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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

American Airlines
AA 2561
17:11
Chicago, O'Hare International Airport (ORD)
Wed, 16 sep
2h 56min
Direct
20:07
Fort Myers, Southwest Florida International Airport (RSW)
Wed, 16 sep
136 £
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
108 £
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
139 £
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
141 £
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
131 £
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
164 £
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
120 £
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
106 £
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
123 £
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
103 £
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
124 £
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
131 £
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
159 £

Low price calendar

September 2026
Price chart (September 2026)
min: 108 £ · max: 164 £
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136 £
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108 £
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139 £
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141 £
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Cheap flights Chicago to Southwest Florida International Airport

Southwest Airlines
Southwest Airlines
Wed, Thu, Sat
Price from
£103
United Airlines
United Airlines
Wed, Thu, Sat
Price from
£106
American Airlines
American Airlines
Tue, Wed, Fri
Price from
£131
TEM Enterprises Dba XTRAirways
TEM Enterprises Dba XTRAirways
Sat
Price from
£139

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
United States → United States
ORL
from
£16
CHI
Chicago — Orlando
United States → United States
MCO
from
£16
CHI
Chicago — Atlanta
United States → United States
ATL
from
£16
CHI
Chicago — Houston
United States → United States
IAH
from
£17
CHI
Chicago — Houston
United States → United States
HOU
from
£17
CHI
Chicago — New York
United States → United States
NYC
from
£17
CHI
Chicago — Denver
United States → United States
DEN
from
£18
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
£18
CHI
Chicago — Miami
United States → United States
MIA
from
£18

Popular destinations to Southwest Florida International Airport

All →
RDU
Raleigh — Fort Myers
United States → United States
RSW
from
£57
CMH
Columbus — Fort Myers
United States → United States
RSW
from
£60
ATL
Atlanta — Fort Myers
United States → United States
RSW
from
£67
CVG
Cincinnati — Fort Myers
United States → United States
RSW
from
£70
MSP
Minneapolis — Fort Myers
United States → United States
RSW
from
£72
ISP
Islip — Fort Myers
United States → United States
RSW
from
£73
PHL
Philadelphia — Fort Myers
United States → United States
RSW
from
£78
WAS
Washington — Fort Myers
United States → United States
RSW
from
£81

Cheap flights Chicago to Southwest Florida International Airport

Interesting facts about the route

Flight time

3h 6min

Distance

1 805 km

Average price

£131

Most frequent flight

AA 2561

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

£7

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change

2 GB

data

15

days

£9

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change

5 GB

data

30

days

£10

Buy

change

3 GB

data

30

days

£12

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change

5 GB

data

30

days

£17

Buy

Frequently Asked Questions

The average ticket price Chicago Southwest Florida International Airport is £131. The cheapest ticket costs £108, 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 56 minutes, flight 2561 operated by American Airlines, departing Chicago on 16 September at 17:11, arriving Southwest Florida International Airport on 16 September at 20:07.
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.