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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: 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: Wed Dec 24 2014 Return: Thu Dec 25 2014 Trip spans 2 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: Tue Feb 3 2015 Return: Wed Feb 4 2015 Trip spans 2 days
Delta
Delta
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Tue Feb 24 2015 Return: Tue Mar 3 2015 Trip spans 8 days
Delta
Delta
MIA
4:00a
MDW
10:42a
6h 42m
1 stop
MDW
7:30a
MIA
12:04p
4h 34m
1 stop
Depart: Tue Dec 30 2014 Return: Tue Jan 6 2015 Trip spans 8 days
Delta
Delta
DTW
2:50p
MDW
4:14p
1h 24m
nonstop
MDW
1:35p
DTW
2:44p
1h 09m
nonstop
Depart: Sat Apr 11 2015 Return: Wed Apr 15 2015 Trip spans 5 days
Delta
Delta
DFW
6:45a
MDW
1:14p
6h 29m
1 stop
MDW
2:45a
DFW
7:34a
4h 49m
1 stop
Depart: Wed May 6 2015 Return: Sat May 16 2015 Trip spans 11 days
Delta
Delta
DAL
6:05a
MDW
10:42a
4h 37m
1 stop
MDW
3:15a
DAL
8:10a
4h 55m
1 stop
Depart: Wed Apr 8 2015 Return: Thu Apr 9 2015 Trip spans 2 days
Delta
Delta
ATL
2:55p
MDW
4:54p
1h 59m
nonstop
MDW
8:30a
ATL
10:20a
1h 50m
nonstop
Depart: Wed May 27 2015 Return: Wed Jun 3 2015 Trip spans 8 days
Delta
Delta
OMA
11:30a
MDW
4:53p
5h 23m
1 stop
MDW
5:05a
OMA
10:25a
5h 20m
1 stop
Depart: Sat Apr 18 2015 Return: Tue Apr 21 2015 Trip spans 4 days
Delta
Delta
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
MDW
11:10a
SJC
5:46p
6h 36m
1 stop
Depart: Wed Apr 22 2015 Return: Sat Apr 25 2015 Trip spans 4 days
Delta
Delta
SFO
8:35p
MDW
2:33a
5h 58m
1 stop
MDW
8:10a
SFO
2:28p
6h 18m
1 stop
Depart: Sat Dec 20 2014 Return: Sun Jan 4 2015 Trip spans 16 days
Delta
Delta
PBI
12:50p
MDW
6:16p
5h 26m
1 stop
MDW
1:00a
PBI
5:45a
4h 45m
1 stop
Depart: Sun Apr 26 2015 Return: Thu Apr 30 2015 Trip spans 5 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 Apr 27 2015 Return: Sat May 2 2015 Trip spans 6 days
Delta
Delta
SLC
8:55p
MDW
4:04a
7h 09m
1 stop
MDW
1:10p
SLC
6:02p
4h 52m
1 stop
Depart: Tue May 26 2015 Return: Wed May 27 2015 Trip spans 2 days
Delta
Delta
MSY
5:15a
MDW
9:12a
3h 57m
1 stop
MDW
3:15a
MSY
7:24a
4h 09m
1 stop
Depart: Sun May 17 2015 Return: Mon May 18 2015 Trip spans 2 days
Delta
Delta
SEA
5:00a
MDW
10:51a
5h 51m
1 stop
MDW
8:40a
SEA
5:20p
8h 40m
1 stop
Change your search
Airports
Origin

Detroit
$196
Seattle
$392
Raleigh
$268
San Jose
$246
Miami
$184
Omaha
$225
West Palm Beach
$265
San Francisco
$246
Minneapolis
$107
Atlanta
$225
New Orleans
$292
Salt Lake City
$282
Trenton
$105
Dallas
only $222
only $222
Boston
$184
Destination

Chicago
$105