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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 Jan 20 2015 Return: Wed Jan 28 2015 Trip spans 9 days
Delta
Delta
BOS
1:00a
MDW
7:53a
6h 53m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Tue Jun 9 2015 Return: Tue Jun 23 2015 Trip spans 15 days
Delta
Delta
MIA
6:15a
MDW
11:42a
5h 27m
1 stop
MDW
3:15a
MIA
7:54a
4h 39m
1 stop
Depart: Sun Mar 1 2015 Return: Wed Mar 4 2015 Trip spans 4 days
Delta
Delta
CLE
4:55a
MDW
10:39a
5h 44m
1 stop
MDW
5:10a
CLE
9:49a
4h 39m
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: Mon Apr 6 2015 Return: Thu Apr 9 2015 Trip spans 4 days
Delta
Delta
CMH
3:30p
MDW
7:02p
3h 32m
1 stop
MDW
2:00a
CMH
6:35a
4h 35m
1 stop
Depart: Sat Apr 18 2015 Return: Sun Apr 19 2015 Trip spans 2 days
Delta
Delta
DFW
8:00a
MDW
3:54p
7h 54m
1 stop
MDW
7:05a
DFW
11:46a
4h 41m
1 stop
Depart: Tue Mar 10 2015 Return: Wed Mar 18 2015 Trip spans 9 days
Delta
Delta
ATL
12:15p
MDW
2:14p
1h 59m
nonstop
MDW
9:50a
ATL
11:40a
1h 50m
nonstop
Depart: Tue May 5 2015 Return: Sat May 9 2015 Trip spans 5 days
Delta
Delta
OMA
11:30a
MDW
2:47p
3h 17m
1 stop
MDW
2:45a
OMA
6:23a
3h 38m
1 stop
Depart: Tue Feb 24 2015 Return: Thu Feb 26 2015 Trip spans 3 days
Delta
Delta
EWR
1:30a
MDW
7:50a
6h 20m
1 stop
MDW
7:28a
EWR
12:49p
5h 21m
1 stop
Depart: Tue Jan 6 2015 Return: Thu Jan 8 2015 Trip spans 3 days
Delta
Delta
DAL
5:10a
MDW
9:40a
4h 30m
1 stop
MDW
2:10a
DAL
7:16a
5h 06m
1 stop
Depart: Mon Apr 13 2015 Return: Wed Apr 15 2015 Trip spans 3 days
Delta
Delta
SFO
8:35p
MDW
2:33a
5h 58m
1 stop
MDW
8:10a
SFO
2:28p
6h 18m
1 stop
Depart: Mon Apr 27 2015 Return: Tue May 5 2015 Trip spans 9 days
Delta
Delta
FLL
11:45a
MDW
4:54p
5h 09m
1 stop
MDW
3:15a
FLL
7:55a
4h 40m
1 stop
Depart: Sun Dec 28 2014 Return: Tue Jan 13 2015 Trip spans 17 days
Delta
Delta
MEM
1:00a
MDW
5:40a
4h 40m
1 stop
MDW
11:31a
MEM
3:48p
4h 17m
1 stop
Depart: Wed May 20 2015 Return: Sat May 23 2015 Trip spans 4 days
Delta
Delta
SJC
2:10a
MDW
11:50a
9h 40m
2 stops
MDW
8:10a
SJC
5:46p
9h 36m
1 stop
Depart: Mon Jun 22 2015 Return: Sat Jun 27 2015 Trip spans 6 days
Delta
Delta
RDU
12:40p
MDW
5:15p
4h 35m
1 stop
MDW
8:10a
RDU
1:30p
5h 20m
1 stop
Depart: Sat Jun 13 2015 Return: Wed Jun 17 2015 Trip spans 5 days
Delta
Delta
HOU
5:40a
MDW
10:30a
4h 50m
1 stop
MDW
9:50a
HOU
2:33p
4h 43m
1 stop
Depart: Sat Jun 6 2015 Return: Wed Jun 10 2015 Trip spans 5 days
Delta
Delta
PHL
11:15a
MDW
4:54p
5h 39m
1 stop
MDW
9:50a
PHL
2:55p
5h 05m
1 stop
Depart: Sun Apr 19 2015 Return: Thu Apr 23 2015 Trip spans 5 days
Delta
Delta
PBI
9:55a
MDW
2:50p
4h 55m
1 stop
MDW
9:50a
PBI
4:15p
6h 25m
1 stop
Change your search
Airports
Origin

Detroit
$201
Raleigh
$280
Fort Lauderdale
$249
Cleveland
$196
San Jose
$270
Miami
$184
Omaha
$225
West Palm Beach
$340
San Francisco
$246
Minneapolis
$97
Atlanta
$225
Columbus
$210
Memphis
$268
Trenton
$105
Newark
$232
Dallas
only $222
only $234
Philadelphia
$316
Houston
$282
Boston
$184
Destination

Chicago
$97