Find Cheap Flights from Houston Hobby & other airports to Chicago Midway (HOU - MDW)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Houston Hobby & other airports to Chicago Midway

(Round-trip)
Depart: Sat May 13 2017 Return: Tue May 16 2017 Trip spans 4 days
Delta
Delta
HOU
7:35a
MDW
12:55p
5h 20m
1 stop
MDW
5:10a
HOU
10:37a
5h 27m
1 stop
Depart: Tue May 16 2017 Return: Sat May 20 2017 Trip spans 5 days
Delta
Delta
HOU
11:45a
MDW
6:10p
6h 25m
1 stop
MDW
11:55a
HOU
7:53p
7h 58m
1 stop
Depart: Wed May 17 2017 Return: Fri May 19 2017 Trip spans 3 days
Delta
Delta
HOU
8:55a
MDW
1:59p
5h 04m
1 stop
MDW
5:10a
HOU
10:37a
5h 27m
1 stop
Depart: Sat May 20 2017 Return: Tue May 23 2017 Trip spans 4 days
Delta
Delta
HOU
5:15a
MDW
12:55p
7h 40m
1 stop
MDW
5:10a
HOU
10:37a
5h 27m
1 stop
Depart: Sat May 6 2017 Return: Wed May 10 2017 Trip spans 5 days
Delta
Delta
HOU
12:17p
MDW
6:19p
6h 02m
1 stop
MDW
6:21a
HOU
12:20p
5h 59m
1 stop
Depart: Mon May 8 2017 Return: Tue May 9 2017 Trip spans 2 days
Delta
Delta
HOU
12:45p
MDW
6:20p
5h 35m
1 stop
MDW
3:20a
HOU
8:10a
4h 50m
1 stop
Depart: Tue May 9 2017 Return: Wed May 17 2017 Trip spans 9 days
Delta
Delta
HOU
12:45p
MDW
6:20p
5h 35m
1 stop
MDW
3:20a
HOU
8:10a
4h 50m
1 stop
Depart: Wed May 10 2017 Return: Tue May 16 2017 Trip spans 7 days
Delta
Delta
HOU
4:25a
MDW
9:33a
5h 08m
1 stop
MDW
5:16a
HOU
10:35a
5h 19m
1 stop
Depart: Tue May 23 2017 Return: Wed Jun 7 2017 Trip spans 16 days
Delta
Delta
HOU
11:45a
MDW
6:20p
6h 35m
1 stop
MDW
7:04a
HOU
12:57p
5h 53m
1 stop
Depart: Thu May 11 2017 Return: Sun May 14 2017 Trip spans 4 days
Delta
Delta
HOU
5:15a
MDW
12:19p
7h 04m
1 stop
MDW
2:30a
HOU
8:18a
5h 48m
1 stop
Depart: Fri May 12 2017 Return: Sun May 14 2017 Trip spans 3 days
Delta
Delta
HOU
3:35a
MDW
10:45a
7h 10m
1 stop
MDW
2:30a
HOU
10:34a
8h 04m
1 stop
Depart: Sun May 7 2017 Return: Tue May 9 2017 Trip spans 3 days
Delta
Delta
HOU
3:15a
MDW
8:23a
5h 08m
1 stop
MDW
11:55a
HOU
4:53p
4h 58m
1 stop
Depart: Wed Jun 7 2017 Return: Sat Jun 10 2017 Trip spans 4 days
Delta
Delta
HOU
2:15a
MDW
7:38a
5h 23m
1 stop
MDW
1:32p
HOU
7:13p
5h 41m
1 stop
Depart: Mon Jun 19 2017 Return: Sat Jun 24 2017 Trip spans 6 days
Delta
Delta
HOU
11:32a
MDW
5:03p
5h 31m
1 stop
MDW
1:59p
HOU
7:09p
5h 10m
1 stop
Depart: Wed May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
Delta
Delta
HOU
3:15a
MDW
8:23a
5h 08m
1 stop
MDW
5:10a
HOU
10:37a
5h 27m
1 stop
Depart: Sun May 14 2017 Return: Mon May 15 2017 Trip spans 2 days
Delta
Delta
HOU
3:15a
MDW
8:11a
4h 56m
1 stop
MDW
1:32p
HOU
7:17p
5h 45m
1 stop
