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
  • Southwest Airlines Southwest Airlines
  • JetBlue Airways JetBlue Airways
Cheapest Month March

Travel Period: January 2025 - December 2025

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

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

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

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

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

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      • Availability
        • M
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      • 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
      • 06:00 JAX
        07:46 ORD
        2Hrs, 46m Direct
      • JAXJacksonville International Airport 06:00 - ORD 07:46 2h 46m Direct
      • JAXJacksonville International Airport 06:00
      • ORDChicago O'Hare International Airport 07:46
      • 2h 46m
      • Direct
      • United Airlines (UA 1139)Airbus
      • United Airlines (UA 1139)
        • M
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        • -
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      • Airbus
      • 06:00 JAX
        07:46 ORD
        2Hrs, 46m Direct
      • JAXJacksonville International Airport 06:00 - ORD 07:46 2h 46m Direct
      • JAXJacksonville International Airport 06:00
      • ORDChicago O'Hare International Airport 07:46
      • 2h 46m
      • Direct
      • United Airlines (UA 1139)Boeing 737 800
      • United Airlines (UA 1139)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 06:04 JAX
        07:51 ORD
        2Hrs, 47m Direct
      • JAXJacksonville International Airport 06:04 - ORD 07:51 2h 47m Direct
      • JAXJacksonville International Airport 06:04
      • ORDChicago O'Hare International Airport 07:51
      • 2h 47m
      • Direct
      • American Airlines (AA 1826)Boeing 737 800
      • American Airlines (AA 1826)
        • -
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        • S
        • S
      • Boeing 737 800
      • 06:10 JAX
        07:52 ORD
        2Hrs, 42m Direct
      • JAXJacksonville International Airport 06:10 - ORD 07:52 2h 42m Direct
      • JAXJacksonville International Airport 06:10
      • ORDChicago O'Hare International Airport 07:52
      • 2h 42m
      • Direct
      • American Airlines (AA 3474)Embraer 170
      • American Airlines (AA 3474)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Embraer 170
      • 06:15 JAX
        07:57 ORD
        2Hrs, 42m Direct
      • JAXJacksonville International Airport 06:15 - ORD 07:57 2h 42m Direct
      • JAXJacksonville International Airport 06:15
      • ORDChicago O'Hare International Airport 07:57
      • 2h 42m
      • Direct
      • American Airlines (AA 3474)Embraer 170
      • American Airlines (AA 3474)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Embraer 170
      • 10:43 JAX
        12:28 ORD
        2Hrs, 45m Direct
      • JAXJacksonville International Airport 10:43 - ORD 12:28 2h 45m Direct
      • JAXJacksonville International Airport 10:43
      • ORDChicago O'Hare International Airport 12:28
      • 2h 45m
      • Direct
      • United Airlines (UA 472)Boeing 737 700
      • United Airlines (UA 472)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 11:59 JAX
        13:52 ORD
        2Hrs, 53m Direct
      • JAXJacksonville International Airport 11:59 - ORD 13:52 2h 53m Direct
      • JAXJacksonville International Airport 11:59
      • ORDChicago O'Hare International Airport 13:52
      • 2h 53m
      • Direct
      • United Airlines (UA 3566)Embraer 175
      • United Airlines (UA 3566)
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        • -
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      • Embraer 175
      • 12:00 JAX
        13:25 MDW
        2Hrs, 25m Direct
      • JAXJacksonville International Airport 12:00 - MDW 13:25 2h 25m Direct
      • JAXJacksonville International Airport 12:00
      • MDWChicago Midway Airport 13:25
      • 2h 25m
      • Direct
      • Southwest Airlines (WN 4423)Boeing 737 800
      • Southwest Airlines (WN 4423)
        • M
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        • -
