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Cheap flights Chicago to Southwest Florida International Airport

1 passenger, economy

Cheap flights Chicago to Southwest Florida International Airport

Compare prices, duration and stops

Southwest Airlines
WN 1094
18:05
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
6h 55min
1 stop
01:00
Fort Myers, Southwest Florida International Airport (RSW)
Fri, 18 sep +1
185 S$
Southwest Airlines
WN 356
23:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
2h 50min
Direct
02:05
Fort Myers, Southwest Florida International Airport (RSW)
Fri, 18 sep +1
367 S$
United Airlines
UA 1740
12:15
Chicago, O'Hare International Airport (ORD)
Fri, 18 sep
3h 6min
Direct
15:21
Fort Myers, Southwest Florida International Airport (RSW)
Fri, 18 sep
282 S$
TEM Enterprises Dba XTRAirways
XP 422
00:17
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
22h 34min
1 stop
22:51
Fort Myers, Southwest Florida International Airport (RSW)
Sat, 19 sep
238 S$
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
242 S$
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
225 S$
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
279 S$
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
206 S$
United Airlines
UA 1740 🔥 Hot deal
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
181 S$
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
212 S$
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
176 S$
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
212 S$
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
225 S$
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
274 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 185 S$ · max: 282 S$
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185 S$
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282 S$
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238 S$
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242 S$
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225 S$
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Cheap flights Chicago to Southwest Florida International Airport

Southwest Airlines
Southwest Airlines
Wed, Thu, Sat
Price from
S$176
United Airlines
United Airlines
Wed, Thu, Fri, Sat
Price from
S$181
American Airlines
American Airlines
Tue, Wed, Fri
Price from
S$225
TEM Enterprises Dba XTRAirways
TEM Enterprises Dba XTRAirways
Sat
Price from
S$238

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$31

Popular destinations to Southwest Florida International Airport

All →
RDU
Raleigh — Fort Myers
United States → United States
RSW
from
S$97
CMH
Columbus — Fort Myers
United States → United States
RSW
from
S$103
ATL
Atlanta — Fort Myers
United States → United States
RSW
from
S$115
CVG
Cincinnati — Fort Myers
United States → United States
RSW
from
S$120
MSP
Minneapolis — Fort Myers
United States → United States
RSW
from
S$123
ISP
Islip — Fort Myers
United States → United States
RSW
from
S$126
PHL
Philadelphia — Fort Myers
United States → United States
RSW
from
S$133
WAS
Washington — Fort Myers
United States → United States
RSW
from
S$139

Cheap flights Chicago to Southwest Florida International Airport

Interesting facts about the route

Flight time

3h 6min

Distance

1 805 km

Average price

S$225

Most frequent flight

WN 1094

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 Southwest Florida International Airport is S$225. The cheapest ticket costs S$185, operated by Southwest Airlines, flight 1094, departing Chicago on 17 September at 18:05, arriving Southwest Florida International Airport on 18 September at 01:00.
The average flight time is 6 hours 55 minutes. The fastest flight takes 2 hours 50 minutes, flight 356 operated by Southwest Airlines, departing Chicago on 17 September at 23:15, arriving Southwest Florida International Airport on 18 September at 02:05.
Flights on the Chicago - Southwest Florida International Airport route are operated by the following airlines: American Airlines, United Airlines, Southwest Airlines, TEM Enterprises Dba XTRAirways.
The distance from Chicago to Southwest Florida International Airport is 1805 km.