Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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      • Availability
        • M
        • T
        • W
        • T
        • F
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        • S
      • 19:30 RSW
        21:25 MDW
        2Hrs, 55m Direct
      • RSWSouthwest Florida International Airport 19:30 - MDW 21:25 2h 55m Direct
      • RSWSouthwest Florida International Airport 19:30
      • MDWChicago Midway Airport 21:25
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 4631)Boeing 737 700
      • Southwest Airlines (WN 4631)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 21:15 RSW
        23:10 MDW
        2Hrs, 55m Direct
      • RSWSouthwest Florida International Airport 21:15 - MDW 23:10 2h 55m Direct
      • RSWSouthwest Florida International Airport 21:15
      • MDWChicago Midway Airport 23:10
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 4631)Boeing 737 700
      • Southwest Airlines (WN 4631)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 700
      • 06:00 RSW
        08:00 MDW
        3Hrs, 00m Direct
      • RSWSouthwest Florida International Airport 06:00 - MDW 08:00 3h Direct
      • RSWSouthwest Florida International Airport 06:00
      • MDWChicago Midway Airport 08:00
      • 3h
      • Direct
      • Southwest Airlines (WN 1153)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1153)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 06:50 RSW
        08:45 MDW
        2Hrs, 55m Direct
      • RSWSouthwest Florida International Airport 06:50 - MDW 08:45 2h 55m Direct
      • RSWSouthwest Florida International Airport 06:50
      • MDWChicago Midway Airport 08:45
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 4965)Boeing 737 700
      • Southwest Airlines (WN 4965)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 07:15 RSW
        09:10 MDW
        2Hrs, 55m Direct
      • RSWSouthwest Florida International Airport 07:15 - MDW 09:10 2h 55m Direct
      • RSWSouthwest Florida International Airport 07:15
      • MDWChicago Midway Airport 09:10
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 1153)Boeing 737 800
      • Southwest Airlines (WN 1153)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 07:35 RSW
        09:43 ORD
        3Hrs, 08m Direct
      • RSWSouthwest Florida International Airport 07:35 - ORD 09:43 3h 08m Direct
      • RSWSouthwest Florida International Airport 07:35
      • ORDChicago O'Hare International Airport 09:43
      • 3h 08m
      • Direct
      • United Airlines (UA 2624)Boeing 737 900
      • United Airlines (UA 2624)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 900
      • 09:08 RSW
        11:16 ORD
        3Hrs, 08m Direct
      • RSWSouthwest Florida International Airport 09:08 - ORD 11:16 3h 08m Direct
      • RSWSouthwest Florida International Airport 09:08
      • ORDChicago O'Hare International Airport 11:16
      • 3h 08m
      • Direct
      • United Airlines (UA 2624)Boeing 737 900
      • United Airlines (UA 2624)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 900
      • 09:26 RSW
        11:34 ORD
        3Hrs, 08m Direct
      • RSWSouthwest Florida International Airport 09:26 - ORD 11:34 3h 08m Direct
      • RSWSouthwest Florida International Airport 09:26
      • ORDChicago O'Hare International Airport 11:34
      • 3h 08m
      • Direct
      • United Airlines (UA 2624)Boeing 737 900
      • United Airlines (UA 2624)
        • M
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        • T
        • -
        • S
        • -
      • Boeing 737 900
      • 09:45 RSW
        11:42 ORD
        2Hrs, 57m Direct
      • RSWSouthwest Florida International Airport 09:45 - ORD 11:42 2h 57m Direct
      • RSWSouthwest Florida International Airport 09:45
      • ORDChicago O'Hare International Airport 11:42
      • 2h 57m
      • Direct
      • Spirit Airlines (NK 488)Airbus Industrie A320 Sharklets
      • Spirit Airlines (NK 488)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus Industrie A320 Sharklets
      • 10:10 RSW
        12:05 MDW
        2Hrs, 55m Direct
      • RSWSouthwest Florida International Airport 10:10 - MDW 12:05 2h 55m Direct
      • RSWSouthwest Florida International Airport 10:10
      • MDWChicago Midway Airport 12:05
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 3212)Boeing 737 700
      • Southwest Airlines (WN 3212)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 11:00 RSW
        14:15 MDW
        4Hrs, 15m Direct
      • RSWSouthwest Florida International Airport 11:00 - MDW 14:15 4h 15m Direct
      • RSWSouthwest Florida International Airport 11:00
      • MDWChicago Midway Airport 14:15
      • 4h 15m
      • Direct
      • Southwest Airlines (WN 2328)Boeing 737 700
