Find Deals on 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
Students
under 26
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: Sun Dec 11 2016 Return: Tue Dec 13 2016 Trip spans 3 days
Delta
Delta
HOU
1:00a
MDW
6:43a
5h 43m
1 stop
MDW
7:20a
HOU
12:55p
5h 35m
1 stop
Depart: Sat Dec 10 2016 Return: Tue Dec 13 2016 Trip spans 4 days
Major Airline
Major Airline
HOU
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
8:00a
HOU
9:50a
1h 50m
nonstop
Depart: Mon Dec 12 2016 Return: Wed Dec 14 2016 Trip spans 3 days
Delta
Delta
HOU
9:13a
MDW
2:09p
4h 56m
1 stop
MDW
5:20a
HOU
10:10a
4h 50m
1 stop
Depart: Tue Dec 13 2016 Return: Wed Dec 14 2016 Trip spans 2 days
Delta
Delta
HOU
3:15a
MDW
8:24a
5h 09m
1 stop
MDW
4:19a
HOU
9:32a
5h 13m
1 stop
Depart: Wed Dec 14 2016 Return: Fri Jan 6 2017 Trip spans 24 days
Delta
Delta
HOU
2:00a
MDW
8:24a
6h 24m
1 stop
MDW
10:16a
HOU
3:50p
5h 34m
1 stop
Depart: Wed Jan 4 2017 Return: Sun Jan 8 2017 Trip spans 5 days
Delta
Delta
HOU
1:00a
MDW
6:45a
5h 45m
1 stop
MDW
10:29a
HOU
6:07p
7h 38m
1 stop
Depart: Fri Jan 6 2017 Return: Sun Jan 8 2017 Trip spans 3 days
Delta
Delta
HOU
2:20a
MDW
7:22a
5h 02m
1 stop
MDW
10:29a
HOU
6:07p
7h 38m
1 stop
Depart: Mon Jan 9 2017 Return: Wed Jan 11 2017 Trip spans 3 days
Delta
Delta
HOU
1:40a
MDW
8:33a
6h 53m
1 stop
MDW
10:40a
HOU
5:48p
7h 08m
1 stop
Depart: Tue Jan 10 2017 Return: Thu Jan 12 2017 Trip spans 3 days
Delta
Delta
HOU
2:00a
MDW
8:33a
6h 33m
1 stop
MDW
7:20a
HOU
12:59p
5h 39m
1 stop
Depart: Wed Jan 11 2017 Return: Fri Jan 20 2017 Trip spans 10 days
Delta
Delta
HOU
5:18a
MDW
10:03a
4h 45m
1 stop
MDW
7:20a
HOU
12:50p
5h 30m
1 stop
Depart: Thu Jan 12 2017 Return: Sun Jan 15 2017 Trip spans 4 days
Delta
Delta
HOU
2:00a
MDW
8:33a
6h 33m
1 stop
MDW
3:45a
HOU
9:45a
6h 00m
1 stop
Depart: Fri Jan 13 2017 Return: Sun Jan 15 2017 Trip spans 3 days
Delta
Delta
HOU
1:30a
MDW
9:54a
8h 24m
1 stop
MDW
3:45a
HOU
9:45a
6h 00m
1 stop
Depart: Sat Jan 14 2017 Return: Mon Jan 30 2017 Trip spans 17 days
Delta
Delta
HOU
7:00a
MDW
12:19p
5h 19m
1 stop
MDW
7:20a
HOU
12:50p
5h 30m
1 stop
Depart: Tue Jan 17 2017 Return: Wed Jan 18 2017 Trip spans 2 days
Delta
Delta
HOU
12:20p
MDW
5:46p
5h 26m
1 stop
MDW
9:08a
HOU
2:07p
4h 59m
1 stop
Depart: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Delta
Delta
HOU
10:18a
MDW
4:00p
5h 42m
1 stop
MDW
3:30a
HOU
9:43a
6h 13m
1 stop
Depart: Mon Jan 23 2017 Return: Thu Jan 26 2017 Trip spans 4 days
Delta
Delta
HOU
12:07p
MDW
5:46p
5h 39m
1 stop
MDW
7:20a
HOU
12:50p
5h 30m
1 stop
Depart: Fri Jan 27 2017 Return: Sun Jan 29 2017 Trip spans 3 days
Delta
Delta
HOU
12:03p
MDW
5:46p
5h 43m
1 stop
MDW
3:45a
HOU
9:43a
5h 58m
1 stop
Depart: Sat Jan 28 2017 Return: Tue Jan 31 2017 Trip spans 4 days
Delta
Delta
HOU
2:15a
MDW
8:01a
5h 46m
1 stop
MDW
12:59p
HOU
6:49p
5h 50m
1 stop
Depart: Thu Feb 2 2017 Return: Sun Feb 5 2017 Trip spans 4 days
