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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: Thu Jan 8 2015 Return: Fri Jan 9 2015 Trip spans 2 days
Sun Country Air
Sun Country Air
MSP
11:20a
MDW
12:45p
1h 25m
nonstop
MDW
5:30a
MSP
6:55a
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 Apr 14 2015 Return: Mon Apr 27 2015 Trip spans 14 days
Delta
Delta
CMH
11:30a
MDW
2:50p
3h 20m
1 stop
MDW
2:30p
CMH
5:38p
3h 08m
1 stop
Depart: Sun Feb 1 2015 Return: Tue Feb 3 2015 Trip spans 3 days
Delta
Delta
BOS
7:31a
MDW
12:04p
4h 33m
1 stop
MDW
11:31a
BOS
4:09p
4h 38m
1 stop
Depart: Tue May 5 2015 Return: Tue May 12 2015 Trip spans 8 days
Delta
Delta
MIA
11:15a
MDW
4:54p
5h 39m
1 stop
MDW
2:00a
MIA
6:49a
4h 49m
1 stop
Depart: Tue Apr 7 2015 Return: Thu Apr 9 2015 Trip spans 3 days
Delta
Delta
CLE
9:45a
MDW
1:10p
3h 25m
1 stop
MDW
8:30a
CLE
1:07p
4h 37m
1 stop
Depart: Wed May 6 2015 Return: Wed May 13 2015 Trip spans 8 days
Delta
Delta
DTW
11:45a
MDW
1:10p
1h 25m
nonstop
MDW
3:00a
DTW
4:20a
1h 20m
nonstop
Depart: Wed Jun 17 2015 Return: Wed Jun 24 2015 Trip spans 8 days
Delta
Delta
DFW
7:15a
MDW
12:10p
4h 55m
1 stop
MDW
5:15a
DFW
10:12a
4h 57m
1 stop
Depart: Tue Feb 24 2015 Return: Thu Feb 26 2015 Trip spans 3 days
Delta
Delta
ATL
8:43a
MDW
10:39a
1h 56m
nonstop
MDW
4:46a
ATL
6:40a
1h 54m
nonstop
Depart: Tue Apr 28 2015 Return: Tue May 5 2015 Trip spans 8 days
Delta
Delta
OMA
5:20a
MDW
10:30a
5h 10m
1 stop
MDW
7:05a
OMA
10:25a
3h 20m
1 stop
Depart: Sat May 2 2015 Return: Tue May 5 2015 Trip spans 4 days
Delta
Delta
MEM
9:15a
MDW
1:24p
4h 09m
1 stop
MDW
9:50a
MEM
1:50p
4h 00m
1 stop
Depart: Mon Apr 6 2015 Return: Tue Apr 7 2015 Trip spans 2 days
Delta
Delta
EWR
2:30p
MDW
7:02p
4h 32m
1 stop
MDW
6:10a
EWR
11:10a
5h 00m
1 stop
Depart: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
Delta
Delta
SFO
2:40a
MDW
8:30a
5h 50m
1 stop
MDW
5:05a
SFO
11:52a
6h 47m
1 stop
Depart: Fri Jun 26 2015 Return: Tue Jun 30 2015 Trip spans 5 days
Delta
Delta
DAL
6:05a
MDW
10:42a
4h 37m
1 stop
MDW
6:10a
DAL
11:00a
4h 50m
1 stop
Depart: Mon Dec 29 2014 Return: Sun Jan 18 2015 Trip spans 21 days
Delta
Delta
PBI
12:50p
MDW
5:52p
5h 02m
1 stop
MDW
1:00a
PBI
5:48a
4h 48m
1 stop
Depart: Mon May 18 2015 Return: Tue May 19 2015 Trip spans 2 days
Delta
Delta
FLL
11:45a
MDW
4:54p
5h 09m
1 stop
MDW
5:15a
FLL
12:03p
6h 48m
1 stop
Depart: Sun May 24 2015 Return: Wed May 27 2015 Trip spans 4 days
Delta
Delta
BWI
2:15a
MDW
6:00a
3h 45m
1 stop
MDW
3:00a
BWI
6:58a
3h 58m
1 stop
Depart: Sun Jun 21 2015 Return: Sun Jun 28 2015 Trip spans 8 days
Delta
Delta
PHL
2:00a
MDW
5:45a
3h 45m
1 stop
MDW
2:30p
PHL
6:20p
3h 50m
1 stop
Depart: Sun Apr 5 2015 Return: Thu Apr 9 2015 Trip spans 5 days
Delta
Delta
IAD
8:45a
MDW
1:10p
4h 25m
1 stop
MDW
3:00a
IAD
6:46a
3h 46m
1 stop
Depart: Sun May 10 2015 Return: Sat May 16 2015 Trip spans 7 days
Delta
Delta
LAX
8:55a
MDW
2:53p
5h 58m
1 stop
MDW
1:10p
LAX
9:42p
8h 32m
1 stop
Change your search
Airports
Origin

Detroit
$201
Fort Lauderdale
$269
Cleveland
$188
Washington
$322
Miami
$184
Omaha
$225
West Palm Beach
$260
San Francisco
$246
Baltimore
$302
Minneapolis
$97
Atlanta
$225
Columbus
$182
Memphis
$225
Trenton
$105
Los Angeles
$336
Newark
$232
Dallas
only $222
only $252
Philadelphia
$316
Boston
$184
Destination

Chicago
$97