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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: 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 Feb 13 2015 Return: Sat Feb 14 2015 Trip spans 2 days
Frontier
Frontier
IAD
3:30a
ORD
5:35a
2h 05m
nonstop
ORD
7:50a
IAD
9:40a
1h 50m
nonstop
Depart: Tue Feb 10 2015 Return: Tue Feb 17 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
3:53a
ORD
8:00a
4h 07m
nonstop
ORD
10:53a
OAK
3:37p
4h 44m
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: Tue Jun 9 2015 Return: Tue Jun 16 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
MCO
1:16p
ORD
4:12p
2h 56m
nonstop
ORD
6:52a
MCO
9:27a
2h 35m
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 Apr 12 2015 Return: Sun Apr 19 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
DFW
2:16a
ORD
4:35a
2h 19m
nonstop
ORD
4:00p
DFW
6:21p
2h 21m
nonstop
Depart: Mon Apr 27 2015 Return: Wed May 13 2015 Trip spans 17 days
Multiple Airlines
Multiple Airlines
TPA
1:34p
ORD
4:30p
2h 56m
nonstop
ORD
10:15a
TPA
12:50p
2h 35m
nonstop
Depart: Mon May 11 2015 Return: Tue May 19 2015 Trip spans 9 days
Spirit Airlines
Spirit Airlines
BWI
4:55p
ORD
7:02p
2h 07m
nonstop
ORD
5:04p
BWI
6:59p
1h 55m
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: Sun Jun 21 2015 Return: Wed Jun 24 2015 Trip spans 4 days
Delta
Delta
EWR
7:00a
ORD
11:14a
4h 14m
1 stop
ORD
6:50a
EWR
12:25p
5h 35m
1 stop
Depart: Sun May 31 2015 Return: Sat Jun 13 2015 Trip spans 14 days
Delta
Delta
SFO
8:35p
MDW
5:31a
8h 56m
1 stop
MDW
1:10p
SFO
10:03p
8h 53m
1 stop
Depart: Sun Jun 14 2015 Return: Sun Jun 21 2015 Trip spans 8 days
Delta
Delta
ATL
8:15a
MDW
10:12a
1h 57m
nonstop
MDW
3:15a
ATL
5:06a
1h 51m
nonstop
Change your search
Airports
Origin

Oakland
$117
Washington
$105
New York City
$137
San Francisco
$246
Baltimore
$197
Minneapolis
$81
Atlanta
$257
Orlando
$146
Newark
$232
Denver
$81
Dallas
$177
Tampa
$183
Philadelphia
$167
Houston
$175
Boston
$157
Destination

Chicago
only $81
only $97