airport 12:39
        ORDChicago O'Hare International Airport 15:09
      • 5h 34m (1h 02m)
      • 1 Stop PHL · Philadelphia 1h 02m
      • American Airlines (AA 5458)Canadair Regional
        American Airlines (AA 470)Airbus
      • American Airlines (AA 5458)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
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      What’s the fastest flight time from Jacksonville to Chicago?

      The fastest flight time for direct flights from Jacksonville to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.

      How far is Chicago from Jacksonville?

      The flight distance between Jacksonville and Chicago is 1391km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

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

      How many airlines offer direct flights from Jacksonville to Chicago?

      There are 3 airlines that offer direct flights from Jacksonville to Chicago. Find out the list of airlines on Wego.

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