Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Fort Myers to Chicago is Spirit Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Fort Myers to Chicago is May.
-
May 2024
-
Jun 2024
-
Jul 2024
-
Aug 2024
-
Sep 2024
-
Oct 2024
-
Nov 2024
-
Dec 2024
-
Jan 2025
-
Feb 2025
-
Mar 2025
-
Apr 2025
Cheapest Day of the Week
Tuesday
The cheapest day(s) of the week to fly from Fort Myers to Chicago is Tuesday.
-
Sun Sunday
-
Mon Monday
-
Tue Tuesday
-
Wed Wednesday
-
Thu Thursday
-
Fri Friday
-
Sat Saturday
Cheapest Time
7pm
The cheapest time of the day to fly from Fort Myers to Chicago is in the evening.
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
-
Depart
Earliest
- Earliest
- Latest
-
Arrive
- Earliest
- Latest
-
Airline
Filter by Airline
All
-
Total Duration
- Shortest
- Longest
-
Stopover
All
-
Availability
- M
- T
- W
- T
- F
- S
- S
-
20:40 - 22:40RSW - MDW
-
20:40 (RSW)Southwest Florida International Airport
-
22:40 (MDW)Chicago Midway Airport
-
(WN 3220)Boeing 737 700 - 3h
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
20:55 - 22:50RSW - MDW
-
20:55 (RSW)Southwest Florida International Airport
-
22:50 (MDW)Chicago Midway Airport
-
(WN 3220)Boeing 737 700 - 2h 55m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
06:50 - 08:40RSW - MDW
-
06:50 (RSW)Southwest Florida International Airport
-
08:40 (MDW)Chicago Midway Airport
-
(WN 3218)Boeing 737 Max 8 Passenger - 2h 50m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
07:15 - 09:05RSW - MDW
-
07:15 (RSW)Southwest Florida International Airport
-
09:05 (MDW)Chicago Midway Airport
-
(WN 3218)Boeing 737 Max 8 Passenger - 2h 50m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
07:35 - 09:25RSW - MDW
-
07:35 (RSW)Southwest Florida International Airport
-
09:25 (MDW)Chicago Midway Airport
-
(WN 3218)Boeing 737 Max 8 Passenger - 2h 50m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
-
07:35 - 09:20RSW - MDW
-
07:35 (RSW)Southwest Florida International Airport
-
09:20 (MDW)Chicago Midway Airport
-
(WN 3218)Boeing 737 800 - 2h 45m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
07:45 - 09:45RSW - ORD
-
07:45 (RSW)Southwest Florida International Airport
-
09:45 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2673)Boeing 737 800 - 3h
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
09:24 - 11:36RSW - ORD
-
09:24 (RSW)Southwest Florida International Airport
-
11:36 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1944)Boeing 737 800 - 3h 12m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
12:30 - 14:30RSW - ORD
-
12:30 (RSW)Southwest Florida International Airport
-
14:30 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 511)Boeing 737 800 - 3h
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
12:30 - 14:25RSW - MDW
-
12:30 (RSW)Southwest Florida International Airport
-
14:25 (MDW)Chicago Midway Airport
-
(WN 948)Boeing 737 800 - 2h 55m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
-
12:40 - 16:35RSW - MDW
-
12:40 (RSW)Southwest Florida International Airport
-
16:35 (MDW)Chicago Midway Airport
-
(WN 3408)Boeing 737 700 - 4h 55m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
12:40 - 14:40RSW - MDW
-
12:40 (RSW)Southwest Florida International Airport
-
14:40 (MDW)Chicago Midway Airport
-
(WN 948)Boeing 737 800 - 3h
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
14:30 - 16:45RSW - ORD
-
14:30 (RSW)Southwest Florida International Airport
-
16:45 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 785)Airbus A321 Neo - 3h 15m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus A321 Neo
-
14:45 - 16:40RSW - MDW
-
14:45 (RSW)Southwest Florida International Airport
-
16:40 (MDW)Chicago Midway Airport
-
(WN 948)Boeing 737 800 - 2h 55m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
-
15:31 - 17:45RSW - ORD
