Find Cheap Flights to Chicago Midway

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 Sep 9 2017 Return: Tue Sep 12 2017 Trip spans 4 days
Delta
Delta
HOU
9:59a
MDW
4:49p
6h 50m
1 stop
MDW
10:06a
HOU
4:20p
6h 14m
1 stop
Depart: Tue Sep 12 2017 Return: Fri Sep 15 2017 Trip spans 4 days
Delta
Delta
HOU
3:30a
MDW
8:20a
4h 50m
1 stop
MDW
5:08a
HOU
10:20a
5h 12m
1 stop
Depart: Wed Sep 13 2017 Return: Tue Sep 19 2017 Trip spans 7 days
Delta
Delta
HOU
4:00a
MDW
9:31a
5h 31m
1 stop
MDW
3:25a
HOU
8:19a
4h 54m
1 stop
Depart: Sat Sep 16 2017 Return: Tue Sep 19 2017 Trip spans 4 days
Delta
Delta
HOU
4:20a
MDW
9:30a
5h 10m
1 stop
MDW
2:15p
HOU
7:06p
4h 51m
1 stop
Depart: Sun Sep 17 2017 Return: Tue Sep 19 2017 Trip spans 3 days
Delta
Delta
HOU
10:18a
MDW
6:16p
7h 58m
1 stop
MDW
5:05a
HOU
10:33a
5h 28m
1 stop
Depart: Mon Sep 18 2017 Return: Thu Sep 21 2017 Trip spans 4 days
Delta
Delta
HOU
11:05a
MDW
4:56p
5h 51m
1 stop
MDW
6:17a
HOU
12:28p
6h 11m
1 stop
Depart: Tue Sep 19 2017 Return: Wed Sep 20 2017 Trip spans 2 days
Delta
Delta
HOU
11:30a
MDW
6:55p
7h 25m
1 stop
MDW
5:05a
HOU
10:33a
5h 28m
1 stop
Depart: Wed Sep 20 2017 Return: Sat Sep 23 2017 Trip spans 4 days
Delta
Delta
HOU
2:00a
MDW
7:24a
5h 24m
1 stop
MDW
2:00a
HOU
6:32a
4h 32m
1 stop
Depart: Sat Sep 23 2017 Return: Mon Sep 25 2017 Trip spans 3 days
Delta
Delta
HOU
12:59p
MDW
6:54p
5h 55m
1 stop
MDW
12:15p
HOU
7:07p
6h 52m
1 stop
Depart: Mon Sep 25 2017 Return: Tue Sep 26 2017 Trip spans 2 days
Delta
Delta
HOU
1:10p
MDW
6:55p
5h 45m
1 stop
MDW
6:17a
HOU
12:28p
6h 11m
1 stop
Depart: Tue Sep 26 2017 Return: Fri Sep 29 2017 Trip spans 4 days
Delta
Delta
HOU
4:20a
MDW
9:31a
5h 11m
1 stop
MDW
2:15p
HOU
7:06p
4h 51m
1 stop
Depart: Thu Sep 28 2017 Return: Mon Oct 2 2017 Trip spans 5 days
Delta
Delta
HOU
3:30a
MDW
10:26a
6h 56m
1 stop
MDW
11:18a
HOU
4:51p
5h 33m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
Delta
Delta
HOU
10:18a
MDW
6:16p
7h 58m
1 stop
MDW
11:18a
HOU
4:51p
5h 33m
1 stop
Depart: Sat Sep 30 2017 Return: Tue Oct 3 2017 Trip spans 4 days
Delta
Delta
HOU
4:00a
MDW
9:30a
5h 30m
1 stop
MDW
6:17a
HOU
10:51a
4h 34m
1 stop
Depart: Mon Oct 2 2017 Return: Tue Oct 3 2017 Trip spans 2 days
Delta
Delta
HOU
12:59p
MDW
6:40p
5h 41m
1 stop
MDW
12:26p
HOU
7:10p
6h 44m
1 stop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Delta