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        • F
        • -
        • S
      • Boeing 737 800
      • 12:27 JAX
        14:08 ORD
        2Hrs, 41m Direct
      • JAXJacksonville International Airport 12:27 - ORD 14:08 2h 41m Direct
      • JAXJacksonville International Airport 12:27
      • ORDChicago O'Hare International Airport 14:08
      • 2h 41m
      • Direct
      • American Airlines (AA 3968)Embraer 170
      • American Airlines (AA 3968)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer 170
      • 12:30 JAX
        14:12 ORD
        2Hrs, 42m Direct
      • JAXJacksonville International Airport 12:30 - ORD 14:12 2h 42m Direct
      • JAXJacksonville International Airport 12:30
      • ORDChicago O'Hare International Airport 14:12
      • 2h 42m
      • Direct
      • American Airlines (AA 3968)Embraer 170
      • American Airlines (AA 3968)
        • M
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        • -
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        • -
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      • Embraer 170
      • 15:25 JAX
        17:10 ORD
        2Hrs, 45m Direct
      • JAXJacksonville International Airport 15:25 - ORD 17:10 2h 45m Direct
      • JAXJacksonville International Airport 15:25
      • ORDChicago O'Hare International Airport 17:10
      • 2h 45m
      • Direct
      • United Airlines (UA 457)Boeing 737 800
      • United Airlines (UA 457)
        • M
        • -
        • -
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        • F
        • S
        • S
      • Boeing 737 800
      • 15:25 JAX
        17:10 ORD
        2Hrs, 45m Direct
      • JAXJacksonville International Airport 15:25 - ORD 17:10 2h 45m Direct
      • JAXJacksonville International Airport 15:25
      • ORDChicago O'Hare International Airport 17:10
      • 2h 45m
      • Direct
      • United Airlines (UA 457)Boeing 737 700
      • United Airlines (UA 457)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 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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        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 19:00 JAX
        23:55 MDW
        5Hrs, 55m 1 Stop (STL)
      • JAXJacksonville International Airport 19:00 - MDW 23:55 5h 55m 1 Stop (STL) Saint Louis
      • JAXJacksonville International Airport 19:00
        STLSt Louis Lambert Intl Airport 22:45
      • STLSt Louis Lambert Intl Airport 20:15
        MDWChicago Midway Airport 23:55
      • 5h 55m (2h 30m)
      • 1 Stop STL · Saint Louis 2h 30m
      • Southwest Airlines (WN 2151)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 652)Boeing 737 700
      • Southwest Airlines (WN 2151)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 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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        • -
        • -
        • -
        • -
      • 20:45 JAX
        23:40 MDW
        3Hrs, 55m 1 Stop (ATL)
      • JAXJacksonville International Airport 20:45 - MDW 23:40 3h 55m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 20:45
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:45
      • ATLAtlanta Hartsfield-Jackson Intl Airport 22:00
        MDWChicago Midway Airport 23:40
      • 3h 55m (45m)
      • 1 Stop ATL · Atlanta 45m
      • Southwest Airlines (WN 441)Boeing 737 800
        Southwest Airlines (WN 598)Boeing 737 700
      • Southwest Airlines (WN 441)
        • M
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        • -
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      • 21:20 JAX
        00:20 MDW
        4Hrs, 00m 1 Stop (BNA)
      • JAXJacksonville International Airport 21:20 - MDW 00:20 4h 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 21:20
        BNANashville Airport 22:45
      • BNANashville Airport 21:55
        MDWChicago Midway Airport 00:20
      • 4h (50m)
      • 1 Stop BNA · Nashville 50m
      • Southwest Airlines (WN 3037)Boeing 737 800
        Southwest Airlines (WN 2804)Boeing 737 Max 8 Passenger
      • 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
        08:55 ORD
        4Hrs, 55m 1 Stop (CLT)
