Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Chicago to Fort Myers is United Airlines.
Cheapest Month
January
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Chicago to Fort Myers is January.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
Cheapest Day of the Week
Wednesday
The cheapest day(s) of the week to fly from Chicago to Fort Myers is Wednesday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Cheapest Time
11am
The cheapest time of the day to fly from Chicago to Fort Myers is in the morning.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Earliest
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Arrive
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Total Duration
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Stopover
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Availability
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20:10 - 23:55MDW - RSW
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20:10 (MDW)Chicago Midway Airport
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23:55 (RSW)Southwest Florida International Airport
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(WN 5357)Boeing 737 Max 8 Passenger - 2h 45m
- Direct
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- Boeing 737 Max 8 Passenger
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06:00 - 14:01ORD - RSW
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06:00 (ORD)Chicago O'Hare International Airport
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14:01 (RSW)Southwest Florida International Airport
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United Airlines (UA 1658)Boeing 737 800 - 7h 01m
- Direct
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- M
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- S
- Boeing 737 800
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06:30 - 10:10MDW - RSW
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06:30 (MDW)Chicago Midway Airport
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10:10 (RSW)Southwest Florida International Airport
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(WN 5357)Boeing 737 700 - 2h 40m
- Direct
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- Boeing 737 700
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07:25 - 11:05MDW - RSW
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07:25 (MDW)Chicago Midway Airport
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11:05 (RSW)Southwest Florida International Airport
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(WN 4910)Boeing 737 700 - 2h 40m
- Direct
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- Boeing 737 700
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07:30 - 11:30ORD - RSW
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07:30 (ORD)Chicago O'Hare International Airport
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11:30 (RSW)Southwest Florida International Airport
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United Airlines (UA 1740)Boeing 737 800 - 3h
- Direct
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- M
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- S
- Boeing 737 800
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07:50 - 11:30MDW - RSW
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07:50 (MDW)Chicago Midway Airport
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11:30 (RSW)Southwest Florida International Airport
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(WN 4910)Boeing 737 700 - 2h 40m
- Direct
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- M
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- Boeing 737 700
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09:04 - 19:15ORD - RSW
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09:04 (ORD)Chicago O'Hare International Airport
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19:15 (RSW)Southwest Florida International Airport
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United Airlines (UA 2033)Boeing 737 800 - 9h 11m
- Direct
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- S
- Boeing 737 800
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09:15 - 13:17ORD - RSW
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09:15 (ORD)Chicago O'Hare International Airport
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13:17 (RSW)Southwest Florida International Airport
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United Airlines (UA 1349)Airbus A321 Neo - 3h 02m
- Direct
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- Airbus A321 Neo
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09:20 - 13:00MDW - RSW
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09:20 (MDW)Chicago Midway Airport
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13:00 (RSW)Southwest Florida International Airport
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(WN 4910)Boeing 737 700 - 2h 40m
- Direct
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- S
- Boeing 737 700
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09:55 - 13:46ORD - RSW
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09:55 (ORD)Chicago O'Hare International Airport
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13:46 (RSW)Southwest Florida International Airport
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American Airlines (AA 1929)Boeing 737 800 - 2h 51m
- Direct
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- M
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- S
- Boeing 737 800
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11:05 - 15:05ORD - RSW
