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

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: Tue Jan 6 2015 Return: Wed Jan 7 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Thu Jan 8 2015 Return: Fri Jan 9 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Fri Jan 9 2015 Return: Mon Jan 12 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Sun Jan 11 2015 Return: Mon Jan 12 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Tue Jan 13 2015 Return: Sat Jan 17 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Wed Jan 14 2015 Return: Sat Jan 17 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Thu Jan 15 2015 Return: Mon Jan 19 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Sat Jan 17 2015 Return: Mon Jan 19 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Sun Jan 18 2015 Return: Mon Jan 19 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Tue Jan 20 2015 Return: Thu Jan 22 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Wed Jan 21 2015 Return: Thu Jan 22 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Thu Jan 22 2015 Return: Sat Jan 24 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Sun Jan 25 2015 Return: Mon Jan 26 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Sat Jan 31 2015 Return: Mon Feb 2 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Sun Feb 1 2015 Return: Mon Feb 2 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
1:15a
ORD
3:47a
2h 32m
nonstop
ORD
3:20p
HOU
6:07p
2h 47m
nonstop
Depart: Thu Dec 25 2014 Return: Tue Jan 6 2015 Trip spans 13 days
American Airlines
American Airlines
HOU
7:50a
ORD
10:25a
2h 35m
nonstop
ORD
8:05a
HOU
10:50a
2h 45m
nonstop
Depart: Sat Dec 27 2014 Return: Mon Dec 29 2014 Trip spans 3 days
US Airways
US Airways
HOU
2:00a
ORD
7:51a
5h 51m
1 stop
ORD
12:50a
HOU
8:03a
7h 13m
1 stop
Depart: Fri Jun 12 2015 Return: Tue Jun 16 2015 Trip spans 5 days
United
United
HOU
6:20a
ORD
8:53a
2h 33m
nonstop
ORD
8:00a
HOU
10:55a
2h 55m
nonstop
Depart: Thu Mar 26 2015 Return: Tue Apr 7 2015 Trip spans 13 days
Delta
Delta
HOU
6:05a
MDW
10:42a
4h 37m
1 stop
MDW
8:30a
HOU
4:09p
7h 39m
1 stop
Depart: Thu Apr 9 2015 Return: Thu Apr 16 2015 Trip spans 8 days
Delta
Delta
HOU
2:45a
ORD
8:05a
5h 20m
1 stop
ORD
8:45a
HOU
4:09p
7h 24m
1 stop
Change your search
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
1855 5:50 am 8:25 am Dec 29 - Jan 2
4891 5:55 am 8:30 am Jan 3 - Jan 3
577 5:55 am 8:30 am Jan 5 - Jan 5
1877 6:00 am 8:30 am Jan 4 - Jan 4
764 6:00 am 8:35 am Dec 20 - Dec 27
764 6:00 am 8:35 am Dec 26 - Dec 26
764 6:00 am 8:35 am Dec 28 - Dec 28
3573 6:35 am 9:00 am Jan 16 - Jan 26
3573 6:35 am 9:00 am Jan 6 - Jan 12
459 7:00 am 9:30 am Dec 26 - Dec 26
991 7:00 am 9:35 am Dec 20 - Dec 27
1653 7:10 am 9:45 am Dec 29 - Jan 5
1653 7:10 am 9:45 am Dec 31 - Dec 31
1916 7:10 am 9:45 am Jan 3 - Jan 3
430 7:10 am 9:35 am Jan 6 - Mar 6
752 7:15 am 9:45 am Jan 1 - Jan 1
614 7:30 am 9:55 am Jan 17 - Jan 24
2743 7:35 am 10:10 am Dec 28 - Dec 28
875 8:45 am 11:10 am Dec 28 - Dec 28
875 8:45 am 11:10 am Dec 20 - Dec 27
1022 8:55 am 11:20 am Jan 3 - Jan 3
2647 8:55 am 11:20 am Dec 31 - Dec 31
401 8:55 am 11:20 am Jan 4 - Jan 4
3662 9:00 am 11:25 am Dec 26 - Dec 26
3 9:10 am 11:35 am Jan 5 - Jan 5
4463 9:10 am 11:35 am Dec 29 - Jan 2
3884 9:35 am 12:00 pm Jan 10 - Feb 28
1531 10:00 am 12:30 pm Dec 29 - Jan 5
1531 10:00 am 12:30 pm Jan 4 - Jan 4
527 11:10 am 1:35 pm Jan 11 - Mar 1
527 11:10 am 1:35 pm Jan 6 - Mar 6
846 12:25 pm 2:50 pm Dec 25 - Dec 25
1007 12:35 pm 3:00 pm Dec 26 - Dec 26
3184 12:35 pm 3:00 pm Dec 20 - Dec 27
3184 12:35 pm 3:00 pm Dec 28 - Dec 28
2688 1:25 pm 3:50 pm Dec 31 - Dec 31
173 1:40 pm 4:05 pm Jan 3 - Jan 3
1850 1:40 pm 4:05 pm Jan 4 - Jan 4
1867 1:40 pm 4:05 pm Dec 29 - Jan 5
2400 1:40 pm 4:05 pm Jan 1 - Jan 1
3899 2:00 pm 4:25 pm Jan 10 - Feb 28
2505 3:00 pm 5:25 pm Jan 6 - Mar 6
521 3:35 pm 6:00 pm Dec 26 - Dec 28
2094 4:10 pm 6:35 pm Dec 25 - Dec 25
3736 4:40 pm 7:10 pm Jan 10 - Feb 28
151 5:15 pm 7:40 pm Jan 5 - Jan 5
1950 5:15 pm 7:40 pm Dec 31 - Dec 31
3225 5:15 pm 7:40 pm Dec 29 - Jan 4
2289 5:30 pm 7:55 pm Jan 1 - Jan 1
2259 6:00 pm 8:25 pm Dec 28 - Dec 28
2259 6:00 pm 8:25 pm Dec 20 - Dec 27
1456 6:40 pm 9:05 pm Jan 11 - Mar 1
43 6:40 pm 9:05 pm Jan 6 - Mar 6
742 6:55 pm 9:20 pm Dec 26 - Dec 26
407 7:20 pm 9:40 pm Jan 5 - Jan 5
1552 7:55 pm 10:15 pm Jan 3 - Jan 4
584 8:00 pm 10:20 pm Dec 29 - Jan 2
2385 8:10 pm 10:30 pm Dec 28 - Dec 28
2385 8:10 pm 10:30 pm Dec 20 - Dec 27
3306 8:15 pm 10:35 pm Dec 26 - Dec 26
411 9:00 pm 11:20 pm Jan 19 - Jan 23
411 9:00 pm 11:20 pm Jan 6 - Jan 8
1769 9:25 pm 11:50 pm Dec 25 - Dec 25
Airports
Origin

Houston
$155
Destination

Chicago
only $155
only $298