      • JAXJacksonville International Airport 05:00 - ORD 08:55 4h 55m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 05:00
        CLTCharlotte Airport 07:44
      • CLTCharlotte Airport 06:26
        ORDChicago O'Hare International Airport 08:55
      • 4h 55m (1h 18m)
      • 1 Stop CLT · Charlotte 1h 18m
      • American Airlines (AA 548)Airbus
        American Airlines (AA 2843)Airbus
      • American Airlines (AA 548)
        • M
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        • -
        • T
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        • S
      • 05:00 JAX
        10:42 ORD
        6Hrs, 42m 1 Stop (DFW)
      • JAXJacksonville International Airport 05:00 - ORD 10:42 6h 42m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:14
      • DFWDallas/Fort Worth Intl Airport 06:59
        ORDChicago O'Hare International Airport 10:42
      • 6h 42m (1h 15m)
      • 1 Stop DFW · Dallas 1h 15m
      • American Airlines (AA 3198)Boeing 737 800
        American Airlines (AA 328)Boeing 737 800
      • American Airlines (AA 3198)
        • -
        • -
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        • -
        • -
        • -
        • -
      • 05:00 JAX
        10:35 ORD
        6Hrs, 35m 1 Stop (DFW)
      • JAXJacksonville International Airport 05:00 - ORD 10:35 6h 35m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:14
      • DFWDallas/Fort Worth Intl Airport 06:59
        ORDChicago O'Hare International Airport 10:35
      • 6h 35m (1h 15m)
      • 1 Stop DFW · Dallas 1h 15m
      • American Airlines (AA 3198)Boeing 737 800
        American Airlines (AA 328)Airbus
      • American Airlines (AA 3198)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • 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
        09:00 MDW
        4Hrs, 30m 1 Stop (ATL)
      • JAXJacksonville International Airport 05:30 - MDW 09:00 4h 30m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 05:30
        ATLAtlanta Hartsfield-Jackson Intl Airport 08:05
      • ATLAtlanta Hartsfield-Jackson Intl Airport 06:45
        MDWChicago Midway Airport 09:00
      • 4h 30m (1h 20m)
      • 1 Stop ATL · Atlanta 1h 20m
      • Southwest Airlines (WN 3965)Boeing 737 700
        Southwest Airlines (WN 1336)Boeing 737 800
      • Southwest Airlines (WN 3965)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:30 JAX
        09:05 MDW
        4Hrs, 35m 1 Stop (ATL)
      • JAXJacksonville International Airport 05:30 - MDW 09:05 4h 35m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 05:30
        ATLAtlanta Hartsfield-Jackson Intl Airport 08:10
      • ATLAtlanta Hartsfield-Jackson Intl Airport 06:45
        MDWChicago Midway Airport 09:05
      • 4h 35m (1h 25m)
      • 1 Stop ATL · Atlanta 1h 25m
      • Southwest Airlines (WN 3965)Boeing 737 700
        Southwest Airlines (WN 1336)Boeing 737 800
      • Southwest Airlines (WN 3965)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 JAX
        10:20 MDW
        5Hrs, 20m 1 Stop (BNA)
      • JAXJacksonville International Airport 06:00 - MDW 10:20 5h 20m 1 Stop (BNA) Nashville
      • JAXJacksonville International Airport 06:00
        BNANashville Airport 08:45
      • BNANashville Airport 06:40
        MDWChicago Midway Airport 10:20
      • 5h 20m (2h 05m)
      • 1 Stop BNA · Nashville 2h 05m
      • Southwest Airlines (WN 3170)Boeing 737 700
        Southwest Airlines (WN 6342)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3170)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 JAX
        10:46 ORD
        5Hrs, 46m 1 Stop (MIA)
      • JAXJacksonville International Airport 06:00 - ORD 10:46 5h 46m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 06:00
        MIAMiami International Airport 08:20
      • MIAMiami International Airport 07:19
        ORDChicago O'Hare International Airport 10:46
      • 5h 46m (1h 01m)
      • 1 Stop MIA · Miami 1h 01m
      • American Airlines (AA 3489)Embraer Emb 175
        American Airlines (AA 1431)Boeing 737 800
      • American Airlines (AA 3489)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:00 JAX
        11:44 ORD
        6Hrs, 44m 1 Stop (MIA)
