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: Wed May 18 2016 Return: Tue May 24 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 52m
nonstop
ORD
HOU
2h 46m
nonstop
Depart: Tue Jul 19 2016 Return: Wed Jul 27 2016 Trip spans 9 days
Major Airline
Major Airline
HOU
ORD
2h 47m
nonstop
ORD
HOU
2h 44m
nonstop
Depart: Fri Jun 3 2016 Return: Tue Jun 7 2016 Trip spans 5 days
Southwest
Southwest
HOU
MDW
2h 20m
nonstop
MDW
HOU
2h 40m
nonstop
Depart: Tue Jun 28 2016 Return: Wed Jun 29 2016 Trip spans 2 days
Delta
Delta
HOU
MDW
5h 07m
1 stop
MDW
HOU
4h 40m
1 stop
Depart: Tue May 17 2016 Return: Wed May 18 2016 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 52m
nonstop
ORD
HOU
2h 54m
nonstop
Depart: Tue Jun 7 2016 Return: Wed Jun 8 2016 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 52m
nonstop
ORD
HOU
2h 46m
nonstop
Depart: Mon Jul 25 2016 Return: Thu Jul 28 2016 Trip spans 4 days
Major Airline
Major Airline
HOU
ORD
2h 50m
nonstop
ORD
HOU
2h 45m
nonstop
Depart: Tue Sep 6 2016 Return: Tue Sep 13 2016 Trip spans 8 days
Major Airline
Major Airline
HOU
ORD
2h 48m
nonstop
ORD
HOU
2h 45m
nonstop
Depart: Wed May 11 2016 Return: Mon May 16 2016 Trip spans 6 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 46m
nonstop
ORD
HOU
2h 54m
nonstop
Depart: Fri Oct 28 2016 Return: Sun Oct 30 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 36m
nonstop
ORD
HOU
2h 45m
nonstop
Depart: Sat Jun 4 2016 Return: Tue Jun 7 2016 Trip spans 4 days
Southwest
Southwest
HOU
MDW
2h 20m
nonstop
MDW
HOU
2h 35m
nonstop
Depart: Wed Jun 15 2016 Return: Wed Jun 22 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 46m
nonstop
ORD
HOU
2h 45m
nonstop
Depart: Mon Jun 20 2016 Return: Wed Jul 27 2016 Trip spans 38 days
Delta
Delta
HOU
MDW
5h 28m
1 stop
MDW
HOU
7h 19m
1 stop
Depart: Wed Jul 20 2016 Return: Wed Jul 27 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 55m
nonstop
ORD
HOU
2h 39m
nonstop
Depart: Fri Sep 9 2016 Return: Mon Sep 19 2016 Trip spans 11 days
Major Airline
Major Airline
HOU
MDW
7h 04m
1 stop
MDW
HOU
6h 05m
1 stop
Depart: Wed Nov 23 2016 Return: Sun Nov 27 2016 Trip spans 5 days
American Airlines
American Airlines
HOU
ORD
2h 58m
nonstop
ORD
HOU
2h 54m
nonstop
Depart: Tue Jul 26 2016 Return: Wed Jul 27 2016 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 55m
nonstop
ORD
HOU
2h 39m
nonstop
Depart: Wed Oct 19 2016 Return: Mon Oct 24 2016 Trip spans 6 days
Major Airline
Major Airline
HOU
MDW
4h 46m
1 stop
MDW
HOU
4h 58m
1 stop
Depart: Thu May 19 2016 Return: Fri May 20 2016 Trip spans 2 days
Southwest
Southwest
HOU
MDW
2h 20m
nonstop
MDW
HOU
2h 40m
nonstop
Depart: Fri Aug 26 2016 Return: Sun Aug 28 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
ORD
2h 55m
nonstop
ORD
HOU
2h 39m
nonstop
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 Jun 11 - Aug 6
322 6:00 am 8:25 am Jun 4 - Jun 4
322 6:00 am 8:25 am Apr 30 - May 21
322 6:15 am 8:40 am May 28 - May 28
5454 6:30 am 8:55 am Jun 5 - Jun 26
3487 6:50 am 9:25 am Jun 6 - Jul 1
1661 7:05 am 9:40 am May 31 - Jun 3
1661 7:05 am 9:40 am Apr 28 - May 27
2244 7:15 am 9:40 am May 28 - May 28
1158 7:20 am 9:45 am Jun 11 - Aug 6
1833 7:40 am 10:05 am Apr 30 - May 21
1833 7:40 am 10:05 am Jun 4 - Jun 4
3602 8:20 am 10:45 am Jun 5 - Jul 1
3107 9:30 am 11:55 am May 29 - May 29
3577 9:30 am 11:55 am May 1 - May 22
4054 9:30 am 11:55 am May 31 - Jun 3
4054 9:30 am 11:55 am Apr 28 - May 27
1097 12:10 pm 2:35 pm Jun 11 - Jul 30
622 2:05 pm 4:30 pm Jun 11 - Jun 25
622 2:05 pm 4:30 pm Jun 5 - Jul 1
3074 2:20 pm 4:40 pm Apr 30 - Jun 4
1372 2:25 pm 4:45 pm May 29 - May 29
3665 2:25 pm 4:45 pm May 30 - May 30
846 2:25 pm 4:45 pm Apr 28 - May 27
846 2:25 pm 4:45 pm May 31 - Jun 3
1078 3:30 pm 5:55 pm Jun 5 - Aug 5
4325 5:00 pm 7:20 pm May 28 - May 28
3739 5:10 pm 7:30 pm Jun 4 - Jun 4
3739 5:10 pm 7:30 pm Apr 30 - May 21
5234 6:05 pm 8:25 pm May 29 - May 29
5234 6:05 pm 8:25 pm May 30 - May 30
41 6:10 pm 8:30 pm Apr 28 - May 27
41 6:10 pm 8:30 pm May 31 - Jun 3
5144 6:10 pm 8:30 pm May 1 - May 22
2496 6:55 pm 9:20 pm Jun 5 - Jul 1
1181 8:05 pm 10:25 pm May 29 - May 29
836 8:05 pm 10:25 pm Apr 28 - May 20
836 8:05 pm 10:25 pm May 31 - Jun 3
836 8:05 pm 10:25 pm May 22 - May 27
6517 8:10 pm 10:30 pm May 30 - May 30
3974 9:15 pm 11:40 pm Jun 11 - Aug 6
1045 9:55 pm 12:15 am Jun 4 - Jun 4
1045 9:55 pm 12:15 am Apr 30 - May 21
1045 9:55 pm 12:15 am May 31 - Jun 3
1045 9:55 pm 12:15 am Apr 28 - May 27
4213 9:55 pm 12:15 am May 30 - May 30
4213 9:55 pm 12:15 am May 28 - May 28
2662 10:10 pm 12:35 am Jun 5 - Jul 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

We aggregate tons 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 don'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
$112
Destination

Chicago
only $112
only $166