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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
1:16a
ORD
2:45a
1h 29m
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
1:00a
ORD
3:26a
2h 26m
nonstop
ORD
6:07a
DEN
8:49a
2h 42m
nonstop
Depart: Mon Jan 19 2015 Return: Tue Jan 20 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
DFW
1:16a
ORD
3:35a
2h 19m
nonstop
ORD
4:15a
DFW
6:46a
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: Wed Feb 11 2015 Return: Fri Feb 13 2015 Trip spans 3 days
Frontier
Frontier
IAD
1:55a
ORD
4:00a
2h 05m
nonstop
ORD
7:50a
IAD
9:40a
1h 50m
nonstop
Depart: Tue Mar 10 2015 Return: Wed Mar 18 2015 Trip spans 9 days
Frontier
Frontier
ATL
6:00a
ORD
8:00a
2h 00m
nonstop
ORD
3:30a
ATL
5:20a
1h 50m
nonstop
Depart: Tue Apr 14 2015 Return: Tue Apr 21 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
MCO
1:35p
ORD
4:37p
3h 02m
nonstop
ORD
6:52a
MCO
9:27a
2h 35m
nonstop
Depart: Tue May 5 2015 Return: Fri May 8 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
10:00a
ORD
12:43p
2h 43m
nonstop
ORD
9:38a
BOS
12:04p
2h 26m
nonstop
Depart: Tue May 19 2015 Return: Wed May 27 2015 Trip spans 9 days
Spirit Airlines
Spirit Airlines
PHL
2:05a
ORD
4:23a
2h 18m
nonstop
ORD
4:45p
PHL
6:41p
1h 56m
nonstop
Depart: Mon Dec 29 2014 Return: Wed Jan 28 2015 Trip spans 31 days
Spirit Airlines
Spirit Airlines
LGA
3:30a
ORD
6:08a
2h 38m
nonstop
ORD
12:59p
LGA
3:06p
2h 07m
nonstop
Depart: Tue Jun 9 2015 Return: Tue Jun 16 2015 Trip spans 8 days
Delta
Delta
MIA
7:40a
ORD
12:39p
4h 59m
1 stop
ORD
10:00a
MIA
2:29p
4h 29m
1 stop
Depart: Wed Jun 17 2015 Return: Tue Jun 23 2015 Trip spans 7 days
American Airlines
American Airlines
TPA
1:34p
ORD
4:30p
2h 56m
nonstop
ORD
4:45a
TPA
7:27a
2h 42m
nonstop
Depart: Tue Apr 28 2015 Return: Fri May 1 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BWI
4:55p
ORD
7:02p
2h 07m
nonstop
ORD
5:04p
BWI
6:59p
1h 55m
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: Tue Jun 16 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
PDX
7:55p
ORD
11:53p
3h 58m
nonstop
ORD
4:35p
PDX
8:56p
4h 21m
nonstop
Depart: Tue Jun 16 2015 Return: Wed Jun 17 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
HOU
2:00a
ORD
4:38a
2h 38m
nonstop
ORD
3:00p
HOU
5:44p
2h 44m
nonstop
Depart: Sun Apr 26 2015 Return: Mon Apr 27 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
SAN
9:50a
ORD
1:40p
3h 50m
nonstop
ORD
6:44a
SAN
10:59a
4h 15m
nonstop
Depart: Mon May 25 2015 Return: Fri May 29 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
DCA
2:00a
ORD
6:52a
4h 52m
1 stop
ORD
11:35a
DCA
5:33p
5h 58m
1 stop
Depart: Fri Jun 26 2015 Return: Sun Jun 28 2015 Trip spans 3 days
Delta
Delta
EWR
7:00a
ORD
11:14a
4h 14m
1 stop
ORD
12:25p
EWR
4:26p
4h 01m
1 stop
Change your search
Airports
Origin

Portland
$222
Oakland
$197
Washington
only $105
only $228
Miami
$184
New York City
$177
San Diego
$227
Baltimore
$197
Minneapolis
$81
Atlanta
$138
Orlando
$141
Newark
$232
Denver
$81
Dallas
$81
Tampa
$194
Philadelphia
$157
Houston
$225
Boston
$157
Destination

Chicago
only $81
only $97