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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 15 2015 Return: Sun Jan 18 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MSP
11:20a
MDW
12:45p
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 Apr 21 2015 Return: Tue Apr 28 2015 Trip spans 8 days
Delta
Delta
CMH
3:15a
MDW
8:49a
5h 34m
1 stop
MDW
3:00a
CMH
5:59a
2h 59m
1 stop
Depart: Tue Mar 10 2015 Return: Tue Mar 17 2015 Trip spans 8 days
Delta
Delta
BOS
10:43a
MDW
2:50p
4h 07m
1 stop
MDW
5:00a
BOS
9:02a
4h 02m
1 stop
Depart: Wed May 20 2015 Return: Tue May 26 2015 Trip spans 7 days
Delta
Delta
MIA
5:00a
MDW
10:12a
5h 12m
1 stop
MDW
9:50a
MIA
2:29p
4h 39m
1 stop
Depart: Mon Mar 9 2015 Return: Sat Mar 14 2015 Trip spans 6 days
Delta
Delta
DTW
4:05a
MDW
5:30a
1h 25m
nonstop
MDW
8:40a
DTW
9:50a
1h 10m
nonstop
Depart: Fri Dec 26 2014 Return: Tue Jan 6 2015 Trip spans 12 days
Frontier
Frontier
DEN
9:50a
MDW
12:03p
2h 13m
nonstop
MDW
1:45p
DEN
4:23p
2h 38m
nonstop
Depart: Wed Apr 8 2015 Return: Mon Apr 13 2015 Trip spans 6 days
Delta
Delta
DFW
8:00a
MDW
12:51p
4h 51m
1 stop
MDW
11:27a
DFW
5:25p
5h 58m
1 stop
Depart: Tue May 5 2015 Return: Sun May 10 2015 Trip spans 6 days
Delta
Delta
DAL
3:00a
MDW
9:12a
6h 12m
1 stop
MDW
3:15a
DAL
8:10a
4h 55m
1 stop
Depart: Mon Mar 2 2015 Return: Mon Mar 9 2015 Trip spans 7 days
Delta
Delta
ATL
3:30p
MDW
5:27p
1h 57m
nonstop
MDW
8:30a
ATL
10:20a
1h 50m
nonstop
Depart: Sat Apr 25 2015 Return: Sat May 23 2015 Trip spans 29 days
Delta
Delta
OMA
3:10a
MDW
6:30a
3h 20m
1 stop
MDW
11:10a
OMA
4:38p
5h 28m
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: Wed Apr 22 2015 Return: Sun Apr 26 2015 Trip spans 5 days
Delta
Delta
SFO
8:35p
MDW
2:33a
5h 58m
1 stop
MDW
8:10a
SFO
5:41p
9h 31m
1 stop
Depart: Sun May 10 2015 Return: Wed May 13 2015 Trip spans 4 days
Delta
Delta
PBI
3:00a
MDW
10:12a
7h 12m
1 stop
MDW
3:15a
PBI
7:50a
4h 35m
1 stop
Depart: Sat May 9 2015 Return: Tue May 12 2015 Trip spans 4 days
Delta
Delta
BWI
9:45a
MDW
2:24p
4h 39m
1 stop
MDW
12:45p
BWI
4:09p
3h 24m
1 stop
Depart: Sun Apr 26 2015 Return: Wed Apr 29 2015 Trip spans 4 days
Delta
Delta
RDU
3:15a
MDW
8:49a
5h 34m
1 stop
MDW
3:00a
RDU
6:48a
3h 48m
1 stop
Depart: Mon Jun 1 2015 Return: Fri Jun 5 2015 Trip spans 5 days
Delta
Delta
CLT
2:15p
MDW
6:27p
4h 12m
1 stop
MDW
3:00a
CLT
7:09a
4h 09m
1 stop
Depart: Sun May 31 2015 Return: Fri Jun 19 2015 Trip spans 20 days
Delta
Delta
PHL
5:00a
MDW
10:12a
5h 12m
1 stop
MDW
3:15a
PHL
8:10a
4h 55m
1 stop
Depart: Sun Apr 5 2015 Return: Tue Apr 7 2015 Trip spans 3 days
Delta
Delta
BDL
3:05a
MDW
9:45a
6h 40m
1 stop
MDW
12:45p
BDL
6:21p
5h 36m
1 stop
Depart: Sun Mar 22 2015 Return: Thu Mar 26 2015 Trip spans 5 days
Delta
Delta
HOU
2:30a
MDW
7:51a
5h 21m
1 stop
MDW
2:45a
HOU
8:11a
5h 26m
1 stop
Change your search
Airports
Origin

Detroit
$201
Charlotte
$283
Raleigh
$268
Miami
$184
Omaha
$225
West Palm Beach
$246
San Francisco
$246
Baltimore
$262
Minneapolis
$97
Atlanta
$225
Columbus
$182
Trenton
$105
Hartford
$344
Newark
$232
Denver
$205
Dallas
only $222
only $222
Philadelphia
$316
Houston
$391
Boston
$184
Destination

Chicago
$97