-
15:31 (RSW)Southwest Florida International Airport
-
17:45 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1929)Boeing 737 800 - 3h 14m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
16:30 - 18:30RSW - ORD
-
16:30 (RSW)Southwest Florida International Airport
-
18:30 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2305)Boeing 737 800 - 3h
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
17:30 - 19:25RSW - MDW
-
17:30 (RSW)Southwest Florida International Airport
-
19:25 (MDW)Chicago Midway Airport
-
(WN 3220)Boeing 737 Max 8 Passenger - 2h 55m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
18:10 - 20:05RSW - MDW
-
18:10 (RSW)Southwest Florida International Airport
-
20:05 (MDW)Chicago Midway Airport
-
(WN 3220)Boeing 737 800 - 2h 55m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
Connecting Flights
-
20:15 - 22:00RSW - STL22:50 - 23:55STL - MDW
-
20:15 (RSW)Southwest Florida International Airport22:50 (STL)St Louis Lambert Intl Airport
-
22:00 (STL)St Louis Lambert Intl Airport23:55 (MDW)Chicago Midway Airport
-
(WN 6028)Boeing 737 800 (WN 3244)Boeing 737 800 - 4h 40m (50m)
- STL Saint Louis 50m
-
- -
- -
- -
- -
- -
- -
- S
-
05:30 - 07:55RSW - BWI08:40 - 10:00BWI - ORD
-
05:30 (RSW)Southwest Florida International Airport08:40 (BWI)Baltimore Washington International Airport
-
07:55 (BWI)Baltimore Washington International Airport10:00 (ORD)Chicago O'Hare International Airport
-
(WN 1097)Boeing 737 800 (WN 3626)Boeing 737 800 - 5h 30m (45m)
- BWI Baltimore 45m
-
- M
- -
- -
- T
- F
- -
- -
-
06:00 - 07:50RSW - ATL09:50 - 10:45ATL - MDW
-
06:00 (RSW)Southwest Florida International Airport09:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
07:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport10:45 (MDW)Chicago Midway Airport
-
(WN 320)Boeing 737 700 (WN 5518)Boeing 737 Max 8 Passenger - 5h 45m (2h)
- ATL Atlanta 2h
-
- -
- -
- -
- -
- -
- -
- S
-
06:00 - 07:45RSW - ATL10:40 - 11:35ATL - MDW
-
06:00 (RSW)Southwest Florida International Airport10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
07:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:35 (MDW)Chicago Midway Airport
-
(WN 320)Boeing 737 Max 8 Passenger (WN 5518)Boeing 737 Max 8 Passenger - 6h 35m (2h 55m)
- ATL Atlanta 2h 55m
-
- -
- -
- -
- -
- -
- S
- -
-
06:10 - 07:55RSW - ATL10:45 - 11:40ATL - MDW
-
06:10 (RSW)Southwest Florida International Airport10:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
07:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:40 (MDW)Chicago Midway Airport
-
(WN 320)Boeing 737 700 (WN 5518)Boeing 737 Max 8 Passenger - 6h 30m (2h 50m)
- ATL Atlanta 2h 50m
-
- M
- -
- -
- T
- F
- -
- -
-
06:10 - 07:55RSW - ATL08:30 - 09:25ATL - MDW
-
06:10 (RSW)Southwest Florida International Airport08:30 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
07:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport09:25 (MDW)Chicago Midway Airport
-
(WN 320)Boeing 737 700 (WN 908)Boeing 737 700 - 4h 15m (35m)
- ATL Atlanta 35m
-
- M
- -
- -
- T
- F
- -
- -
-
08:15 - 09:50RSW - STL12:20 - 13:25STL - MDW
-
08:15 (RSW)Southwest Florida International Airport12:20 (STL)St Louis Lambert Intl Airport
-
09:50 (STL)St Louis Lambert Intl Airport13:25 (MDW)Chicago Midway Airport
-
(WN 2851)Boeing 737 700 (WN 1268)Boeing 737 700 - 6h 10m (2h 30m)
- STL Saint Louis 2h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
08:15 - 09:50RSW - STL12:35 - 13:40STL - MDW
-
08:15 (RSW)Southwest Florida International Airport12:35 (STL)St Louis Lambert Intl Airport
-
09:50 (STL)St Louis Lambert Intl Airport13:40 (MDW)Chicago Midway Airport
-
(WN 2851)Boeing 737 Max 8 Passenger (WN 3241)Boeing 737 700 - 6h 25m (2h 45m)
- STL Saint Louis 2h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
09:25 - 11:50RSW - CMH13:55 - 14:05CMH - MDW
