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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
4:05a
MSP
5:30a
1h 25m
nonstop
Depart: Wed Jan 7 2015 Return: Thu Jan 8 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
DEN
8:40a
ORD
11:09a
2h 29m
nonstop
ORD
4:40p
DEN
7:22p
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 18 2015 Return: Mon Feb 23 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
TPA
9:20a
ORD
12:12p
2h 52m
nonstop
ORD
3:35a
TPA
6:16a
2h 41m
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: Sat Feb 28 2015 Return: Wed Mar 4 2015 Trip spans 5 days
Frontier
Frontier
TTN
4:30a
MDW
6:50a
2h 20m
nonstop
MDW
12:30p
TTN
2:19p
1h 49m
nonstop
Depart: Tue Mar 3 2015 Return: Thu Mar 5 2015 Trip spans 3 days
Frontier
Frontier
ATL
5:00a
ORD
7:00a
2h 00m
nonstop
ORD
2:30a
ATL
4:20a
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: Sun Apr 26 2015 Return: Tue Apr 28 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: Mon Feb 16 2015 Return: Mon Feb 23 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
HOU
1:20a
ORD
3:55a
2h 35m
nonstop
ORD
3:17p
HOU
6:00p
2h 43m
nonstop
Depart: Sun Dec 28 2014 Return: Sat Jan 10 2015 Trip spans 14 days
Spirit Airlines
Spirit Airlines
LGA
3:30a
ORD
6:08a
2h 38m
nonstop
ORD
12:53a
LGA
3:00a
2h 07m
nonstop
Depart: Wed May 27 2015 Return: Fri Jun 5 2015 Trip spans 10 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: Tue May 5 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
4:35a
ORD
8:42a
4h 07m
nonstop
ORD
10:35a
OAK
3:12p
4h 37m
nonstop
Depart: Mon May 18 2015 Return: Wed May 20 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
IAH
2:30p
ORD
5:05p
2h 35m
nonstop
ORD
3:00p
IAH
5:44p
2h 44m
nonstop
Depart: Sun May 24 2015 Return: Tue May 26 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
Depart: Mon Jun 29 2015 Return: Wed Jul 29 2015 Trip spans 31 days
JetBlue Airways
JetBlue Airways
DCA
2:00a
ORD
6:46a
4h 46m
1 stop
ORD
3:00a
DCA
7:44a
4h 44m
1 stop
Depart: Fri Jun 26 2015 Return: Mon Jun 29 2015 Trip spans 4 days
Delta
Delta
EWR
7:00a
ORD
1:22p
6h 22m
1 stop
ORD
1:05p
EWR
6:01p
4h 56m
1 stop
Depart: Fri Jun 19 2015 Return: Mon Jun 29 2015 Trip spans 11 days
Delta
Delta
SFO
8:35p
MDW
5:31a
8h 56m
1 stop
MDW
3:30p
SFO
10:03p
6h 33m
1 stop
Change your search
Airports
Origin

Portland
$207
Oakland
$187
Washington
only $105
only $228
New York City
$177
San Francisco
$246
Minneapolis
$81
Atlanta
$138
Orlando
$141
Trenton
$105
Newark
$232
Denver
$81
Dallas
$81
Tampa
$97
Philadelphia
$177
Houston
only $195
only $175
Boston
$157
Destination

Chicago
only $81
only $97