      • JAXJacksonville International Airport 06:00 - ORD 11:44 6h 44m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 06:00
        MIAMiami International Airport 09:12
      • MIAMiami International Airport 07:19
        ORDChicago O'Hare International Airport 11:44
      • 6h 44m (1h 53m)
      • 1 Stop MIA · Miami 1h 53m
      • American Airlines (AA 3489)Embraer Emb 175
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 3489)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:05 JAX
        11:30 ORD
        6Hrs, 25m 1 Stop (DFW)
      • JAXJacksonville International Airport 06:05 - ORD 11:30 6h 25m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 06:05
        DFWDallas/Fort Worth Intl Airport 08:59
      • DFWDallas/Fort Worth Intl Airport 08:04
        ORDChicago O'Hare International Airport 11:30
      • 6h 25m (55m)
      • 1 Stop DFW · Dallas 55m
      • American Airlines (AA 2789)Boeing 737 800
        American Airlines (AA 3191)Boeing 737 800
      • American Airlines (AA 2789)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:05 JAX
        11:30 ORD
        6Hrs, 25m 1 Stop (DFW)
      • JAXJacksonville International Airport 06:05 - ORD 11:30 6h 25m 1 Stop (DFW) Dallas
      • JAXJacksonville International Airport 06:05
        DFWDallas/Fort Worth Intl Airport 09:04
      • DFWDallas/Fort Worth Intl Airport 08:04
        ORDChicago O'Hare International Airport 11:30
      • 6h 25m (1h)
      • 1 Stop DFW · Dallas 1h
      • American Airlines (AA 2789)Boeing 737 800
        American Airlines (AA 3191)Boeing 737 800
      • American Airlines (AA 2789)
        • M
        • T
        • -
        • T
        • F
        • -
        • S
      • 06:20 JAX
        10:10 MDW
        4Hrs, 50m 1 Stop (ATL)
      • JAXJacksonville International Airport 06:20 - MDW 10:10 4h 50m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 06:20
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 07:40
        MDWChicago Midway Airport 10:10
      • 4h 50m (1h 35m)
      • 1 Stop ATL · Atlanta 1h 35m
      • Southwest Airlines (WN 441)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1925)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 441)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:29 JAX
        11:01 ORD
        5Hrs, 32m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:29 - ORD 11:01 5h 32m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:29
        CLTCharlotte Airport 09:40
      • CLTCharlotte Airport 07:56
        ORDChicago O'Hare International Airport 11:01
      • 5h 32m (1h 44m)
      • 1 Stop CLT · Charlotte 1h 44m
      • American Airlines (AA 1973)Airbus A321 Neo
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 1973)
        • M
        • T
        • -
        • -
        • F
        • S
        • S
      • 06:29 JAX
        11:01 ORD
        5Hrs, 32m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:29 - ORD 11:01 5h 32m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:29
        CLTCharlotte Airport 09:40
      • CLTCharlotte Airport 07:55
        ORDChicago O'Hare International Airport 11:01
      • 5h 32m (1h 45m)
      • 1 Stop CLT · Charlotte 1h 45m
      • American Airlines (AA 1973)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 1973)
        • -
        • -
        • W
        • T
        • -
        • -
        • -
      • 06:29 JAX
        12:07 ORD
        6Hrs, 38m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:29 - ORD 12:07 6h 38m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:29
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 07:56
        ORDChicago O'Hare International Airport 12:07
      • 6h 38m (3h 03m)
      • 1 Stop CLT · Charlotte 3h 03m
      • American Airlines (AA 1973)Airbus A321 Neo
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1973)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:29 JAX
        12:12 ORD
        6Hrs, 43m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:29 - ORD 12:12 6h 43m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:29
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 07:55
        ORDChicago O'Hare International Airport 12:12
      • 6h 43m (3h 06m)
      • 1 Stop CLT · Charlotte 3h 06m
      • American Airlines (AA 1973)Airbus
