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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: Mon Mar 9 2015 Return: Thu Mar 12 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MSP
3:10a
MDW
4:35a
1h 25m
nonstop
MDW
2:35p
MSP
4:00p
1h 25m
nonstop
Depart: Wed Mar 18 2015 Return: Mon Mar 23 2015 Trip spans 6 days
Frontier
Frontier
TTN
2:55a
MDW
5:03a
2h 08m
nonstop
MDW
4:15a
TTN
6:03a
1h 48m
nonstop
Depart: Wed Mar 4 2015 Return: Tue Mar 10 2015 Trip spans 6 days
Delta
Delta
HOU
7:40a
MDW
12:22p
4h 42m
1 stop
MDW
11:37a
HOU
5:50p
6h 13m
1 stop
Depart: Tue May 12 2015 Return: Tue May 19 2015 Trip spans 8 days
Delta
Delta
IAH
4:30a
MDW
9:12a
4h 42m
1 stop
MDW
8:30a
IAH
1:19p
4h 49m
1 stop
Depart: Tue Mar 10 2015 Return: Wed Mar 11 2015 Trip spans 2 days
Delta
Delta
MSY
6:15a
MDW
1:22p
7h 07m
1 stop
MDW
10:11a
MSY
2:35p
4h 24m
1 stop
Depart: Fri Mar 13 2015 Return: Mon Mar 16 2015 Trip spans 4 days
Delta
Delta
DCA
2:00a
MDW
5:45a
3h 45m
1 stop
MDW
12:34p
DCA
6:06p
5h 32m
1 stop
Depart: Mon Apr 27 2015 Return: Mon May 4 2015 Trip spans 8 days
Delta
Delta
BOS
2:50p
MDW
6:45p
3h 55m
1 stop
MDW
2:30p
BOS
6:32p
4h 02m
1 stop
Depart: Sat Jul 18 2015 Return: Thu Jul 23 2015 Trip spans 6 days
Delta
Delta
FLL
4:00a
MDW
9:15a
5h 15m
1 stop
MDW
3:15a
FLL
9:55a
6h 40m
1 stop
Depart: Sat Aug 1 2015 Return: Thu Aug 6 2015 Trip spans 6 days
Delta
Delta
PBI
1:45p
MDW
6:32p
4h 47m
1 stop
MDW
2:00a
PBI
6:45a
4h 45m
1 stop
Depart: Tue Aug 11 2015 Return: Mon Aug 17 2015 Trip spans 7 days
Delta
Delta
TPA
6:45a
MDW
11:42a
4h 57m
1 stop
MDW
1:55p
TPA
7:25p
5h 30m
1 stop
Depart: Sun Mar 8 2015 Return: Tue Mar 10 2015 Trip spans 2 days
Delta
Delta
JFK
1:15a
MDW
8:46a
6h 31m
1 stop
MDW
5:51a
JFK
1:20p
7h 29m
1 stop
Depart: Mon Aug 17 2015 Return: Wed Aug 19 2015 Trip spans 3 days
Delta
Delta
DTW
1:25p
MDW
2:50p
1h 25m
nonstop
MDW
2:30p
DTW
3:50p
1h 20m
nonstop
Depart: Mon Jul 20 2015 Return: Wed Jul 22 2015 Trip spans 3 days
Delta
Delta
CMH
1:20p
MDW
5:53p
4h 33m
1 stop
MDW
2:00a
CMH
6:35a
4h 35m
1 stop
Depart: Tue Jul 21 2015 Return: Mon Aug 3 2015 Trip spans 14 days
Delta
Delta
OMA
9:10a
MDW
2:47p
5h 37m
1 stop
MDW
7:05a
OMA
10:25a
3h 20m
1 stop
Depart: Sun Aug 16 2015 Return: Fri Aug 21 2015 Trip spans 6 days
Delta
Delta
CLT
4:15a
MDW
8:49a
4h 34m
1 stop
MDW
3:15a
CLT
7:32a
4h 17m
1 stop
Depart: Mon Jul 27 2015 Return: Fri Jul 31 2015 Trip spans 5 days
Delta
Delta
ATL
12:15p
MDW
2:14p
1h 59m
nonstop
MDW
3:15a
ATL
5:06a
1h 51m
nonstop
Change your search
Airports
Origin

New York
$215
Detroit
$219
Charlotte
$256
Fort Lauderdale
$184
Washington
$184
Omaha
$235
West Palm Beach
$184
Minneapolis
$81
Atlanta
$267
New Orleans
$184
Columbus
$220
Trenton
$105
Tampa
$184
Houston
only $182
only $182
Boston
$184
Destination

Chicago
$81