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Cheap flights Tampa to Chicago Midway International Airport

1 passenger, economy

Cheap flights Tampa to Chicago Midway International Airport

Compare prices, duration and stops

Southwest Airlines
WN 2040
09:50
Tampa (TPA)
Sun, 13 sep
6h 5min
1 stop
15:55
Chicago, Chicago Midway International Airport (MDW)
Sun, 13 sep
201 S$
Frontier Airlines
F9 1853
11:15
Tampa (TPA)
Sun, 13 sep
11h 31min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Sun, 13 sep
209 S$
Frontier Airlines
F9 4435
16:59
Tampa (TPA)
Sun, 13 sep
5h 47min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Sun, 13 sep
190 S$
Frontier Airlines
F9 2723
22:00
Tampa (TPA)
Mon, 14 sep
6h 44min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep +1
204 S$
Frontier Airlines
F9 4435
18:03
Tampa (TPA)
Tue, 15 sep
4h 43min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
173 S$
Frontier Airlines
F9 4435
18:10
Tampa (TPA)
Wed, 16 sep
4h 41min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
186 S$
Frontier Airlines
F9 4435
16:59
Tampa (TPA)
Thu, 17 sep
5h 47min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
203 S$
Frontier Airlines
F9 2723
22:00
Tampa (TPA)
Thu, 17 sep
6h 44min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep +1
222 S$
Frontier Airlines
F9 4435
16:59
Tampa (TPA)
Fri, 18 sep
5h 52min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep
203 S$
Frontier Airlines
F9 2723
22:00
Tampa (TPA)
Fri, 18 sep
6h 44min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep +1
166 S$
Frontier Airlines
F9 4435
16:59
Tampa (TPA)
Sun, 20 sep
5h 47min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
162 S$
Frontier Airlines
F9 2723
22:00
Tampa (TPA)
Sun, 20 sep
6h 44min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep +1
165 S$
Frontier Airlines
F9 2723
22:00
Tampa (TPA)
Mon, 21 sep
6h 44min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep +1
163 S$
Frontier Airlines
F9 4435
18:03
Tampa (TPA)
Tue, 29 sep
4h 43min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
128 S$
Frontier Airlines
F9 4435 🔥 Hot deal Best price
16:59
Tampa (TPA)
Thu, 1 oct
5h 47min
Direct
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
98 S$
Frontier Airlines
F9 2723 Best price
22:00
Tampa (TPA)
Thu, 1 oct
6h 44min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Fri, 2 oct +1
98 S$
Frontier Airlines
F9 4435
16:52
Tampa (TPA)
Sat, 3 oct
5h 59min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
151 S$
Frontier Airlines
F9 2723
22:00
Tampa (TPA)
Mon, 5 oct
6h 43min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct +1
135 S$
Frontier Airlines
F9 4435
16:52
Tampa (TPA)
Tue, 6 oct
5h 54min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct
128 S$
Southwest Airlines
WN 2107
10:55
Tampa (TPA)
Sat, 10 oct
6h 10min
1 stop
17:05
Chicago, Chicago Midway International Airport (MDW)
Sat, 10 oct
137 S$
Frontier Airlines
F9 4435
18:05
Tampa (TPA)
Tue, 3 nov
5h 42min
1 stop
23:47
Chicago, Chicago Midway International Airport (MDW)
Tue, 3 nov
143 S$
Frontier Airlines
F9 4435
17:54
Tampa (TPA)
Mon, 9 nov
5h 53min
1 stop
23:47
Chicago, Chicago Midway International Airport (MDW)
Mon, 9 nov
156 S$
Frontier Airlines
F9 2723
22:57
Tampa (TPA)
Mon, 9 nov
6h 50min
1 stop
05:47
Chicago, Chicago Midway International Airport (MDW)
Tue, 10 nov +1
171 S$
Frontier Airlines
F9 4435
18:00
Tampa (TPA)
Tue, 10 nov
5h 47min
1 stop
23:47
Chicago, Chicago Midway International Airport (MDW)
Tue, 10 nov
127 S$
Frontier Airlines
F9 4435
18:05
Tampa (TPA)
Tue, 10 nov
5h 42min
1 stop
23:47
Chicago, Chicago Midway International Airport (MDW)
Tue, 10 nov
149 S$
Frontier Airlines
F9 2723
22:57
Tampa (TPA)
Fri, 13 nov
6h 50min
1 stop
05:47
Chicago, Chicago Midway International Airport (MDW)
Sat, 14 nov +1
150 S$
Southwest Airlines
WN 2899
12:20
Tampa (TPA)
Thu, 19 nov
2h 45min
Direct
15:05
Chicago, Chicago Midway International Airport (MDW)
Thu, 19 nov
138 S$
Southwest Airlines
WN 3029
23:10
Tampa (TPA)
Tue, 24 nov
2h 45min
Direct
01:55
Chicago, Chicago Midway International Airport (MDW)
Wed, 25 nov +1
218 S$
Southwest Airlines
WN 897
04:25
Tampa (TPA)
Mon, 30 nov
8h 10min
1 stop
12:35
Chicago, Chicago Midway International Airport (MDW)
Mon, 30 nov
332 S$
Southwest Airlines
WN 4265
01:00
Tampa (TPA)
Tue, 22 dec
2h 50min
Direct
03:50
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 dec
173 S$
Southwest Airlines
WN 3907
12:30
Tampa (TPA)
Wed, 3 feb
2h 45min
Direct
15:15
Chicago, Chicago Midway International Airport (MDW)
Wed, 3 feb
169 S$
Southwest Airlines
WN 3907
11:45
Tampa (TPA)
Sun, 28 feb
2h 45min
Direct
14:30
Chicago, Chicago Midway International Airport (MDW)
Sun, 28 feb
255 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 128 S$ · max: 204 S$
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Wed
Thu
Fri
Sat
Sun
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190 S$
14
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204 S$
15
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173 S$
16
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186 S$
17
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203 S$
18
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166 S$
19
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20
Good deal
162 S$
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163 S$
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Good deal
128 S$
30
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Cheap flights Tampa to Chicago Midway International Airport

Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$98
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Sat, Sun
Price from
S$137

Popular destinations from Tampa

All →
TPA
Tampa — Atlanta
United States → United States
ATL
from
S$33
TPA
Tampa — Philadelphia
United States → United States
PHL
from
S$33
TPA
Tampa — Philadelphia
United States → United States
TTN
from
S$38
TPA
Tampa — Cleveland
United States → United States
CLE
from
S$48
TPA
Tampa — Key West
United States → United States
EYW
from
S$48
TPA
Tampa — Chattanooga
United States → United States
CHA
from
S$51
TPA
Tampa — Chicago
United States → United States
CHI
from
S$52
TPA
Tampa — Greenville
United States → United States
GSP
from
S$55
TPA
Tampa — Cincinnati
United States → United States
CVG
from
S$56

Popular destinations to Chicago Midway International Airport

All →
NYC
New York — Chicago
United States → United States
MDW
from
S$28
ATL
Atlanta — Chicago
United States → United States
MDW
from
S$47
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
S$69
HOU
Houston — Chicago
United States → United States
MDW
from
S$76
DFW
Dallas — Chicago
United States → United States
MDW
from
S$89
PHL
Philadelphia — Chicago
United States → United States
MDW
from
S$90
MIA
Miami — Chicago
United States → United States
MDW
from
S$96
DEN
Denver — Chicago
United States → United States
MDW
from
S$97

Cheap flights Tampa to Chicago Midway International Airport

Interesting facts about the route

Flight time

5h 52min

Distance

1 606 km

Average price

S$166

Most frequent flight

F9 4435

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 Tampa Chicago Midway International Airport is S$166. The cheapest ticket costs S$173, operated by Frontier Airlines, flight 4435, departing Tampa on 15 September at 18:03, arriving Chicago Midway International Airport on 15 September at 22:46.
The average flight time is 6 hours 5 minutes. The fastest flight takes 4 hours 43 minutes, flight 4435 operated by Frontier Airlines, departing Tampa on 15 September at 18:03, arriving Chicago Midway International Airport on 15 September at 22:46.
Flights on the Tampa - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.
The distance from Tampa to Chicago Midway International Airport is 1606 km.