Depart: Tue Jun 27 2017 Return: Wed Jun 28 2017 Trip spans 2 days
Delta
Delta
HOU
3:10a
MDW
9:07a
5h 57m
1 stop
MDW
3:20a
HOU
10:55a
7h 35m
1 stop
Depart: Thu May 4 2017 Return: Sat May 13 2017 Trip spans 10 days
Delta
Delta
HOU
4:05a
MDW
11:20a
7h 15m
1 stop
MDW
1:52p
HOU
7:02p
5h 10m
1 stop
Depart: Fri May 5 2017 Return: Sat May 6 2017 Trip spans 2 days
Delta
Delta
HOU
3:15a
MDW
8:23a
5h 08m
1 stop
MDW
1:52p
HOU
7:53p
6h 01m
1 stop
Depart: Tue May 2 2017 Return: Fri May 5 2017 Trip spans 4 days
Delta
Delta
HOU
3:15a
MDW
9:33a
6h 18m
1 stop
MDW
6:21a
HOU
11:05a
4h 44m
1 stop
Select an airline:  Southwest
Direct flights HOU to MDW on Southwest
Flight # Depart HOU Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1658 5:20 am 7:45 am Jun 5 - Jun 30
4522 5:30 am 7:55 am Jun 4 - Aug 13
4281 6:05 am 8:30 am May 14 - May 21
4281 6:05 am 8:30 am Apr 30 - May 7
975 6:15 am 8:40 am May 30 - Jun 2
975 6:15 am 8:40 am Apr 26 - May 26
1614 6:50 am 9:15 am Jun 5 - Jun 30
1652 7:00 am 9:30 am Jun 4 - Aug 13
2944 7:30 am 9:55 am May 28 - May 28
443 7:30 am 9:55 am Apr 30 - May 21
624 7:45 am 10:10 am Apr 29 - Jun 3
974 7:50 am 10:15 am May 30 - Jun 2
974 7:50 am 10:15 am Apr 26 - May 26
974 8:40 am 11:10 am May 29 - May 29
1 8:45 am 11:15 am Jun 4 - Jun 4
4185 8:55 am 11:25 am Apr 30 - May 21
2019 9:40 am 12:05 pm May 13 - May 27
5 9:40 am 12:05 pm Jun 3 - Jun 3
543 10:40 am 1:10 pm Jun 5 - Aug 14
4185 11:40 am 2:05 pm May 28 - May 28
766 12:10 pm 2:35 pm May 9 - Jun 2
766 12:10 pm 2:35 pm Apr 26 - May 8
411 2:25 pm 4:50 pm Jun 5 - Jun 30
5276 2:25 pm 4:50 pm Jun 4 - Aug 13
1010 2:30 pm 4:55 pm May 29 - May 29
139 2:30 pm 4:55 pm Apr 26 - May 26
139 2:30 pm 4:55 pm May 30 - Jun 2
4355 2:40 pm 5:05 pm Apr 30 - May 28
479 3:20 pm 5:45 pm Apr 29 - Jun 3
174 4:00 pm 6:25 pm May 29 - May 29
1369 5:10 pm 7:35 pm Jun 4 - Jun 25
1845 5:10 pm 7:35 pm Apr 26 - May 8
1845 5:10 pm 7:35 pm May 9 - May 26
1845 5:10 pm 7:35 pm May 29 - May 29
1845 5:10 pm 7:35 pm May 30 - Jun 2
3361 5:20 pm 7:45 pm May 28 - May 28
3361 5:20 pm 7:45 pm Apr 30 - May 21
1375 5:30 pm 7:55 pm Jun 5 - Jun 30
4788 6:10 pm 8:35 pm Apr 29 - Jun 3
4586 7:15 pm 9:40 pm Apr 30 - May 21
4586 7:15 pm 9:40 pm May 28 - May 28
3274 7:40 pm 10:05 pm Jun 4 - Aug 13
502 8:30 pm 10:55 pm May 28 - May 28
184 8:40 pm 11:05 pm Jun 5 - Jun 30
5304 9:05 pm 11:30 pm Apr 29 - Jun 3
1598 10:05 pm 12:30 am Apr 26 - Jun 2
3549 10:10 pm 12:35 am Apr 30 - May 21
3425 10:15 pm 12:40 am Jun 4 - Aug 13
3999 10:35 pm 12:55 am Jun 5 - Jun 30
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Houston
$204
Destination

Chicago
$204
Airlines