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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 Feb 9 2015 Return: Thu Feb 12 2015 Trip spans 4 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: Mon Feb 2 2015 Return: Wed Feb 11 2015 Trip spans 10 days
Frontier
Frontier
TTN
1:25a
MDW
3:45a
2h 20m
nonstop
MDW
12:35p
TTN
2:20p
1h 45m
nonstop
Depart: Sat May 2 2015 Return: Wed May 6 2015 Trip spans 5 days
Delta
Delta
DTW
4:20a
MDW
5:45a
1h 25m
nonstop
MDW
5:15a
DTW
6:30a
1h 15m
nonstop
Depart: Sat Feb 7 2015 Return: Mon Feb 9 2015 Trip spans 3 days
Delta
Delta
OMA
1:45a
MDW
6:06a
4h 21m
1 stop
MDW
11:31a
OMA
4:07p
4h 36m
1 stop
Depart: Wed May 6 2015 Return: Sat May 9 2015 Trip spans 4 days
Delta
Delta
MEM
6:43a
MDW
10:42a
3h 59m
1 stop
MDW
2:45a
MEM
7:15a
4h 30m
1 stop
Depart: Tue Feb 10 2015 Return: Wed Feb 11 2015 Trip spans 2 days
Delta
Delta
HOU
8:57a
MDW
1:50p
4h 53m
1 stop
MDW
7:05a
HOU
12:19p
5h 14m
1 stop
Depart: Tue May 19 2015 Return: Wed May 27 2015 Trip spans 9 days
Delta
Delta
CMH
4:30a
MDW
8:49a
4h 19m
1 stop
MDW
3:00a
CMH
5:59a
2h 59m
1 stop
Depart: Wed Jun 3 2015 Return: Tue Jun 9 2015 Trip spans 7 days
Delta
Delta
TPA
6:45a
MDW
11:42a
4h 57m
1 stop
MDW
9:50a
TPA
2:00p
4h 10m
1 stop
Depart: Sat Jun 6 2015 Return: Tue Jun 9 2015 Trip spans 4 days
Delta
Delta
BOS
12:00p
MDW
6:27p
6h 27m
1 stop
MDW
8:30a
BOS
2:10p
5h 40m
1 stop
Depart: Wed Jun 17 2015 Return: Sun Jun 21 2015 Trip spans 5 days
Delta
Delta
MSY
5:15a
MDW
9:12a
3h 57m
1 stop
MDW
3:15a
MSY
8:24a
5h 09m
1 stop
Depart: Sat Jun 13 2015 Return: Tue Jun 16 2015 Trip spans 4 days
Delta
Delta
CLE
12:29p
MDW
4:54p
4h 25m
1 stop
MDW
3:15a
CLE
8:52a
5h 37m
1 stop
Depart: Mon Jul 13 2015 Return: Tue Jul 28 2015 Trip spans 16 days
Delta
Delta
PHX
5:10a
MDW
10:51a
5h 41m
1 stop
MDW
7:05a
PHX
12:40p
5h 35m
1 stop
Depart: Mon Jul 6 2015 Return: Fri Jul 17 2015 Trip spans 12 days
Delta
Delta
MIA
11:30a
MDW
5:53p
6h 23m
1 stop
MDW
2:45a
MIA
8:32a
5h 47m
1 stop
Depart: Tue Feb 3 2015 Return: Wed Mar 4 2015 Trip spans 30 days
Delta
Delta
FLL
7:45a
MDW
1:18p
5h 33m
1 stop
MDW
10:37a
FLL
3:02p
4h 25m
1 stop
Depart: Sun Jun 21 2015 Return: Tue Jun 23 2015 Trip spans 3 days
Delta
Delta
DFW
10:15a
MDW
2:47p
4h 32m
1 stop
MDW
5:05a
DFW
9:45a
4h 40m
1 stop
Change your search
Airports
Origin

Detroit
$167
Fort Lauderdale
$234
Cleveland
$204
Miami
$224
Omaha
$179
Minneapolis
$81
New Orleans
$184
Columbus
$182
Phoenix
$204
Memphis
$179
Trenton
$82
Dallas
$252
Tampa
$184
Houston
$182
Boston
$184
Destination

Chicago
$81