-
09:25 (RSW)Southwest Florida International Airport13:55 (CMH)Columbus Port Columbus Intl Airport
-
11:50 (CMH)Columbus Port Columbus Intl Airport14:05 (MDW)Chicago Midway Airport
-
(WN 3915)Boeing 737 700 (WN 6025)Boeing 737 700 - 5h 40m (2h 05m)
- CMH Columbus 2h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
09:40 - 12:05RSW - BWI13:05 - 14:15BWI - ORD
-
09:40 (RSW)Southwest Florida International Airport13:05 (BWI)Baltimore Washington International Airport
-
12:05 (BWI)Baltimore Washington International Airport14:15 (ORD)Chicago O'Hare International Airport
-
(WN 1771)Boeing 737 800 (WN 3191)Boeing 737 700 - 5h 35m (1h)
- BWI Baltimore 1h
-
- -
- T
- W
- -
- -
- -
- -
-
09:40 - 12:05RSW - BWI13:05 - 14:05BWI - MDW
-
09:40 (RSW)Southwest Florida International Airport13:05 (BWI)Baltimore Washington International Airport
-
12:05 (BWI)Baltimore Washington International Airport14:05 (MDW)Chicago Midway Airport
-
(WN 1771)Boeing 737 800 (WN 5950)Boeing 737 800 - 5h 25m (1h)
- BWI Baltimore 1h
-
- -
- T
- W
- -
- -
- -
- -
-
09:55 - 12:25RSW - BWI13:45 - 14:45BWI - MDW
-
09:55 (RSW)Southwest Florida International Airport13:45 (BWI)Baltimore Washington International Airport
-
12:25 (BWI)Baltimore Washington International Airport14:45 (MDW)Chicago Midway Airport
-
(WN 1771)Boeing 737 800 (WN 5950)Boeing 737 800 - 5h 50m (1h 20m)
- BWI Baltimore 1h 20m
-
- M
- -
- -
- T
- F
- -
- -
-
10:15 - 11:20RSW - BNA12:55 - 14:30BNA - MDW
-
10:15 (RSW)Southwest Florida International Airport12:55 (BNA)Nashville Airport
-
11:20 (BNA)Nashville Airport14:30 (MDW)Chicago Midway Airport
-
(WN 679)Boeing 737 800 (WN 5597)Boeing 737 800 - 5h 15m (1h 35m)
- BNA Nashville 1h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
10:30 - 12:55RSW - BWI15:35 - 16:35BWI - MDW
-
10:30 (RSW)Southwest Florida International Airport15:35 (BWI)Baltimore Washington International Airport
-
12:55 (BWI)Baltimore Washington International Airport16:35 (MDW)Chicago Midway Airport
-
(WN 1771)Boeing 737 Max 8 Passenger (WN 2136)Boeing 737 Max 8 Passenger - 7h 05m (2h 40m)
- BWI Baltimore 2h 40m
-
- -
- -
- -
- -
- -
- -
- S
-
10:50 - 13:20RSW - BWI15:10 - 16:25BWI - ORD
-
10:50 (RSW)Southwest Florida International Airport15:10 (BWI)Baltimore Washington International Airport
-
13:20 (BWI)Baltimore Washington International Airport16:25 (ORD)Chicago O'Hare International Airport
-
(WN 1771)Boeing 737 700 (WN 3191)Boeing 737 700 - 6h 35m (1h 50m)
- BWI Baltimore 1h 50m
-
- -
- -
- -
- -
- -
- S
- -
-
10:50 - 13:20RSW - BWI16:00 - 17:00BWI - MDW
-
10:50 (RSW)Southwest Florida International Airport16:00 (BWI)Baltimore Washington International Airport
-
13:20 (BWI)Baltimore Washington International Airport17:00 (MDW)Chicago Midway Airport
-
(WN 1771)Boeing 737 700 (WN 2136)Boeing 737 800 - 7h 10m (2h 40m)
- BWI Baltimore 2h 40m
-
- -
- -
- -
- -
- -
- S
- -
-
10:55 - 13:30RSW - PIT16:00 - 16:25PIT - MDW
-
10:55 (RSW)Southwest Florida International Airport16:00 (PIT)Pittsburgh International Airport
-
13:30 (PIT)Pittsburgh International Airport16:25 (MDW)Chicago Midway Airport
-
(WN 3939)Boeing 737 700 (WN 3207)Boeing 737 700 - 6h 30m (2h 30m)
- PIT Pittsburgh 2h 30m
-
- -
- -
- -
- -
- -
- S
- -
-
11:35 - 13:00RSW - HOU14:15 - 16:40HOU - MDW
-
11:35 (RSW)Southwest Florida International Airport14:15 (HOU)Houston Hobby Airport
-
13:00 (HOU)Houston Hobby Airport16:40 (MDW)Chicago Midway Airport
-
(WN 1379)Boeing 737 700 (WN 3970)Boeing 737 700 - 6h 05m (1h 15m)
- HOU Houston 1h 15m
-
- -
- -
- -
- -
- -
- S
- -
-
13:10 - 15:35RSW - BWI16:40 - 17:40BWI - MDW
-
13:10 (RSW)Southwest Florida International Airport16:40 (BWI)Baltimore Washington International Airport
-
15:35 (BWI)Baltimore Washington International Airport17:40 (MDW)Chicago Midway Airport
-
