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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 Dec 25 2014 Return: Wed Dec 31 2014 Trip spans 7 days
Spirit Airlines
Spirit Airlines
MSP
1:50p
ORD
3:22p
1h 32m
nonstop
ORD
2:48p
MSP
4:14p
1h 26m
nonstop
Depart: Thu Jan 29 2015 Return: Sat Jan 31 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
DEN
1:00a
ORD
3:26a
2h 26m
nonstop
ORD
4:40p
DEN
7:22p
2h 42m
nonstop
Depart: Thu Jan 8 2015 Return: Sun Jan 11 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
TPA
6:13a
ORD
9:00a
2h 47m
nonstop
ORD
1:50a
TPA
4:33a
2h 43m
nonstop
Depart: Wed Jan 14 2015 Return: Tue Jan 20 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
MCO
12:40p
ORD
3:38p
2h 58m
nonstop
ORD
5:06a
MCO
7:43a
2h 37m
nonstop
Depart: Thu Jan 15 2015 Return: Sun Jan 18 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MSP
11:20a
MDW
12:45p
1h 25m
nonstop
MDW
1:35p
MSP
3:00p
1h 25m
nonstop
Depart: Wed Jan 7 2015 Return: Fri Jan 9 2015 Trip spans 3 days
Frontier
Frontier
IAD
3:20a
ORD
5:25a
2h 05m
nonstop
ORD
7:50a
IAD
9:40a
1h 50m
nonstop
Depart: Wed Feb 11 2015 Return: Sat Feb 14 2015 Trip spans 4 days
Frontier
Frontier
TTN
1:55a
MDW
4:15a
2h 20m
nonstop
MDW
12:35p
TTN
2:20p
1h 45m
nonstop
Depart: Tue Jan 20 2015 Return: Sat Jan 24 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
DFW
11:53a
ORD
2:12p
2h 19m
nonstop
ORD
1:45p
DFW
4:16p
2h 31m
nonstop
Depart: Sun Dec 28 2014 Return: Sat Jan 17 2015 Trip spans 21 days
Spirit Airlines
Spirit Airlines
ATL
4:26a
ORD
6:25a
1h 59m
nonstop
ORD
5:44a
ATL
7:34a
1h 50m
nonstop
Depart: Wed Dec 31 2014 Return: Thu Jan 1 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
LGA
3:30a
ORD
6:08a
2h 38m
nonstop
ORD
12:56a
LGA
3:00a
2h 04m
nonstop
Depart: Tue May 26 2015 Return: Sat May 30 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
10:00a
ORD
12:43p
2h 43m
nonstop
ORD
9:38a
BOS
12:04p
2h 26m
nonstop
Depart: Sat May 9 2015 Return: Tue May 12 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: Sun Mar 22 2015 Return: Thu Mar 26 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
HOU
2:16a
ORD
4:51a
2h 35m
nonstop
ORD
4:17p
HOU
7:00p
2h 43m
nonstop
Depart: Sun Apr 26 2015 Return: Sat May 2 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BWI
2:30a
ORD
4:32a
2h 02m
nonstop
ORD
4:05a
BWI
5:57a
1h 52m
nonstop
Depart: Fri Jun 19 2015 Return: Tue Jun 23 2015 Trip spans 5 days
Delta
Delta
EWR
7:00a
ORD
1:22p
6h 22m
1 stop
ORD
2:55a
EWR
8:50a
5h 55m
1 stop
Depart: Mon Jun 29 2015 Return: Tue Jul 7 2015 Trip spans 9 days
Delta
Delta
EWR
5:15a
MDW
9:15a
4h 00m
1 stop
MDW
2:30p
EWR
6:26p
3h 56m
1 stop
Depart: Tue Jun 23 2015 Return: Tue Jun 30 2015 Trip spans 8 days
Delta
Delta
JFK
2:45a
ORD
5:15a
2h 30m
nonstop
ORD
2:40p
JFK
4:53p
2h 13m
nonstop
Depart: Sun May 31 2015 Return: Tue Jun 2 2015 Trip spans 3 days
Delta
Delta
SFO
8:35p
ORD
4:32a
7h 57m
1 stop
ORD
8:05a
SFO
2:28p
6h 23m
1 stop
Depart: Sun Jun 28 2015 Return: Sat Jul 4 2015 Trip spans 7 days
Delta
Delta
SFO
8:35p
MDW
2:33a
5h 58m
1 stop
MDW
8:10a
SFO
2:28p
6h 18m
1 stop
Change your search
Airports
Origin

Washington
$105
New York City
only $235
only $137
San Francisco
$246
Baltimore
$197
Minneapolis
$81
Atlanta
$137
Orlando
$97
Trenton
$105
Newark
$232
Denver
$81
Dallas
$107
Tampa
$97
Philadelphia
$167
Houston
$175
Boston
$157
Destination

Chicago
only $81
only $97