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Find Flight Deals from United States to Chicago Midway

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights to Chicago Midway

(Round-trip)
Depart: Fri Jan 9 2015 Return: Sun Jan 11 2015 Trip spans 3 days
Sun Country Air
Sun Country Air
MSP
3:15a
MDW
4:40a
1h 25m
nonstop
MDW
1:35p
MSP
3:00p
1h 25m
nonstop
Depart: Wed Jan 14 2015 Return: Sat Jan 17 2015 Trip spans 4 days
Frontier
Frontier
TTN
1:55a
MDW
4:15a
2h 20m
nonstop
MDW
12:35p
TTN
2:19p
1h 44m
nonstop
Depart: Tue Feb 10 2015 Return: Thu Feb 12 2015 Trip spans 3 days
Delta
Delta
BOS
9:28a
MDW
4:30p
7h 02m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Tue Apr 28 2015 Return: Tue May 5 2015 Trip spans 8 days
Delta
Delta
MIA
1:45p
MDW
6:27p
4h 42m
1 stop
MDW
2:00a
MIA
6:49a
4h 49m
1 stop
Depart: Sat May 23 2015 Return: Mon May 25 2015 Trip spans 3 days
Delta
Delta
CLE
3:00a
MDW
8:31a
5h 31m
1 stop
MDW
8:10a
CLE
1:12p
5h 02m
1 stop
Depart: Sun Jun 28 2015 Return: Tue Jun 30 2015 Trip spans 3 days
Delta
Delta
CMH
5:45a
MDW
10:12a
4h 27m
1 stop
MDW
7:05a
CMH
11:53a
4h 48m
1 stop
Depart: Tue Feb 24 2015 Return: Thu Feb 26 2015 Trip spans 3 days
Delta
Delta
DTW
10:36a
MDW
11:57a
1h 21m
nonstop
MDW
7:40a
DTW
8:48a
1h 08m
nonstop
Depart: Mon Apr 13 2015 Return: Fri Apr 17 2015 Trip spans 5 days
Delta
Delta
DFW
7:15a
MDW
1:50p
6h 35m
1 stop
MDW
3:15a
DFW
8:35a
5h 20m
1 stop
Depart: Mon Apr 20 2015 Return: Sat Apr 25 2015 Trip spans 6 days
Delta
Delta
EWR
7:00a
MDW
1:10p
6h 10m
1 stop
MDW
2:45a
EWR
8:52a
6h 07m
1 stop
Depart: Wed May 27 2015 Return: Sun May 31 2015 Trip spans 5 days
Delta
Delta
DAL
3:00a
MDW
10:42a
7h 42m
1 stop
MDW
2:00a
DAL
8:10a
6h 10m
1 stop
Depart: Wed May 6 2015 Return: Sun May 10 2015 Trip spans 5 days
Delta
Delta
OMA
3:10a
MDW
6:30a
3h 20m
1 stop
MDW
5:05a
OMA
10:25a
5h 20m
1 stop
Depart: Mon May 4 2015 Return: Fri May 8 2015 Trip spans 5 days
Delta
Delta
SFO
8:35p
MDW
2:33a
5h 58m
1 stop
MDW
2:45a
SFO
11:52a
9h 07m
1 stop
Depart: Sat Apr 11 2015 Return: Tue Apr 14 2015 Trip spans 4 days
Delta
Delta
ATL
12:15p
MDW
2:14p
1h 59m
nonstop
MDW
3:15a
ATL
5:06a
1h 51m
nonstop
Depart: Tue Jun 23 2015 Return: Sat Jul 4 2015 Trip spans 12 days
Delta
Delta
FLL
11:45a
MDW
4:54p
5h 09m
1 stop
MDW
12:45p
FLL
5:52p
5h 07m
1 stop
Depart: Sun Jun 14 2015 Return: Sun Jun 28 2015 Trip spans 15 days
Delta
Delta
MEM
4:30a
MDW
8:15a
3h 45m
1 stop
MDW
3:00a
MEM
7:06a
4h 06m
1 stop
Depart: Sun Apr 19 2015 Return: Fri Apr 24 2015 Trip spans 6 days
Delta
Delta
DEN
9:25a
MDW
3:53p
6h 28m
1 stop
MDW
2:00a
DEN
8:16a
6h 16m
1 stop
Depart: Sun Jun 21 2015 Return: Wed Jun 24 2015 Trip spans 4 days
Delta
Delta
PHL
2:00a
MDW
5:45a
3h 45m
1 stop
MDW
2:30p
PHL
6:20p
3h 50m
1 stop
Change your search
Airports
Origin

Detroit
$217
Fort Lauderdale
$252
Cleveland
$204
Miami
$184
Omaha
$245
San Francisco
$246
Minneapolis
$97
Atlanta
$247
Columbus
$210
Memphis
$257
Trenton
$105
Newark
$232
Denver
$312
Dallas
only $222
only $232
Philadelphia
$316
Boston
$184
Destination

Chicago
$97