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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
4:05a
MSP
5:30a
1h 25m
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: Sat Feb 7 2015 Return: Tue Feb 10 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
DFW
1:16a
ORD
3:35a
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: Mon Feb 23 2015 Return: Wed Feb 25 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 Feb 24 2015 Return: Wed Feb 25 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
LGA
3:30a
ORD
6:05a
2h 35m
nonstop
ORD
12:59p
LGA
3:07p
2h 08m
nonstop
Depart: Tue Mar 10 2015 Return: Tue Mar 24 2015 Trip spans 15 days
Frontier
Frontier
ATL
6:00a
ORD
8:00a
2h 00m
nonstop
ORD
2:25a
ATL
4:15a
1h 50m
nonstop
Depart: Tue Mar 31 2015 Return: Tue Apr 7 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
MCO
1:35p
ORD
4:37p
3h 02m
nonstop
ORD
6:06a
MCO
8:41a
2h 35m
nonstop
Depart: Fri Jan 2 2015 Return: Sat Jan 10 2015 Trip spans 9 days
JetBlue Airways
JetBlue Airways
BOS
2:15a
ORD
5:17a
3h 02m
nonstop
ORD
9:30a
BOS
11:42a
2h 12m
nonstop
Depart: Sat Jun 6 2015 Return: Wed Jun 10 2015 Trip spans 5 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: Tue Jun 2 2015 Return: Tue Jun 9 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: 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: 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: 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 28 2015 Return: Tue Jun 30 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
JFK
2:30a
ORD
4:58a
2h 28m
nonstop
ORD
4:25p
JFK
6:37p
2h 12m
nonstop
Depart: Mon Jun 29 2015 Return: Mon Jul 6 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
TPA
6:30a
ORD
9:19a
2h 49m
nonstop
ORD
11:25a
TPA
2:02p
2h 37m
nonstop
Change your search
Airports
Origin

Portland
$222
Oakland
$187
Washington
$105
New York City
only $249
only $137
San Diego
$227
Minneapolis
$81
Atlanta
$138
Orlando
$141
Newark
$232
Denver
$81
Dallas
$81
Tampa
$257
Philadelphia
$167
Houston
$175
Boston
$155
Destination

Chicago
only $81
only $97