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Find Flight Deals from United States to Chicago

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

Book cheap flights to Chicago

(Round-trip)
Depart: Thu Jan 1 2015 Return: Wed Jan 7 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
MSP
1:50p
ORD
3:22p
1h 32m
nonstop
ORD
2:52p
MSP
4:19p
1h 27m
nonstop
Depart: Wed Jan 7 2015 Return: Sat Jan 10 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
DEN
8:40a
ORD
11:09a
2h 29m
nonstop
ORD
4:40p
DEN
7:22p
2h 42m
nonstop
Depart: Tue Feb 10 2015 Return: Wed Feb 11 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
DFW
11:53a
ORD
2:12p
2h 19m
nonstop
ORD
1:45p
DFW
4:16p
2h 31m
nonstop
Depart: Fri Jan 16 2015 Return: Sun Jan 18 2015 Trip spans 3 days
Sun Country Air
Sun Country Air
MSP
2:40a
MDW
4:05a
1h 25m
nonstop
MDW
1:35p
MSP
3:00p
1h 25m
nonstop
Depart: Fri Mar 6 2015 Return: Mon Mar 9 2015 Trip spans 3 days
Frontier
Frontier
IAD
3:30a
ORD
5:35a
2h 05m
nonstop
ORD
8:50a
IAD
10:40a
1h 50m
nonstop
Depart: Wed Dec 31 2014 Return: Wed Jan 7 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
LGA
4:55p
ORD
7:22p
2h 27m
nonstop
ORD
12:59p
LGA
3:06p
2h 07m
nonstop
Depart: Sat May 23 2015 Return: Tue May 26 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
MCO
1:16p
ORD
4:12p
2h 56m
nonstop
ORD
6:52a
MCO
9:27a
2h 35m
nonstop
Depart: Tue Dec 30 2014 Return: Tue Jan 13 2015 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ATL
4:26a
ORD
6:25a
1h 59m
nonstop
ORD
5:44a
ATL
7:34a
1h 50m
nonstop
Depart: Sat May 30 2015 Return: Mon Jun 1 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
10:00a
ORD
12:43p
2h 43m
nonstop
ORD
9:38a
BOS
12:04p
2h 26m
nonstop
Depart: Wed May 6 2015 Return: Sat May 9 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
PHL
2:05a
ORD
4:23a
2h 18m
nonstop
ORD
4:45p
PHL
6:41p
1h 56m
nonstop
Depart: Tue Apr 28 2015 Return: Mon May 4 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
HOU
2:30p
ORD
5:05p
2h 35m
nonstop
ORD
5:25a
HOU
8:06a
2h 41m
nonstop
Depart: Sun May 31 2015 Return: Tue Jun 9 2015 Trip spans 10 days
Spirit Airlines
Spirit Airlines
OAK
4:35a
ORD
8:42a
4h 07m
nonstop
ORD
10:35a
OAK
3:12p
4h 37m
nonstop
Depart: Wed Jun 24 2015 Return: Mon Jun 29 2015 Trip spans 6 days
Delta
Delta
BOS
6:30a
MDW
1:10p
6h 40m
1 stop
MDW
2:30p
BOS
6:32p
4h 02m
1 stop
Depart: Mon Jun 15 2015 Return: Wed Jul 1 2015 Trip spans 17 days
Spirit Airlines
Spirit Airlines
TPA
6:30a
ORD
9:21a
2h 51m
nonstop
ORD
11:25a
TPA
2:02p
2h 37m
nonstop
Depart: Sun Jun 21 2015 Return: Thu Jun 25 2015 Trip spans 5 days
Delta
Delta
EWR
7:00a
ORD
11:14a
4h 14m
1 stop
ORD
9:15a
EWR
1:00p
3h 45m
1 stop
Depart: Sun Jun 14 2015 Return: Tue Jun 16 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
PDX
7:55p
ORD
11:53p
3h 58m
nonstop
ORD
4:35p
PDX
8:56p
4h 21m
nonstop
Change your search
Airports
Origin

Portland
$252
Oakland
$197
Washington
$105
New York City
$137
Minneapolis
$81
Atlanta
$147
Orlando
$146
Newark
$232
Denver
$81
Dallas
$94
Tampa
$212
Philadelphia
$167
Houston
$175
Boston
$157
Destination

Chicago
only $81
only $97