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11:05 (ORD)Chicago O'Hare International Airport
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15:05 (RSW)Southwest Florida International Airport
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United Airlines (UA 2389)Boeing 737 800 - 3h
- Direct
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- M
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- S
- Boeing 737 800
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11:40 - 15:20MDW - RSW
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11:40 (MDW)Chicago Midway Airport
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15:20 (RSW)Southwest Florida International Airport
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(WN 4910)Boeing 737 700 - 2h 40m
- Direct
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- Boeing 737 700
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13:00 - 16:45MDW - RSW
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13:00 (MDW)Chicago Midway Airport
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16:45 (RSW)Southwest Florida International Airport
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(WN 3063)Boeing 737 Max 8 Passenger - 2h 45m
- Direct
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- Boeing 737 Max 8 Passenger
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13:15 - 17:00MDW - RSW
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13:15 (MDW)Chicago Midway Airport
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17:00 (RSW)Southwest Florida International Airport
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(WN 3063)Boeing 737 700 - 2h 45m
- Direct
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- M
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- F
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- Boeing 737 700
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14:00 - 18:00ORD - RSW
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14:00 (ORD)Chicago O'Hare International Airport
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18:00 (RSW)Southwest Florida International Airport
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United Airlines (UA 1092)Boeing 737 800 - 3h
- Direct
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- S
- Boeing 737 800
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15:05 - 18:55MDW - RSW
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15:05 (MDW)Chicago Midway Airport
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18:55 (RSW)Southwest Florida International Airport
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(WN 799)Boeing 737 800 - 2h 50m
- Direct
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- Boeing 737 800
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17:25 - 21:10MDW - RSW
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17:25 (MDW)Chicago Midway Airport
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21:10 (RSW)Southwest Florida International Airport
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(WN 5357)Boeing 737 Max 8 Passenger - 2h 45m
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- Boeing 737 Max 8 Passenger
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18:15 - 22:15ORD - RSW
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18:15 (ORD)Chicago O'Hare International Airport
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22:15 (RSW)Southwest Florida International Airport
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United Airlines (UA 1732)Boeing 737 800 - 3h
- Direct
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- Boeing 737 800
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18:35 - 22:25MDW - RSW
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18:35 (MDW)Chicago Midway Airport
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22:25 (RSW)Southwest Florida International Airport
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(WN 5357)Boeing 737 700 - 2h 50m
- Direct
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- Boeing 737 700
Connecting Flights
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06:05 - 08:55MDW - ATL10:55 - 12:30ATL - RSW
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06:05 (MDW)Chicago Midway Airport10:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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08:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport12:30 (RSW)Southwest Florida International Airport
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(WN 925)Boeing 737 800 (WN 4049)Boeing 737 Max 8 Passenger - 5h 25m (2h)
- ATL Atlanta 2h
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06:05 - 08:55MDW - ATL10:30 - 12:05ATL - RSW
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06:05 (MDW)Chicago Midway Airport10:30 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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08:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport12:05 (RSW)Southwest Florida International Airport
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(WN 925)Boeing 737 700 (WN 4049)Boeing 737 700 - 5h (1h 35m)
- ATL Atlanta 1h 35m
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07:05 - 09:25MDW - DAL10:10 - 13:45DAL - RSW
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07:05 (MDW)Chicago Midway Airport10:10 (DAL)Dallas/Fort Worth Love Field Airport
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09:25 (DAL)Dallas/Fort Worth Love Field Airport13:45 (RSW)Southwest Florida International Airport
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(WN 1102)Boeing 737 800 (WN 5073)Boeing 737 700 - 5h 40m (45m)
- DAL Dallas 45m
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09:35 - 12:00MDW - BUF13:45 - 16:45BUF - RSW
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09:35 (MDW)Chicago Midway Airport13:45 (BUF)Buffalo Airport
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12:00 (BUF)Buffalo Airport16:45 (RSW)Southwest Florida International Airport
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(WN 162)Boeing 737 Max 8 Passenger (WN 3563)Boeing 737 800 - 6h 10m (1h 45m)
- BUF Buffalo 1h 45m
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10:05 - 11:15MDW - STL14:15 - 17:40STL - RSW
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10:05 (MDW)Chicago Midway Airport14:15 (STL)St Louis Lambert Intl Airport
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11:15 (STL)St Louis Lambert Intl Airport17:40 (RSW)Southwest Florida International Airport
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(WN 3487)Boeing 737 800 (WN 3572)Boeing 737 700 - 6h 35m (3h)
- STL Saint Louis 3h
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10:05 - 11:30MDW - BNA14:05 - 17:05BNA - RSW
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10:05 (MDW)Chicago Midway Airport14:05 (BNA)Nashville Airport
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11:30 (BNA)Nashville Airport17:05 (RSW)Southwest Florida International Airport
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(WN 433)Boeing 737 800 (WN 4841)Boeing 737 700 - 6h (2h 35m)
- BNA Nashville 2h 35m
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10:35 - 13:20MDW - BWI15:20 - 18:00BWI - RSW
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10:35 (MDW)Chicago Midway Airport15:20 (BWI)Baltimore Washington International Airport
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13:20 (BWI)Baltimore Washington International Airport18:00 (RSW)Southwest Florida International Airport
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(WN 575)Boeing 737 Max 8 Passenger (WN 2529)Boeing 737 Max 8 Passenger - 6h 25m (2h)
- BWI Baltimore 2h
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11:10 - 13:20MDW - CMH15:50 - 18:15CMH - RSW
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11:10 (MDW)Chicago Midway Airport15:50 (CMH)Columbus Port Columbus Intl Airport
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13:20 (CMH)Columbus Port Columbus Intl Airport18:15 (RSW)Southwest Florida International Airport
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(WN 1223)Boeing 737 700 (WN 1749)Boeing 737 700 - 6h 05m (2h 30m)
- CMH Columbus 2h 30m
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11:25 - 14:15ORD - BWI15:35 - 18:15BWI - RSW
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11:25 (ORD)Chicago O'Hare International Airport15:35 (BWI)Baltimore Washington International Airport
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14:15 (BWI)Baltimore Washington International Airport18:15 (RSW)Southwest Florida International Airport
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(WN 5932)Boeing 737 700 (WN 2529)Boeing 737 Max 8 Passenger - 5h 50m (1h 20m)
- BWI Baltimore 1h 20m
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12:45 - 15:10MDW - BUF16:15 - 19:10BUF - RSW
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12:45 (MDW)Chicago Midway Airport16:15 (BUF)Buffalo Airport
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15:10 (BUF)Buffalo Airport19:10 (RSW)Southwest Florida International Airport
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(WN 2086)Boeing 737 800 (WN 5607)Boeing 737 700 - 5h 25m (1h 05m)
- BUF Buffalo 1h 05m
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12:50 - 15:40MDW - BWI16:50 - 19:30BWI - RSW
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12:50 (MDW)Chicago Midway Airport16:50 (BWI)Baltimore Washington International Airport
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15:40 (BWI)Baltimore Washington International Airport19:30 (RSW)Southwest Florida International Airport
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(WN 1015)Boeing 737 800 (WN 2529)Boeing 737 800 - 5h 40m (1h 10m)
- BWI Baltimore 1h 10m
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- S
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12:55 - 15:45MDW - ATL18:25 - 20:00ATL - RSW
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12:55 (MDW)Chicago Midway Airport18:25 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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15:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport20:00 (RSW)Southwest Florida International Airport
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(WN 576)Boeing 737 700 (WN 4050)Boeing 737 700 - 6h 05m (2h 40m)
- ATL Atlanta 2h 40m
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13:30 - 15:05ORD - BNA18:30 - 21:35BNA - RSW
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13:30 (ORD)Chicago O'Hare International Airport18:30 (BNA)Nashville Airport
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15:05 (BNA)Nashville Airport21:35 (RSW)Southwest Florida International Airport
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(WN 4855)Boeing 737 800 (WN 4841)Boeing 737 700 - 7h 05m (3h 25m)
- BNA Nashville 3h 25m
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13:55 - 15:05MDW - STL17:20 - 20:50STL - RSW
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13:55 (MDW)Chicago Midway Airport17:20 (STL)St Louis Lambert Intl Airport
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15:05 (STL)St Louis Lambert Intl Airport20:50 (RSW)Southwest Florida International Airport
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(WN 5388)Boeing 737 700 (WN 4956)Boeing 737 800 - 5h 55m (2h 15m)
