Find Cheap Flights to Chicago

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: Wed Aug 23 2017 Return: Thu Aug 24 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 42m
nonstop
ORD
HOU
2h 42m
nonstop
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
American Airlines
American Airlines
HOU
ORD
2h 45m
nonstop
ORD
HOU
2h 46m
nonstop
Depart: Sat Jan 20 2018 Return: Tue Jan 30 2018 Trip spans 11 days
Multiple Airlines
Multiple Airlines
HOU
ORD
2h 40m
nonstop
ORD
HOU
3h 01m
nonstop
Depart: Sat Sep 2 2017 Return: Sat Sep 9 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 42m
nonstop
ORD
HOU
2h 40m
nonstop
Depart: Sat Dec 2 2017 Return: Tue Dec 5 2017 Trip spans 4 days
American Airlines
American Airlines
HOU
ORD
2h 45m
nonstop
ORD
HOU
2h 46m
nonstop
Depart: Wed Sep 20 2017 Return: Wed Sep 27 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 42m
nonstop
ORD
HOU
2h 48m
nonstop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Delta
Delta
HOU
MDW
5h 45m
1 stop
MDW
HOU
4h 51m
1 stop
Depart: Sun Oct 1 2017 Return: Fri Oct 27 2017 Trip spans 27 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 42m
nonstop
ORD
HOU
2h 40m
nonstop
Depart: Sat Sep 2 2017 Return: Mon Sep 4 2017 Trip spans 3 days
United
United
HOU
ORD
2h 53m
nonstop
ORD
HOU
2h 34m
nonstop
Depart: Wed Aug 23 2017 Return: Sat Aug 26 2017 Trip spans 4 days
American Airlines
American Airlines
HOU
ORD
2h 39m
nonstop
ORD
HOU
2h 45m
nonstop
Depart: Tue Oct 3 2017 Return: Sat Oct 7 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 41m
nonstop
ORD
HOU
2h 48m
nonstop
Depart: Sat Oct 14 2017 Return: Wed Oct 18 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 41m
nonstop
ORD
HOU
2h 46m
nonstop
Depart: Thu Nov 2 2017 Return: Mon Nov 6 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 42m
nonstop
ORD
HOU
2h 48m
nonstop
Depart: Mon Nov 20 2017 Return: Thu Nov 23 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
HOU
ORD
2h 45m
nonstop
ORD
HOU
2h 52m
nonstop
Depart: Thu Nov 2 2017 Return: Sat Nov 4 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 42m
nonstop
ORD
HOU
2h 40m
nonstop
Depart: Sat Sep 16 2017 Return: Tue Sep 19 2017 Trip spans 4 days
Delta
Delta
HOU
MDW
5h 10m
1 stop
MDW
HOU
6h 14m
1 stop
Depart: Fri Feb 2 2018 Return: Tue Feb 6 2018 Trip spans 5 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 35m
nonstop
ORD
HOU
2h 47m
nonstop
Depart: Mon Oct 2 2017 Return: Tue Oct 3 2017 Trip spans 2 days
Delta
Delta
HOU
MDW
5h 41m
1 stop
MDW
HOU
6h 44m
1 stop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Delta
Delta
HOU
MDW
8h 05m
1 stop
MDW
HOU
4h 47m
1 stop
Depart: Thu Nov 9 2017 Return: Mon Nov 13 2017 Trip spans 5 days
Delta
Delta
HOU
MDW
7h 49m
1 stop
MDW
HOU
7h 30m
1 stop
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
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.

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
$81
Destination

Chicago
only $81
only $184