(WN 1099)Boeing 737 700 (WN 2136)Boeing 737 Max 8 Passenger - 5h 30m (1h 05m)
- BWI Baltimore 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
13:20 - 15:05RSW - STL17:10 - 18:15STL - MDW
-
13:20 (RSW)Southwest Florida International Airport17:10 (STL)St Louis Lambert Intl Airport
-
15:05 (STL)St Louis Lambert Intl Airport18:15 (MDW)Chicago Midway Airport
-
(WN 3865)Boeing 737 700 (WN 3244)Boeing 737 800 - 5h 55m (2h 05m)
- STL Saint Louis 2h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
13:35 - 15:15RSW - STL18:25 - 19:30STL - MDW
-
13:35 (RSW)Southwest Florida International Airport18:25 (STL)St Louis Lambert Intl Airport
-
15:15 (STL)St Louis Lambert Intl Airport19:30 (MDW)Chicago Midway Airport
-
(WN 3865)Boeing 737 700 (WN 5687)Boeing 737 800 - 6h 55m (3h 10m)
- STL Saint Louis 3h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
13:45 - 16:15RSW - BWI18:45 - 19:45BWI - MDW
-
13:45 (RSW)Southwest Florida International Airport18:45 (BWI)Baltimore Washington International Airport
-
16:15 (BWI)Baltimore Washington International Airport19:45 (MDW)Chicago Midway Airport
-
(WN 5239)Boeing 737 700 (WN 1789)Boeing 737 Max 8 Passenger - 7h (2h 30m)
- BWI Baltimore 2h 30m
-
- -
- -
- -
- -
- -
- S
- -
-
14:25 - 16:05RSW - ATL17:05 - 18:00ATL - MDW
-
14:25 (RSW)Southwest Florida International Airport17:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
16:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport18:00 (MDW)Chicago Midway Airport
-
(WN 321)Boeing 737 700 (WN 5042)Boeing 737 Max 8 Passenger - 4h 35m (1h)
- ATL Atlanta 1h
-
- -
- -
- -
- -
- -
- S
- -
-
16:50 - 19:25RSW - BWI21:55 - 22:55BWI - MDW
-
16:50 (RSW)Southwest Florida International Airport21:55 (BWI)Baltimore Washington International Airport
-
19:25 (BWI)Baltimore Washington International Airport22:55 (MDW)Chicago Midway Airport
-
(WN 1100)Boeing 737 800 (WN 2775)Boeing 737 700 - 7h 05m (2h 30m)
- BWI Baltimore 2h 30m
-
- -
- -
- -
- -
- -
- -
- S
-
16:50 - 19:25RSW - BWI21:10 - 22:20BWI - ORD
-
16:50 (RSW)Southwest Florida International Airport21:10 (BWI)Baltimore Washington International Airport
-
19:25 (BWI)Baltimore Washington International Airport22:20 (ORD)Chicago O'Hare International Airport
-
(WN 1100)Boeing 737 800 (WN 5289)Boeing 737 800 - 6h 30m (1h 45m)
- BWI Baltimore 1h 45m
-
- -
- -
- -
- -
- -
- -
- S
-
17:10 - 19:00RSW - ATL20:35 - 21:30ATL - MDW
-
17:10 (RSW)Southwest Florida International Airport20:35 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
19:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport21:30 (MDW)Chicago Midway Airport
-
(WN 321)Boeing 737 800 (WN 5960)Boeing 737 800 - 5h 20m (1h 35m)
- ATL Atlanta 1h 35m
-
- M
- -
- -
- T
- F
- -
- -
-
18:50 - 20:30RSW - STL21:30 - 22:35STL - MDW
-
18:50 (RSW)Southwest Florida International Airport21:30 (STL)St Louis Lambert Intl Airport
-
20:30 (STL)St Louis Lambert Intl Airport22:35 (MDW)Chicago Midway Airport
-
(WN 6028)Boeing 737 Max 8 Passenger (WN 3244)Boeing 737 Max 8 Passenger - 4h 45m (1h)
- STL Saint Louis 1h
-
- -
- T
- W
- -
- -
- -
- -
No Schedules
Sorry, there are no schedules matching your filters. Try removing one.
reset
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 45 minutes. Check latest flight schedules & prices 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 05:30. The last flight of the day departs at 20:15. See the full list of flight times on Wego.
How many airlines offer direct flights from Fort Myers to Chicago?
There are 3 airlines that offer direct flights from Fort Myers to Chicago. Find out the list of airlines on Wego.
All Airports in Chicago
Popular destinations from Chicago
Popular destinations from Fort Myers
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel, Central Loop, Chicago
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel