Flight Routes from Chicago to Fort Myers

Trip type

Our cheapest offers for flights from Chicago to Fort Myers

Here you can compare cheap flights from Chicago (CHI) to Fort Myers (RSW) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Fort Myers. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
Fort Myers
Outbound
07/26/26
1 Stopover (MSP)
SY0262, SY0383
14h 36min
Return
08/05/26
1 Stopover (HVN)
XP0354, XP0421
23h 13min
Sun Country Airlines
$348
Best option
Chicago
Fort Myers
Outbound
06/25/26
direct
UA2618
03h 08min
Return
06/30/26
direct
AA2433
03h 19min
United Airlines ?
$354
Chicago
Fort Myers
Outbound
07/26/26
direct
AA2433
02h 53min
Return
08/05/26
direct
AA2437
03h 17min
American Airlines ?
$381
Chicago
Fort Myers
Outbound
06/25/26
direct
UA2618
03h 08min
Return
06/30/26
direct
UA2738
03h 21min
United Airlines
$389
Chicago
Fort Myers
Outbound
06/25/26
direct
AA2437
02h 56min
Return
06/30/26
direct
AA2437
03h 29min
American Airlines ?
$523
Chicago
Fort Myers
Outbound
06/25/26
1 Stopover (MSP)
SY0262, SY0383
13h 01min
Return
06/30/26
2 Stopovers (CLE, ATL)
F92715, F94209, F91441
25h 50min
Sun Country Airlines ?
$563
Chicago
Fort Myers
Outbound
07/26/26
1 Stopover (BOS)
B60312, B62065
07h 23min
Return
08/05/26
1 Stopover (BOS)
B60266, B60811
08h 55min
JetBlue Airways ?
$601
Chicago
Fort Myers
Outbound
07/26/26
1 Stopover (MSP)
SY0262, SY0383
14h 36min
Return
08/05/26
3 Stopovers (MSP, DEN, MSP)
SY0384, SY0657, SY0652, SY0261
32h 53min
Sun Country Airlines ?
$615
Chicago
Fort Myers
Outbound
07/26/26
direct
UA2618
03h 08min
Return
08/05/26
direct
UA2494
03h 23min
United Airlines ?
$2,384
Chicago
Fort Myers
Outbound
06/25/26
1 Stopover (ATL)
DL2894, DL1736
07h 02min
Return
06/30/26
1 Stopover (MSP)
DL2219, DL1567
05h 58min
Delta Air Lines ?
$3,055
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to Fort Myers

Favorite airline: Spirit Airlines
The favorite airline for flights from Chicago to Fort Myers is Spirit Airlines.
Spirit Airlines
54 %
United Airlines
23 %
Sun Country Airlines
12 %
Direct flights are the cheapest connection
Direct flights on this route are $129.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
2 stops
03h 01min
13h 37min
23h 58min
102 USD
231 USD
2.052 USD
The favorite connection is non-stop
70 % of travelers decide to book a direct flight on this route.
Route
bookings
Direct flights
03h 01min, from 102 USD
70 %
1 stopover Minneapolis - St. Paul International Airport, MN
13h 37min, from 231 USD
18 %
1 stopover Hartsfield-Jackson Atlanta International Airport, GA
11h 45min, from 275 USD
6 %

Important flight information

Flight information: Chicago - Fort Myers

Roundtrip from 347,34 USD
Flight duration min. 02:45 / max. 03:50
Return flight duration min. 02:55/ max. 05:50
Distance 1791 km
Flights per week 128
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport Fort Myers-Southwest Florida Reg-FL (RSW)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Fort Myers
Flight destinations with a similar price
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