        American Airlines (AA 2279)Airbus A321 Neo
      • American Airlines (AA 1973)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:29 JAX
        12:12 ORD
        6Hrs, 43m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:29 - ORD 12:12 6h 43m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:29
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 07:55
        ORDChicago O'Hare International Airport 12:12
      • 6h 43m (3h 06m)
      • 1 Stop CLT · Charlotte 3h 06m
      • American Airlines (AA 1973)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1973)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:29 JAX
        12:12 ORD
        6Hrs, 43m 1 Stop (CLT)
      • JAXJacksonville International Airport 06:29 - ORD 12:12 6h 43m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 06:29
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 07:56
        ORDChicago O'Hare International Airport 12:12
      • 6h 43m (3h 05m)
      • 1 Stop CLT · Charlotte 3h 05m
      • American Airlines (AA 1973)Airbus A321 Neo
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1973)
        • M
        • T
        • -
        • -
        • F
        • -
        • S
      • 06:35 JAX
        11:38 ORD
        6Hrs, 03m 1 Stop (EWR)
      • JAXJacksonville International Airport 06:35 - ORD 11:38 6h 03m 1 Stop (EWR) New York City
      • JAXJacksonville International Airport 06:35
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 08:57
        ORDChicago O'Hare International Airport 11:38
      • 6h 03m (1h 03m)
      • 1 Stop EWR · New York City 1h 03m
      • United Airlines (UA 1666)Boeing 737 900
        United Airlines (UA 1525)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1666)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:35 JAX
        11:38 ORD
        6Hrs, 03m 1 Stop (EWR)
      • JAXJacksonville International Airport 06:35 - ORD 11:38 6h 03m 1 Stop (EWR) New York City
      • JAXJacksonville International Airport 06:35
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 08:57
        ORDChicago O'Hare International Airport 11:38
      • 6h 03m (1h 03m)
      • 1 Stop EWR · New York City 1h 03m
      • United Airlines (UA 1666)Boeing 737 900
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 1666)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • 06:45 JAX
        10:10 MDW
        4Hrs, 25m 1 Stop (ATL)
      • JAXJacksonville International Airport 06:45 - MDW 10:10 4h 25m 1 Stop (ATL) Atlanta
      • JAXJacksonville International Airport 06:45
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:00
        MDWChicago Midway Airport 10:10
      • 4h 25m (1h 15m)
      • 1 Stop ATL · Atlanta 1h 15m
      • Southwest Airlines (WN 441)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1925)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 441)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:00 JAX
        12:15 ORD
        6Hrs, 15m 1 Stop (PHL)
      • JAXJacksonville International Airport 07:00 - ORD 12:15 6h 15m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 07:00
        PHLPhiladelphia International Airport 10:41
      • PHLPhiladelphia International Airport 09:09
        ORDChicago O'Hare International Airport 12:15
      • 6h 15m (1h 32m)
      • 1 Stop PHL · Philadelphia 1h 32m
      • American Airlines (AA 709)Airbus
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 709)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 07:00 JAX
        12:16 ORD
        6Hrs, 16m 1 Stop (IAH)
      • JAXJacksonville International Airport 07:00 - ORD 12:16 6h 16m 1 Stop (IAH) Houston
      • JAXJacksonville International Airport 07:00
        IAHHouston George Bush Intercontinental Airport 09:30
      • IAHHouston George Bush Intercontinental Airport 08:38
        ORDChicago O'Hare International Airport 12:16
      • 6h 16m (52m)
      • 1 Stop IAH · Houston 52m
      • United Airlines (UA 2453)Boeing 737 800
        United Airlines (UA 2124)Boeing 737 800
      • United Airlines (UA 2453)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:00 JAX
        12:16 ORD
        6Hrs, 16m 1 Stop (IAH)
      • JAXJacksonville International Airport 07:00 - ORD 12:16 6h 16m 1 Stop (IAH) Houston