      • Southwest Airlines (WN 2328)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 12:40 RSW
        14:51 ORD
        3Hrs, 11m Direct
      • RSWSouthwest Florida International Airport 12:40 - ORD 14:51 3h 11m Direct
      • RSWSouthwest Florida International Airport 12:40
      • ORDChicago O'Hare International Airport 14:51
      • 3h 11m
      • Direct
      • United Airlines (UA 2856)Boeing 737 900
      • United Airlines (UA 2856)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Boeing 737 900
      • 12:40 RSW
        14:51 ORD
        3Hrs, 11m Direct
      • RSWSouthwest Florida International Airport 12:40 - ORD 14:51 3h 11m Direct
      • RSWSouthwest Florida International Airport 12:40
      • ORDChicago O'Hare International Airport 14:51
      • 3h 11m
      • Direct
      • United Airlines (UA 2856)Boeing 737 800
      • United Airlines (UA 2856)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 12:42 RSW
        14:41 ORD
        2Hrs, 59m Direct
      • RSWSouthwest Florida International Airport 12:42 - ORD 14:41 2h 59m Direct
      • RSWSouthwest Florida International Airport 12:42
      • ORDChicago O'Hare International Airport 14:41
      • 2h 59m
      • Direct
      • Spirit Airlines (NK 488)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 488)
        • -
        • -
        • -
        • T
        • -
        • S
        • S
      • Airbus Industrie A321 Sharklets
      • 12:45 RSW
        14:59 ORD
        3Hrs, 14m Direct
      • RSWSouthwest Florida International Airport 12:45 - ORD 14:59 3h 14m Direct
      • RSWSouthwest Florida International Airport 12:45
      • ORDChicago O'Hare International Airport 14:59
      • 3h 14m
      • Direct
      • American Airlines (AA 1929)Boeing 737 800
      • American Airlines (AA 1929)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • Boeing 737 800
      • 13:15 RSW
        15:15 MDW
        3Hrs, 00m Direct
      • RSWSouthwest Florida International Airport 13:15 - MDW 15:15 3h Direct
      • RSWSouthwest Florida International Airport 13:15
      • MDWChicago Midway Airport 15:15
      • 3h
      • Direct
      • Southwest Airlines (WN 3212)Boeing 737 800
      • Southwest Airlines (WN 3212)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 13:40 RSW
        15:40 MDW
        3Hrs, 00m Direct
      • RSWSouthwest Florida International Airport 13:40 - MDW 15:40 3h Direct
      • RSWSouthwest Florida International Airport 13:40
      • MDWChicago Midway Airport 15:40
      • 3h
      • Direct
      • Southwest Airlines (WN 4508)Boeing 737 800
      • Southwest Airlines (WN 4508)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 14:00 RSW
        16:14 ORD
        3Hrs, 14m Direct
      • RSWSouthwest Florida International Airport 14:00 - ORD 16:14 3h 14m Direct
      • RSWSouthwest Florida International Airport 14:00
      • ORDChicago O'Hare International Airport 16:14
      • 3h 14m
      • Direct
      • American Airlines (AA 1929)Boeing 737 800
      • American Airlines (AA 1929)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 800
      • 14:00 RSW
        16:15 ORD
        3Hrs, 15m Direct
      • RSWSouthwest Florida International Airport 14:00 - ORD 16:15 3h 15m Direct
      • RSWSouthwest Florida International Airport 14:00
      • ORDChicago O'Hare International Airport 16:15
      • 3h 15m
      • Direct
      • American Airlines (AA 1929)Boeing 737 800
      • American Airlines (AA 1929)
        • -
        • T
        • W
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 14:29 RSW
        16:41 ORD
        3Hrs, 12m Direct
      • RSWSouthwest Florida International Airport 14:29 - ORD 16:41 3h 12m Direct
      • RSWSouthwest Florida International Airport 14:29
      • ORDChicago O'Hare International Airport 16:41
      • 3h 12m
      • Direct
      • United Airlines (UA 2605)Airbus A321 Neo
      • United Airlines (UA 2605)
        • M
        • -
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        • T
        • F
        • -
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      • Airbus A321 Neo
      • 14:29 RSW
        16:41 ORD
        3Hrs, 12m Direct
      • RSWSouthwest Florida International Airport 14:29 - ORD 16:41 3h 12m Direct
      • RSWSouthwest Florida International Airport 14:29
      • ORDChicago O'Hare International Airport 16:41
      • 3h 12m
      • Direct
      • United Airlines (UA 2605)Boeing 737 900
      • United Airlines (UA 2605)
        • -
        • T
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 900
      • 15:12 RSW
        17:25 ORD
        3Hrs, 13m Direct
      • RSWSouthwest Florida International Airport 15:12 - ORD 17:25 3h 13m Direct
      • RSWSouthwest Florida International Airport 15:12
      • ORDChicago O'Hare International Airport 17:25