Delta
Delta
HOU
2:00a
MDW
8:33a
6h 33m
1 stop
MDW
12:59p
HOU
6:46p
5h 47m
1 stop
Depart: Fri Feb 3 2017 Return: Mon Feb 6 2017 Trip spans 4 days
Delta
Delta
HOU
8:10a
MDW
3:02p
6h 52m
1 stop
MDW
12:26p
HOU
6:07p
5h 41m
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
1924 5:10 am 7:30 am Dec 21 - Jan 2
455 5:35 am 8:00 am Jan 5 - Jan 13
1575 5:50 am 8:10 am Jan 3 - Jan 4
1774 5:50 am 8:10 am Jan 1 - Jan 1
291 5:50 am 8:10 am Dec 4 - Dec 16
692 5:50 am 8:10 am Dec 18 - Dec 20
5805 5:55 am 8:15 am Dec 17 - Dec 17
6329 6:30 am 8:50 am Dec 21 - Jan 2
3898 6:50 am 9:10 am Dec 31 - Dec 31
841 6:50 am 9:10 am Dec 24 - Dec 24
5655 7:05 am 9:30 am Jan 8 - Jan 29
1940 7:25 am 9:50 am Jan 7 - Mar 4
1490 7:35 am 10:10 am Dec 17 - Dec 17
1771 7:35 am 10:00 am Jan 5 - Feb 13
1628 7:40 am 10:05 am Dec 21 - Jan 2
6426 8:35 am 11:00 am Dec 31 - Dec 31
1367 8:50 am 11:15 am Dec 24 - Dec 24
5785 9:20 am 11:55 am Dec 17 - Dec 17
825 9:30 am 11:55 am Jan 5 - Mar 8
3007 9:35 am 12:05 pm Jan 8 - Jan 29
3201 9:35 am 12:05 pm Jan 7 - Mar 4
3979 9:45 am 12:10 pm Dec 4 - Dec 18
3979 9:45 am 12:10 pm Jan 1 - Jan 1
1374 10:00 am 12:25 pm Dec 15 - Dec 20
1374 10:00 am 12:25 pm Jan 3 - Jan 3
5117 10:05 am 12:30 pm Dec 5 - Dec 14
5117 10:05 am 12:30 pm Jan 4 - Jan 4
2307 10:35 am 1:00 pm Dec 31 - Dec 31
526 10:35 am 1:00 pm Dec 24 - Dec 24
3 11:40 am 2:05 pm Jan 7 - Mar 4
4316 11:45 am 2:10 pm Dec 21 - Jan 2
4522 1:25 pm 3:50 pm Jan 7 - Mar 4
2134 2:00 pm 4:20 pm Dec 21 - Jan 2
867 2:20 pm 4:45 pm Jan 8 - Jan 29
867 2:20 pm 4:45 pm Jan 5 - Feb 13
5795 2:30 pm 4:50 pm Dec 17 - Dec 17
1573 2:40 pm 5:00 pm Dec 25 - Dec 25
2511 2:40 pm 5:00 pm Dec 5 - Dec 14
2511 2:40 pm 5:00 pm Dec 15 - Dec 16
2511 2:40 pm 5:00 pm Dec 18 - Dec 20
2511 2:40 pm 5:00 pm Jan 4 - Jan 4
2511 2:40 pm 5:00 pm Jan 1 - Jan 3
634 2:40 pm 5:00 pm Dec 24 - Dec 24
3620 2:50 pm 5:10 pm Dec 31 - Dec 31
787 4:10 pm 6:35 pm Dec 21 - Jan 2
4626 5:05 pm 7:35 pm Jan 5 - Jan 5
4626 5:10 pm 7:40 pm Jan 6 - Mar 8
3655 5:30 pm 8:00 pm Jan 8 - Jan 29
2310 5:40 pm 8:00 pm Dec 25 - Dec 25
417 5:40 pm 8:00 pm Jan 1 - Jan 4
417 5:40 pm 8:00 pm Dec 4 - Dec 20
6284 5:55 pm 8:15 pm Dec 24 - Dec 24
962 6:25 pm 8:45 pm Dec 17 - Dec 17
5890 6:30 pm 8:50 pm Dec 29 - Jan 2
5890 6:30 pm 8:50 pm Dec 21 - Dec 28
2283 8:05 pm 10:25 pm Dec 4 - Dec 20
2283 8:05 pm 10:25 pm Jan 1 - Jan 4
3221 8:05 pm 10:25 pm Dec 25 - Dec 25
948 8:05 pm 10:35 pm Jan 8 - Jan 29
157 8:30 pm 10:55 pm Jan 5 - Feb 13
1606 8:50 pm 11:10 pm Dec 24 - Dec 24
2191 9:15 pm 11:35 pm Dec 17 - Dec 17
4285 9:30 pm 11:50 pm Jan 8 - Jan 29
3110 9:55 pm 12:15 am Dec 4 - Dec 20
3110 9:55 pm 12:15 am Jan 1 - Jan 4
3588 10:00 pm 12:20 am Dec 25 - Dec 25
5460 10:30 pm 12:50 am Dec 21 - Jan 2
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

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
$208
Destination

Chicago
$208
Airlines