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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
4:05a
MSP
5:30a
1h 25m
nonstop
Depart: Wed Jan 7 2015 Return: Tue Jan 13 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
DEN
1:00a
ORD
3:26a
2h 26m
nonstop
ORD
6:07a
DEN
8:49a
2h 42m
nonstop
Depart: Fri Jan 16 2015 Return: Wed Jan 21 2015 Trip spans 6 days
Frontier
Frontier
IAD
3:20a
ORD
5:25a
2h 05m
nonstop
ORD
7:50a
IAD
9:40a
1h 50m
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 Feb 5 2015 Return: Sun Feb 8 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 Feb 18 2015 Return: Sat Feb 21 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: Wed Jan 21 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
DFW
11:53a
ORD
2:12p
2h 19m
nonstop
ORD
1:45p
DFW
4:16p
2h 31m
nonstop
Depart: Wed Feb 4 2015 Return: Sat Feb 7 2015 Trip spans 4 days
Frontier
Frontier
ATL
6:05a
ORD
8:05a
2h 00m
nonstop
ORD
2:25a
ATL
4:20a
1h 55m
nonstop
Depart: Mon Feb 9 2015 Return: Tue Feb 17 2015 Trip spans 9 days
Spirit Airlines
Spirit Airlines
OAK
3:53a
ORD
8:00a
4h 07m
nonstop
ORD
10:53a
OAK
3:37p
4h 44m
nonstop
Depart: Tue Apr 21 2015 Return: Wed Apr 22 2015 Trip spans 2 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 May 5 2015 Return: Wed May 6 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
10:00a
ORD
12:43p
2h 43m
nonstop
ORD
9:38a
BOS
12:04p
2h 26m
nonstop
Depart: Sun May 24 2015 Return: Tue May 26 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
HOU
2:00a
ORD
4:38a
2h 38m
nonstop
ORD
5:25a
HOU
8:06a
2h 41m
nonstop
Depart: Wed Jun 3 2015 Return: Wed Jun 10 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
IAH
2:00a
ORD
4:38a
2h 38m
nonstop
ORD
3:00p
IAH
5:44p
2h 44m
nonstop
Depart: Tue Jun 23 2015 Return: Wed Jul 1 2015 Trip spans 9 days
Delta
Delta
MIA
5:00a
ORD
10:25a
5h 25m
1 stop
ORD
4:00a
MIA
11:49a
7h 49m
1 stop
Depart: Fri May 22 2015 Return: Mon May 25 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MSP
4:15a
MDW
5:40a
1h 25m
nonstop
MDW
6:30a
MSP
7:55a
1h 25m
nonstop
Depart: Thu Jun 11 2015 Return: Tue Jun 16 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
PDX
7:55p
ORD
11:53p
3h 58m
nonstop
ORD
4:35p
PDX
8:56p
4h 21m
nonstop
Depart: Fri Jun 26 2015 Return: Mon Jun 29 2015 Trip spans 4 days
Delta
Delta
EWR
7:00a
ORD
11:14a
4h 14m
1 stop
ORD
1:05p
EWR
6:01p
4h 56m
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: Sun Apr 26 2015 Return: Fri May 1 2015 Trip spans 6 days
Delta
Delta
SFO
3:30a
ORD
10:32a
7h 02m
1 stop
ORD
5:10a
SFO
11:52a
6h 42m
1 stop
Depart: Mon Apr 27 2015 Return: Tue May 5 2015 Trip spans 9 days
US Airways
US Airways
PHX
8:59p
ORD
12:22a
3h 23m
nonstop
ORD
6:10p
PHX
9:47p
3h 37m
nonstop
Change your search
Airports
Origin

Portland
$222
Oakland
$117
Washington
$92
Miami
$184
San Francisco
$246
Minneapolis
$81
Atlanta
$108
Orlando
$97
Phoenix
$247
Trenton
$105
Newark
$232
Denver
$81
Dallas
$107
Tampa
$97
Philadelphia
$157
Houston
only $175
only $175
Boston
$157
Destination

Chicago
only $81
only $105