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Cheap flights Houston (William P. Hobby) to Chicago Midway International Airport

1 passenger, economy

Cheap flights Houston to Chicago Midway International Airport

Compare prices, duration and stops

Frontier Airlines
F9 1404
11:28
Houston, George Bush Intercontinental Airport (IAH)
Tue, 15 sep
11h 18min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
242 S$
Frontier Airlines
F9 1404
11:28
Houston, George Bush Intercontinental Airport (IAH)
Wed, 16 sep
11h 23min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
198 S$
Frontier Airlines
F9 1404
11:08
Houston, George Bush Intercontinental Airport (IAH)
Sat, 19 sep
11h 43min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
229 S$
Southwest Airlines
WN 149
12:00
Houston, William P. Hobby (HOU)
Sat, 19 sep
2h 25min
Direct
14:25
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
134 S$
Frontier Airlines
F9 4076
17:08
Houston, George Bush Intercontinental Airport (IAH)
Mon, 21 sep
5h 43min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
204 S$
Southwest Airlines
WN 2771
00:55
Houston, William P. Hobby (HOU)
Tue, 22 sep
2h 25min
Direct
03:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
187 S$
Frontier Airlines
F9 1404
11:28
Houston, George Bush Intercontinental Airport (IAH)
Wed, 23 sep
11h 23min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
159 S$
Frontier Airlines
F9 1404 Best price
11:28
Houston, George Bush Intercontinental Airport (IAH)
Wed, 30 sep
11h 23min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
107 S$
Frontier Airlines
F9 1404
10:55
Houston, George Bush Intercontinental Airport (IAH)
Thu, 8 oct
11h 50min
1 stop
22:45
Chicago, Chicago Midway International Airport (MDW)
Thu, 8 oct
129 S$
Southwest Airlines
WN 050
23:30
Houston, William P. Hobby (HOU)
Mon, 12 oct
6h 35min
1 stop
06:05
Chicago, Chicago Midway International Airport (MDW)
Tue, 13 oct +1
133 S$
Southwest Airlines
WN 43
23:45
Houston, William P. Hobby (HOU)
Mon, 19 oct
2h 25min
Direct
02:10
Chicago, Chicago Midway International Airport (MDW)
Tue, 20 oct +1
206 S$
Southwest Airlines
WN 4789
00:55
Houston, William P. Hobby (HOU)
Tue, 20 oct
2h 25min
Direct
03:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 20 oct
122 S$
Frontier Airlines
F9 4076
18:28
Houston, George Bush Intercontinental Airport (IAH)
Sat, 24 oct
10h 15min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Sun, 25 oct +1
174 S$
Frontier Airlines
F9 1404
11:05
Houston, George Bush Intercontinental Airport (IAH)
Sat, 31 oct
11h 42min
1 stop
22:47
Chicago, Chicago Midway International Airport (MDW)
Sat, 31 oct
174 S$
Frontier Airlines
F9 4076
19:35
Houston, George Bush Intercontinental Airport (IAH)
Tue, 17 nov
8h 18min
1 stop
03:53
Chicago, Chicago Midway International Airport (MDW)
Wed, 18 nov +1
123 S$
Frontier Airlines
F9 2030
11:01
Houston, George Bush Intercontinental Airport (IAH)
Fri, 27 nov
14h 46min
1 stop
01:47
Chicago, Chicago Midway International Airport (MDW)
Sat, 28 nov +1
173 S$
Southwest Airlines
WN 1044
11:05
Houston, William P. Hobby (HOU)
Sat, 28 nov
2h 25min
Direct
13:30
Chicago, Chicago Midway International Airport (MDW)
Sat, 28 nov
288 S$
Southwest Airlines
WN 2246
05:15
Houston, William P. Hobby (HOU)
Mon, 30 nov
7h 35min
1 stop
12:50
Chicago, Chicago Midway International Airport (MDW)
Mon, 30 nov
312 S$
Southwest Airlines
WN 1654
04:20
Houston, William P. Hobby (HOU)
Sun, 20 dec
2h 25min
Direct
06:45
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 dec
176 S$
Southwest Airlines
WN 1044
11:10
Houston, William P. Hobby (HOU)
Sun, 20 dec
2h 25min
Direct
13:35
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 dec
233 S$
Southwest Airlines
WN 2174
17:00
Houston, William P. Hobby (HOU)
Wed, 30 dec
3h 45min
1 stop
20:45
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 dec
143 S$
Eagle Aviation
Y4 1731
15:39
Houston, George Bush Intercontinental Airport (IAH)
Mon, 28 June
31h 12min
3 stops
22:51
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 June +1
615 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 107 S$ · max: 242 S$
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242 S$
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198 S$
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229 S$
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204 S$
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187 S$
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159 S$
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Good deal
107 S$

Cheap flights Houston to Chicago Midway International Airport

Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Sat, Sun
Price from
S$133
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
S$159
Eagle Aviation
Eagle Aviation
Mon
Price from
S$615

Popular destinations from Houston

All →
HOU
Houston — Atlanta
United States → United States
ATL
from
S$24
HOU
Houston — Chicago
United States → United States
ORD
from
S$27
HOU
Houston — Chicago
United States → United States
CHI
from
S$27
HOU
Houston — Miami
United States → United States
MIA
from
S$29
HOU
Houston — Orlando
United States → United States
ORL
from
S$36
HOU
Houston — Los Angeles
United States → United States
LAX
from
S$41
HOU
Houston — Las Vegas
United States → United States
LAS
from
S$44
HOU
Houston — Fort Lauderdale
United States → United States
FLL
from
S$44
HOU
Houston — Orlando
United States → United States
MCO
from
S$47

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
DFW
Dallas — Chicago
United States → United States
MDW
from
S$89
PHL
Philadelphia — Chicago
United States → United States
MDW
from
S$90
TPA
Tampa — Chicago
United States → United States
MDW
from
S$94
MIA
Miami — Chicago
United States → United States
MDW
from
S$96
DEN
Denver — Chicago
United States → United States
MDW
from
S$97

Cheap flights Houston to Chicago Midway International Airport

Interesting facts about the route

Flight time

7h 8min

Distance

1 478 km

Average price

S$181

Most frequent flight

F9 1404

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 Houston Chicago Midway International Airport is S$181. The cheapest ticket costs S$198, operated by Frontier Airlines, flight 1404, departing Houston on 16 September at 11:28, arriving Chicago Midway International Airport on 16 September at 22:51.
The average flight time is 11 hours 23 minutes. The fastest flight takes 11 hours 18 minutes, flight 1404 operated by Frontier Airlines, departing Houston on 15 September at 11:28, arriving Chicago Midway International Airport on 15 September at 22:46.
Flights on the Houston - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines, Eagle Aviation.
The distance from Houston to Chicago Midway International Airport is 1478 km.