      • JAXJacksonville International Airport 07:00
        IAHHouston George Bush Intercontinental Airport 09:30
      • IAHHouston George Bush Intercontinental Airport 08:38
        ORDChicago O'Hare International Airport 12:16
      • 6h 16m (52m)
      • 1 Stop IAH · Houston 52m
      • United Airlines (UA 2453)Boeing 737 800
        United Airlines (UA 2124)Boeing 737 900
      • United Airlines (UA 2453)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
      • 07:05 JAX
        11:44 ORD
        5Hrs, 39m 1 Stop (MIA)
      • JAXJacksonville International Airport 07:05 - ORD 11:44 5h 39m 1 Stop (MIA) Miami
      • JAXJacksonville International Airport 07:05
        MIAMiami International Airport 09:12
      • MIAMiami International Airport 08:31
        ORDChicago O'Hare International Airport 11:44
      • 5h 39m (41m)
      • 1 Stop MIA · Miami 41m
      • American Airlines (AA 2291)Boeing 737 Max 8 Passenger
        American Airlines (AA 2174)Boeing 737 800
      • American Airlines (AA 2291)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 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
        • -
        • -
        • -
        • -
      • 07:29 JAX
        13:14 ORD
        6Hrs, 45m 1 Stop (DCA)
      • JAXJacksonville International Airport 07:29 - ORD 13:14 6h 45m 1 Stop (DCA) Washington
      • JAXJacksonville International Airport 07:29
        DCAWashington Ronald Reagan National Airport 11:54
      • DCAWashington Ronald Reagan National Airport 09:20
        ORDChicago O'Hare International Airport 13:14
      • 6h 45m (2h 34m)
      • 1 Stop DCA · Washington 2h 34m
      • American Airlines (AA 4446)Embraer Emb 175
        American Airlines (AA 489)Airbus
      • American Airlines (AA 4446)
        • M
        • -
        • -
        • T
        • F
        • S
        • -
      • 07:34 JAX
        13:14 ORD
        6Hrs, 40m 1 Stop (DCA)
      • JAXJacksonville International Airport 07:34 - ORD 13:14 6h 40m 1 Stop (DCA) Washington
      • JAXJacksonville International Airport 07:34
        DCAWashington Ronald Reagan National Airport 11:54
      • DCAWashington Ronald Reagan National Airport 09:29
        ORDChicago O'Hare International Airport 13:14
      • 6h 40m (2h 25m)
      • 1 Stop DCA · Washington 2h 25m
      • American Airlines (AA 2093)Airbus
        American Airlines (AA 489)Airbus
      • American Airlines (AA 2093)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:44 JAX
        11:01 ORD
        4Hrs, 17m 1 Stop (CLT)
      • JAXJacksonville International Airport 07:44 - ORD 11:01 4h 17m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 07:44
        CLTCharlotte Airport 09:40
      • CLTCharlotte Airport 09:10
        ORDChicago O'Hare International Airport 11:01
      • 4h 17m (30m)
      • 1 Stop CLT · Charlotte 30m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 1919)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 07:44 JAX
        12:07 ORD
        5Hrs, 23m 1 Stop (CLT)
      • JAXJacksonville International Airport 07:44 - ORD 12:07 5h 23m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 07:44
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 09:10
        ORDChicago O'Hare International Airport 12:07
      • 5h 23m (1h 49m)
      • 1 Stop CLT · Charlotte 1h 49m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1919)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:44 JAX
        12:12 ORD
        5Hrs, 28m 1 Stop (CLT)
      • JAXJacksonville International Airport 07:44 - ORD 12:12 5h 28m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 07:44
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 09:10
        ORDChicago O'Hare International Airport 12:12
      • 5h 28m (1h 51m)
      • 1 Stop CLT · Charlotte 1h 51m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 2279)Airbus A321 Neo
      • American Airlines (AA 1919)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 07:44 JAX
        12:12 ORD
        5Hrs, 28m 1 Stop (CLT)
      • JAXJacksonville International Airport 07:44 - ORD 12:12 5h 28m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 07:44
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 09:10