- STL Saint Louis 2h 15m
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- S
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14:25 - 16:45MDW - PIT17:45 - 20:15PIT - RSW
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14:25 (MDW)Chicago Midway Airport17:45 (PIT)Pittsburgh International Airport
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16:45 (PIT)Pittsburgh International Airport20:15 (RSW)Southwest Florida International Airport
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(WN 2551)Boeing 737 700 (WN 4063)Boeing 737 700 - 4h 50m (1h)
- PIT 1h
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- M
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15:00 - 16:25MDW - BNA18:30 - 21:35BNA - RSW
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15:00 (MDW)Chicago Midway Airport18:30 (BNA)Nashville Airport
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16:25 (BNA)Nashville Airport21:35 (RSW)Southwest Florida International Airport
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(WN 3207)Boeing 737 700 (WN 4841)Boeing 737 700 - 5h 35m (2h 05m)
- BNA Nashville 2h 05m
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15:35 - 18:25MDW - ATL21:50 - 23:30ATL - RSW
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15:35 (MDW)Chicago Midway Airport21:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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18:25 (ATL)Atlanta Hartsfield-Jackson Intl Airport23:30 (RSW)Southwest Florida International Airport
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(WN 1476)Boeing 737 Max 8 Passenger (WN 4050)Boeing 737 800 - 6h 55m (3h 25m)
- ATL Atlanta 3h 25m
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- M
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- F
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16:30 - 19:15MDW - BWI20:00 - 22:35BWI - RSW
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16:30 (MDW)Chicago Midway Airport20:00 (BWI)Baltimore Washington International Airport
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19:15 (BWI)Baltimore Washington International Airport22:35 (RSW)Southwest Florida International Airport
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(WN 1833)Boeing 737 Max 8 Passenger (WN 2625)Boeing 737 800 - 5h 05m (45m)
- BWI Baltimore 45m
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- M
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- F
- -
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16:40 - 17:50+ 1MDW - STL20:40 - 00:05+ 1STL - RSW
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16:40 (MDW)Chicago Midway Airport20:40 (STL)St Louis Lambert Intl Airport
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17:50 (STL)St Louis Lambert Intl Airport + 100:05 (RSW)Southwest Florida International Airport
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(WN 5388)Boeing 737 700 (WN 4956)Boeing 737 700 - 6h 25m (2h 50m)
- STL Saint Louis 2h 50m
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- S
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17:05 - 19:55MDW - ATL21:40 - 23:15ATL - RSW
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17:05 (MDW)Chicago Midway Airport21:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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19:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport23:15 (RSW)Southwest Florida International Airport
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(WN 1476)Boeing 737 800 (WN 4050)Boeing 737 800 - 5h 10m (1h 45m)
- ATL Atlanta 1h 45m
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- T
- W
- -
- -
- -
- -
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18:25 - 19:50MDW - BNA20:45 - 23:45BNA - RSW
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18:25 (MDW)Chicago Midway Airport20:45 (BNA)Nashville Airport
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19:50 (BNA)Nashville Airport23:45 (RSW)Southwest Florida International Airport
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(WN 3207)Boeing 737 700 (WN 4841)Boeing 737 700 - 4h 20m (55m)
- BNA Nashville 55m
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- M
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- T
- F
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No Schedules
Sorry, there are no schedules matching your filters. Try removing one.
reset
What’s the fastest flight time from Chicago to Fort Myers?
The fastest flight time for direct flights from Chicago to Fort Myers is 2 hours 40 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Chicago to Fort Myers?
The most popular airline flying from Chicago to Fort Myers is American Airlines. Find the latest flight deals on Wego.
How far is Fort Myers from Chicago?
The flight distance between Chicago and Fort Myers 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 20:10. See the full list of flight times on Wego.
How many airlines offer direct flights from Chicago to Fort Myers?
There are 3 airlines that offer direct flights from Chicago to Fort Myers. Find out the list of airlines on Wego.
All Airports in Chicago
Popular Airlines flying from Chicago to Fort Myers
Popular destinations from Fort Myers
Popular destinations from Chicago
Popular Hotels in Fort Myers
- Comfort Inn & Suites Airport
- Home2 Suites by Hilton Fort Myers Colonial Blvd
- Hilton Garden Inn Ft Myers
- Drury Inn & Suites Fort Myers Airport FGCU
- Doubletree by Hilton Fort Myers at Bell Tower Shops
- Allure Suites
- Luminary Hotel & Co., Autograph Collection
- Best Western Fort Myers Inn & Suites
- Marriott Sanibel Harbour Resort & Spa
- Hyatt Place Fort Myers/at The Forum