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Cheap flights Chicago to Fort Myers

1 passenger, economy

Cheap flights Chicago to Fort Myers

Compare prices, duration and stops

American Airlines
AA 3238
00:07
Chicago, O'Hare International Airport (ORD)
Tue, 22 sep
3h 2min
Direct
03:09
Fort Myers, Southwest Florida International Airport (RSW)
Tue, 22 sep
S$242
American Airlines
AA 2437
11:50
Chicago, O'Hare International Airport (ORD)
Wed, 23 sep
2h 57min
Direct
14:47
Fort Myers, Southwest Florida International Airport (RSW)
Wed, 23 sep
S$225
United Airlines
UA 1740
12:05
Chicago, O'Hare International Airport (ORD)
Sat, 26 sep
3h 6min
Direct
15:11
Fort Myers, Southwest Florida International Airport (RSW)
Sat, 26 sep
S$280
Frontier Airlines
F9 2112
12:25
Chicago, O'Hare International Airport (ORD)
Sun, 4 oct
27h 26min
1 stop
15:51
Fort Myers, Southwest Florida International Airport (RSW)
Mon, 5 oct +1
S$207
United Airlines
UA 1740
12:05
Chicago, O'Hare International Airport (ORD)
Wed, 7 oct
3h 6min
Direct
15:11
Fort Myers, Southwest Florida International Airport (RSW)
Wed, 7 oct
S$188
Southwest Airlines
WN 2004
12:45
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
9h 15min
1 stop
22:00
Fort Myers, Southwest Florida International Airport (RSW)
Wed, 7 oct
S$212
Southwest Airlines
WN 4460 Best price
10:05
Chicago, Chicago Midway International Airport (MDW)
Thu, 8 oct
2h 40min
Direct
12:45
Fort Myers, Southwest Florida International Airport (RSW)
Thu, 8 oct
S$176
United Airlines
UA 1740
12:05
Chicago, O'Hare International Airport (ORD)
Thu, 8 oct
3h 6min
Direct
15:11
Fort Myers, Southwest Florida International Airport (RSW)
Thu, 8 oct
S$213
Southwest Airlines
WN 4566
21:35
Chicago, Chicago Midway International Airport (MDW)
Sat, 7 nov
2h 45min
Direct
00:20
Fort Myers, Southwest Florida International Airport (RSW)
Sun, 8 nov +1
S$225
American Airlines
AA 1784
12:45
Chicago, O'Hare International Airport (ORD)
Fri, 25 dec
7h 13min
1 stop
19:58
Fort Myers, Southwest Florida International Airport (RSW)
Fri, 25 dec
S$274

Low price calendar

September 2026
Price chart (September 2026)
min: S$225 · max: S$280
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S$225
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Cheap flights Chicago to Fort Myers

Southwest Airlines
Southwest Airlines
Wed, Thu, Sat
Price from
S$176
United Airlines
United Airlines
Wed, Thu, Sat
Price from
S$213
American Airlines
American Airlines
Tue, Wed, Fri
Price from
S$225

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
United States → United States
ORL
from
S$27
CHI
Chicago — Orlando
United States → United States
MCO
from
S$27
CHI
Chicago — Atlanta
United States → United States
ATL
from
S$28
CHI
Chicago — Houston
United States → United States
IAH
from
S$28
CHI
Chicago — Houston
United States → United States
HOU
from
S$28
CHI
Chicago — New York
United States → United States
NYC
from
S$30
CHI
Chicago — Denver
United States → United States
DEN
from
S$31
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
S$31
CHI
Chicago — Miami
United States → United States
MIA
from
S$32

Popular destinations to Fort Myers

All →
RDU
Raleigh — Fort Myers
United States → United States
FMY
from
S$97
CMH
Columbus — Fort Myers
United States → United States
FMY
from
S$103
ATL
Atlanta — Fort Myers
United States → United States
FMY
from
S$115
CVG
Cincinnati — Fort Myers
United States → United States
FMY
from
S$120
MSP
Minneapolis — Fort Myers
United States → United States
FMY
from
S$123
ISP
Islip — Fort Myers
United States → United States
FMY
from
S$126
PHL
Philadelphia — Fort Myers
United States → United States
FMY
from
S$134
WAS
Washington — Fort Myers
United States → United States
FMY
from
S$140

Cheap flights Chicago to Fort Myers

Interesting facts about the route

Flight time

3h 6min

Distance

1 805 km

Average price

S$225

Most frequent flight

UA 1740

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

S$11

Buy

change

2 GB

data

15

days

S$16

Buy

change

5 GB

data

30

days

S$18

Buy

change

3 GB

data

30

days

S$20

Buy

change

5 GB

data

30

days

S$29

Buy

Frequently Asked Questions

The average ticket price Chicago Fort Myers is S$225. The cheapest ticket costs S$242, operated by American Airlines, flight 3238, departing Chicago on 22 September at 00:07, arriving Fort Myers on 22 September at 03:09.
The average flight time is 3 hours 2 minutes.The fastest flight takes 3 hours 2 minutes, flight 3238operated by American Airlines, departing Chicago on 22 September at 00:07, arriving Fort Myers on 22 September at 03:09.
Flights on the Chicago - Fort Myers route are operated by the following airlines: American Airlines, United Airlines, Southwest Airlines.
The distance from Chicago to Fort Myers is 1805 km.