Delta
HOU
10:07a
MDW
6:12p
8h 05m
1 stop
MDW
2:18p
HOU
7:05p
4h 47m
1 stop
Depart: Thu Nov 9 2017 Return: Mon Nov 13 2017 Trip spans 5 days
Delta
Delta
HOU
2:00a
MDW
9:49a
7h 49m
1 stop
MDW
8:10a
HOU
3:40p
7h 30m
1 stop
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
Delta
Delta
HOU
6:00a
MDW
12:55p
6h 55m
1 stop
MDW
10:17a
HOU
3:49p
5h 32m
1 stop
Depart: Thu Nov 16 2017 Return: Mon Nov 20 2017 Trip spans 5 days
Delta
Delta
HOU
2:00a
MDW
9:49a
7h 49m
1 stop
MDW
7:56a
HOU
3:49p
7h 53m
1 stop
Depart: Mon Nov 20 2017 Return: Tue Nov 28 2017 Trip spans 9 days
Delta
Delta
HOU
12:20p
MDW
5:55p
5h 35m
1 stop
MDW
10:10a
HOU
3:40p
5h 30m
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
507 5:35 am 8:00 am Sep 5 - Sep 29
507 5:35 am 8:00 am Aug 21 - Sep 1
4198 6:00 am 8:25 am Sep 10 - Sep 24
2213 6:50 am 9:20 am Sep 2 - Sep 2
29 6:50 am 9:20 am Sep 9 - Sep 23
2945 6:50 am 9:20 am Sep 3 - Sep 3
1720 7:15 am 9:40 am Sep 4 - Sep 4
304 7:15 am 9:40 am Sep 5 - Sep 29
304 7:15 am 9:40 am Aug 21 - Sep 1
4201 8:45 am 11:15 am Sep 10 - Sep 24
3838 9:55 am 12:25 pm Sep 2 - Sep 2
4177 9:55 am 12:25 pm Sep 9 - Sep 23
3862 10:10 am 12:40 pm Sep 3 - Sep 3
1037 10:45 am 1:15 pm Sep 4 - Sep 4
1037 10:45 am 1:15 pm Aug 21 - Sep 1
1037 10:45 am 1:15 pm Sep 5 - Sep 29
6318 11:45 am 2:15 pm Aug 21 - Sep 1
4245 1:00 pm 3:25 pm Sep 2 - Sep 2
4719 1:00 pm 3:25 pm Sep 9 - Sep 23
356 2:20 pm 4:50 pm Sep 4 - Sep 4
6013 2:25 pm 4:55 pm Sep 5 - Sep 29
6013 2:25 pm 4:55 pm Aug 21 - Sep 1
2838 2:30 pm 5:00 pm Sep 3 - Sep 3
353 2:30 pm 5:00 pm Sep 10 - Sep 24
3112 3:10 pm 5:40 pm Aug 19 - Sep 23
5424 5:10 pm 7:40 pm Sep 10 - Sep 24
5424 5:10 pm 7:40 pm Aug 29 - Sep 29
5425 5:10 pm 7:40 pm Sep 3 - Sep 3
2829 5:35 pm 8:05 pm Sep 2 - Sep 2
2057 7:35 pm 10:00 pm Aug 19 - Sep 23
3434 8:05 pm 10:30 pm Sep 3 - Sep 3
3654 8:15 pm 10:40 pm Sep 10 - Sep 24
3731 8:45 pm 11:05 pm Sep 4 - Sep 4
6077 9:10 pm 11:30 pm Sep 9 - Sep 23
4328 9:55 pm 12:15 am Sep 3 - Sep 3
847 9:55 pm 12:15 am Aug 21 - Sep 1
847 9:55 pm 12:15 am Sep 5 - Sep 14
847 9:55 pm 12:15 am Sep 10 - Sep 17
847 9:55 pm 12:15 am Sep 24 - Sep 24
847 9:55 pm 12:15 am Sep 18 - Sep 29
* 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.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Houston
$184
Destination

Chicago
$184
Airlines