Find Deals on Flights from Houston Hobby & other airports to Chicago (HOU - CHI)

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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Houston Hobby & other airports to Chicago

(Round-trip)
Depart: Sat Sep 24 2016 Return: Mon Sep 26 2016 Trip spans 3 days
Depart: Wed Aug 17 2016 Return: Sat Aug 20 2016 Trip spans 4 days
Depart: Mon Aug 29 2016 Return: Tue Aug 30 2016 Trip spans 2 days
Depart: Wed Sep 28 2016 Return: Sat Oct 1 2016 Trip spans 4 days
Depart: Wed Oct 19 2016 Return: Mon Oct 24 2016 Trip spans 6 days
Depart: Tue Nov 29 2016 Return: Tue Dec 6 2016 Trip spans 8 days
Depart: Fri Oct 28 2016 Return: Mon Oct 31 2016 Trip spans 4 days
Depart: Thu Dec 1 2016 Return: Sun Dec 4 2016 Trip spans 4 days
Depart: Sat Sep 17 2016 Return: Wed Sep 21 2016 Trip spans 5 days
Depart: Thu Aug 18 2016 Return: Thu Aug 25 2016 Trip spans 8 days
Depart: Thu Oct 6 2016 Return: Mon Oct 10 2016 Trip spans 5 days
Depart: Sat Sep 24 2016 Return: Sun Sep 25 2016 Trip spans 2 days
Depart: Fri Oct 21 2016 Return: Sat Oct 22 2016 Trip spans 2 days
Depart: Fri Nov 4 2016 Return: Sat Nov 5 2016 Trip spans 2 days
Depart: Sat Aug 20 2016 Return: Mon Aug 29 2016 Trip spans 10 days
Depart: Sat Jul 30 2016 Return: Tue Aug 23 2016 Trip spans 25 days
Depart: Tue Aug 23 2016 Return: Sat Sep 3 2016 Trip spans 12 days
Depart: Thu Jan 12 2017 Return: Tue Jan 17 2017 Trip spans 6 days
Depart: Fri Aug 26 2016 Return: Mon Aug 29 2016 Trip spans 4 days
Depart: Fri Sep 9 2016 Return: Tue Sep 13 2016 Trip spans 5 days
Select an airline:  Southwest
Direct flights HOU to CHI on Southwest
Flight # Depart HOU Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
5564 5:25 am 7:50 am Jul 30 - Aug 6
2917 6:10 am 8:40 am Aug 8 - Sep 2
3487 6:50 am 9:25 am Jul 26 - Aug 5
6007 6:55 am 9:30 am Aug 7 - Aug 28
2170 7:05 am 9:40 am Aug 13 - Aug 27
4097 7:15 am 9:50 am Sep 3 - Sep 3
1158 7:20 am 9:45 am Jul 30 - Aug 6
1269 7:55 am 10:30 am Sep 4 - Sep 5
613 8:10 am 10:40 am Aug 7 - Sep 2
3602 8:20 am 10:45 am Jul 26 - Aug 5
1171 9:00 am 11:30 am Sep 3 - Sep 3
865 9:00 am 11:30 am Aug 13 - Aug 27
259 9:45 am 12:15 pm Aug 7 - Sep 2
4445 10:55 am 1:25 pm Sep 4 - Sep 4
3743 11:20 am 1:50 pm Aug 13 - Aug 27
1097 12:10 pm 2:35 pm Aug 6 - Aug 6
3494 1:40 pm 4:10 pm Sep 3 - Sep 3
622 2:05 pm 4:30 pm Jul 26 - Aug 5
622 2:05 pm 4:30 pm Jul 30 - Aug 6
2525 2:10 pm 4:40 pm Sep 4 - Sep 4
2867 2:10 pm 4:40 pm Aug 7 - Sep 2
3494 2:25 pm 4:55 pm Aug 13 - Aug 27
1078 3:30 pm 5:55 pm Jul 26 - Aug 5
1637 5:25 pm 7:55 pm Sep 3 - Sep 3
2336 5:40 pm 8:00 pm Aug 7 - Sep 2
5267 5:55 pm 8:15 pm Sep 4 - Sep 4
2496 6:55 pm 9:20 pm Jul 26 - Aug 5
3792 8:05 pm 10:25 pm Aug 13 - Aug 27
4830 8:10 pm 10:30 pm Sep 3 - Sep 3
3974 9:15 pm 11:40 pm Jul 30 - Aug 6
3045 9:55 pm 12:20 am Aug 7 - Oct 30
2662 10:10 pm 12:35 am Jul 26 - Aug 5
* 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.

We compile tonnes of data for you
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Houston
$75
Destination

Chicago
only $75
only $149