        ORDChicago O'Hare International Airport 12:12
      • 5h 28m (1h 51m)
      • 1 Stop CLT · Charlotte 1h 51m
      • American Airlines (AA 1919)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1919)
        • M
        • T
        • -
        • T
        • F
        • -
        • S
      • 09:25 JAX
        14:00 ORD
        5Hrs, 35m 1 Stop (IAD)
      • JAXJacksonville International Airport 09:25 - ORD 14:00 5h 35m 1 Stop (IAD) Washington
      • JAXJacksonville International Airport 09:25
        IADWashington Dulles International Airport 12:40
      • IADWashington Dulles International Airport 11:15
        ORDChicago O'Hare International Airport 14:00
      • 5h 35m (1h 25m)
      • 1 Stop IAD · Washington 1h 25m
      • United Airlines (UA 2477)Boeing 737 Max 8 Passenger
        United Airlines (UA 1581)Airbus
      • United Airlines (UA 2477)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 09:25 JAX
        14:05 ORD
        5Hrs, 40m 1 Stop (IAD)
      • JAXJacksonville International Airport 09:25 - ORD 14:05 5h 40m 1 Stop (IAD) Washington
      • JAXJacksonville International Airport 09:25
        IADWashington Dulles International Airport 12:45
      • IADWashington Dulles International Airport 11:15
        ORDChicago O'Hare International Airport 14:05
      • 5h 40m (1h 30m)
      • 1 Stop IAD · Washington 1h 30m
      • United Airlines (UA 2477)Boeing 737 Max 8 Passenger
        United Airlines (UA 1581)Airbus
      • United Airlines (UA 2477)
        • -
        • T
        • W
        • T
        • -
        • -
        • -
      • 09:25 JAX
        14:05 ORD
        5Hrs, 40m 1 Stop (IAD)
      • JAXJacksonville International Airport 09:25 - ORD 14:05 5h 40m 1 Stop (IAD) Washington
      • JAXJacksonville International Airport 09:25
        IADWashington Dulles International Airport 12:45
      • IADWashington Dulles International Airport 11:15
        ORDChicago O'Hare International Airport 14:05
      • 5h 40m (1h 30m)
      • 1 Stop IAD · Washington 1h 30m
      • United Airlines (UA 2477)Boeing 737 Max 8 Passenger
        United Airlines (UA 1581)Boeing 737 700
      • United Airlines (UA 2477)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • 09:25 JAX
        14:15 ORD
        5Hrs, 50m 1 Stop (IAD)
      • JAXJacksonville International Airport 09:25 - ORD 14:15 5h 50m 1 Stop (IAD) Washington
      • JAXJacksonville International Airport 09:25
        IADWashington Dulles International Airport 12:55
      • IADWashington Dulles International Airport 11:15
        ORDChicago O'Hare International Airport 14:15
      • 5h 50m (1h 40m)
      • 1 Stop IAD · Washington 1h 40m
      • United Airlines (UA 2477)Boeing 737 Max 8 Passenger
        United Airlines (UA 1581)Airbus
      • United Airlines (UA 2477)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 10:04 JAX
        15:51 ORD
        6Hrs, 47m 1 Stop (CLT)
      • JAXJacksonville International Airport 10:04 - ORD 15:51 6h 47m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 10:04
        CLTCharlotte Airport 14:41
      • CLTCharlotte Airport 11:30
        ORDChicago O'Hare International Airport 15:51
      • 6h 47m (3h 11m)
      • 1 Stop CLT · Charlotte 3h 11m
      • American Airlines (AA 1467)Airbus
        American Airlines (AA 614)Boeing 737 800
      • American Airlines (AA 1467)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 10:04 JAX
        14:12 ORD
        5Hrs, 08m 1 Stop (CLT)
      • JAXJacksonville International Airport 10:04 - ORD 14:12 5h 08m 1 Stop (CLT) Charlotte
      • JAXJacksonville International Airport 10:04
        CLTCharlotte Airport 13:04
      • CLTCharlotte Airport 11:30
        ORDChicago O'Hare International Airport 14:12
      • 5h 08m (1h 34m)
      • 1 Stop CLT · Charlotte 1h 34m
      • American Airlines (AA 1467)Airbus
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 1467)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 10:21 JAX
        15:08 ORD
        5Hrs, 47m 1 Stop (PHL)
      • JAXJacksonville International Airport 10:21 - ORD 15:08 5h 47m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 10:21
        PHLPhiladelphia International Airport 13:40