      • 3h 13m
      • Direct
      • American Airlines (AA 1929)Boeing 737 800
      • American Airlines (AA 1929)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 15:55 RSW
        22:51 ORD
        7Hrs, 56m Direct
      • RSWSouthwest Florida International Airport 15:55 - ORD 22:51 7h 56m Direct
      • RSWSouthwest Florida International Airport 15:55
      • ORDChicago O'Hare International Airport 22:51
      • 7h 56m
      • Direct
      • United Airlines (UA 2258)Boeing 737 900
      • United Airlines (UA 2258)
        • M
        • -
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 900
      • 16:25 RSW
        18:35 ORD
        3Hrs, 10m Direct
      • RSWSouthwest Florida International Airport 16:25 - ORD 18:35 3h 10m Direct
      • RSWSouthwest Florida International Airport 16:25
      • ORDChicago O'Hare International Airport 18:35
      • 3h 10m
      • Direct
      • United Airlines (UA 2289)Boeing 737 800
      • United Airlines (UA 2289)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 16:25 RSW
        18:35 ORD
        3Hrs, 10m Direct
      • RSWSouthwest Florida International Airport 16:25 - ORD 18:35 3h 10m Direct
      • RSWSouthwest Florida International Airport 16:25
      • ORDChicago O'Hare International Airport 18:35
      • 3h 10m
      • Direct
      • United Airlines (UA 2289)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2289)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 17:00 RSW
        18:55 MDW
        2Hrs, 55m Direct
      • RSWSouthwest Florida International Airport 17:00 - MDW 18:55 2h 55m Direct
      • RSWSouthwest Florida International Airport 17:00
      • MDWChicago Midway Airport 18:55
      • 2h 55m
      • Direct
      • Southwest Airlines (WN 2135)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2135)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 17:24 RSW
        19:38 ORD
        3Hrs, 14m Direct
      • RSWSouthwest Florida International Airport 17:24 - ORD 19:38 3h 14m Direct
      • RSWSouthwest Florida International Airport 17:24
      • ORDChicago O'Hare International Airport 19:38
      • 3h 14m
      • Direct
      • American Airlines (AA 1504)Boeing 737 800
      • American Airlines (AA 1504)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 800
      • 17:24 RSW
        19:39 ORD
        3Hrs, 15m Direct
      • RSWSouthwest Florida International Airport 17:24 - ORD 19:39 3h 15m Direct
      • RSWSouthwest Florida International Airport 17:24
      • ORDChicago O'Hare International Airport 19:39
      • 3h 15m
      • Direct
      • American Airlines (AA 1504)Boeing 737 800
      • American Airlines (AA 1504)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 17:25 RSW
        19:40 ORD
        3Hrs, 15m Direct
      • RSWSouthwest Florida International Airport 17:25 - ORD 19:40 3h 15m Direct
      • RSWSouthwest Florida International Airport 17:25
      • ORDChicago O'Hare International Airport 19:40
      • 3h 15m
      • Direct
      • American Airlines (AA 1504)Boeing 737 800
      • American Airlines (AA 1504)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 17:31 RSW
        19:45 ORD
        3Hrs, 14m Direct
      • RSWSouthwest Florida International Airport 17:31 - ORD 19:45 3h 14m Direct
      • RSWSouthwest Florida International Airport 17:31
      • ORDChicago O'Hare International Airport 19:45
      • 3h 14m
      • Direct
      • American Airlines (AA 1504)Boeing 737 800
      • American Airlines (AA 1504)
        • -
        • -
        • -
        • T
        • -
        • -
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      • Boeing 737 800
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      What’s the fastest flight time from Fort Myers to Chicago?

      The fastest flight time for direct flights from Fort Myers to Chicago is 2 hours 55 minutes. Check latest flight schedules & prices on Wego.

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

      The most popular airline flying from Fort Myers to Chicago is American Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Fort Myers?

      The flight distance between Fort Myers and Chicago is 1774km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 06:00. The last flight of the day departs at 19:30. See the full list of flight times on Wego.

      How many airlines offer direct flights from Fort Myers to Chicago?

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

      All Airports in Fort Myers

      Southwest Florida International Airport RSW

      Page Field FMY

      Popular Airlines flying from Fort Myers to Chicago

      American Airlines ‏()

      Popular Destinations from Chicago

      Popular Destinations from Fort Myers

      Popular Hotels in Chicago

      Hotels In Popular Destinations