      • PHLPhiladelphia International Airport 12:25
        ORDChicago O'Hare International Airport 15:08
      • 5h 47m (1h 15m)
      • 1 Stop PHL · Philadelphia 1h 15m
      • American Airlines (AA 5458)Canadair Regional
        American Airlines (AA 470)Airbus
      • American Airlines (AA 5458)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 10:23 JAX
        15:16 ORD
        5Hrs, 53m 1 Stop (PHL)
      • JAXJacksonville International Airport 10:23 - ORD 15:16 5h 53m 1 Stop (PHL) Philadelphia
      • JAXJacksonville International Airport 10:23
        PHLPhiladelphia International Airport 13:48
      • PHLPhiladelphia International Airport 12:27
        ORDChicago O'Hare International Airport 15:16
      • 5h 53m (1h 21m)
      • 1 Stop PHL · Philadelphia 1h 21m
      • American Airlines (AA 5458)Canadair Regional
        American Airlines (AA 470)Airbus
      • American Airlines (AA 5458)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 10:45 JAX
        14:50 MDW
        5Hrs, 05m 1 Stop (BWI)
      • JAXJacksonville International Airport 10:45 - MDW 14:50 5h 05m 1 Stop (BWI) Baltimore
      • JAXJacksonville International Airport 10:45
        BWIBaltimore Washington International Airport 13:45
      • BWIBaltimore Washington International Airport 12:35
        MDWChicago Midway Airport 14:50
      • 5h 05m (1h 10m)
      • 1 Stop BWI · Baltimore 1h 10m
      • Southwest Airlines (WN 954)Boeing 737 700
        Southwest Airlines (WN 1689)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 954)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 11:05 JAX
        15:40 MDW
        5Hrs, 35m 1 Stop (STL)
      • JAXJacksonville International Airport 11:05 - MDW 15:40 5h 35m 1 Stop (STL) Saint Louis
      • JAXJacksonville International Airport 11:05
        STLSt Louis Lambert Intl Airport 14:30
      • STLSt Louis Lambert Intl Airport 12:20
        MDWChicago Midway Airport 15:40
      • 5h 35m (2h 10m)
      • 1 Stop STL · Saint Louis 2h 10m
      • Southwest Airlines (WN 2151)Boeing 737 700
        Southwest Airlines (WN 1253)Boeing 737 700
      • Southwest Airlines (WN 2151)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 11:05 JAX
        16:40 MDW
        6Hrs, 35m 1 Stop (BWI)
      • JAXJacksonville International Airport 11:05 - MDW 16:40 6h 35m 1 Stop (BWI) Baltimore
      • JAXJacksonville International Airport 11:05
        BWIBaltimore Washington International Airport 15:35
      • BWIBaltimore Washington International Airport 12:55
        MDWChicago Midway Airport 16:40
      • 6h 35m (2h 40m)
      • 1 Stop BWI · Baltimore 2h 40m
      • Southwest Airlines (WN 1475)Boeing 737 800
        Southwest Airlines (WN 4710)Boeing 737 800
      • Southwest Airlines (WN 1475)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:11 JAX
        16:16 ORD
        6Hrs, 05m 1 Stop (DCA)
      • JAXJacksonville International Airport 11:11 - ORD 16:16 6h 05m 1 Stop (DCA) Washington
      • JAXJacksonville International Airport 11:11
        DCAWashington Ronald Reagan National Airport 14:54
      • DCAWashington Ronald Reagan National Airport 13:05
        ORDChicago O'Hare International Airport 16:16
      • 6h 05m (1h 49m)
      • 1 Stop DCA · Washington 1h 49m
      • American Airlines (AA 1181)Airbus
        American Airlines (AA 1762)Boeing 737 800
      • American Airlines (AA 1181)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
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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 25 minutes. Check latest flight schedules & prices on Wego.

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

      The most popular airline flying from Jacksonville to Chicago is American Airlines. Find the latest flight deals 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 19:00. 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.

      All Airports in Jacksonville

      Jacksonville International Airport JAX

      Popular Airlines Flying From Jacksonville to Chicago

      American Airlines ‏()

      Popular Destinations From Chicago

      Popular Destinations From Jacksonville

      Popular Hotels in Chicago

      Hotels In Popular Destinations