Find Deals on Flights to Chicago Midway

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights to Chicago Midway

(Round-trip)
Depart: Wed Sep 9 2015 Return: Thu Sep 17 2015 Trip spans 9 days
Sun Country Air
Sun Country Air
MSP
MDW
1h 25m
nonstop
MDW
MSP
1h 25m
nonstop
Depart: Tue Oct 20 2015 Return: Wed Oct 21 2015 Trip spans 2 days
Southwest
Southwest
LGA
MDW
2h 20m
nonstop
MDW
LGA
2h 10m
nonstop
Depart: Wed Sep 23 2015 Return: Sat Sep 26 2015 Trip spans 4 days
Delta
Delta
ATL
MDW
1h 55m
nonstop
MDW
ATL
1h 47m
nonstop
Depart: Fri Oct 23 2015 Return: Mon Oct 26 2015 Trip spans 4 days
Delta
Delta
CMH
MDW
5h 13m
1 stop
MDW
CMH
4h 45m
1 stop
Depart: Wed Oct 21 2015 Return: Sat Oct 24 2015 Trip spans 4 days
Delta
Delta
OMA
MDW
3h 31m
1 stop
MDW
OMA
4h 42m
1 stop
Depart: Sun Sep 20 2015 Return: Tue Sep 22 2015 Trip spans 3 days
Delta
Delta
PHL
MDW
8h 05m
1 stop
MDW
PHL
4h 26m
1 stop
Depart: Fri Sep 25 2015 Return: Mon Sep 28 2015 Trip spans 4 days
Delta
Delta
PIT
MDW
5h 04m
1 stop
MDW
PIT
5h 17m
1 stop
Depart: Sat Oct 24 2015 Return: Tue Oct 27 2015 Trip spans 4 days
Delta
Delta
ABE
MDW
6h 01m
1 stop
MDW
ABE
3h 41m
1 stop
Depart: Fri Oct 2 2015 Return: Sun Oct 4 2015 Trip spans 3 days
Delta
Delta
CLT
MDW
4h 16m
1 stop
MDW
CLT
5h 40m
1 stop
Depart: Tue Nov 24 2015 Return: Tue Dec 1 2015 Trip spans 8 days
Delta
Delta
DCA
MDW
3h 34m
1 stop
MDW
DCA
3h 28m
1 stop
Depart: Wed Oct 7 2015 Return: Sat Oct 10 2015 Trip spans 4 days
Southwest
Southwest
BOS
MDW
3h 00m
nonstop
MDW
BOS
2h 15m
nonstop
Depart: Sat Sep 26 2015 Return: Tue Sep 29 2015 Trip spans 4 days
Delta
Delta
IAH
MDW
4h 44m
1 stop
MDW
IAH
4h 58m
1 stop
Depart: Wed Oct 14 2015 Return: Wed Oct 21 2015 Trip spans 8 days
Delta
Delta
RDU
MDW
4h 23m
1 stop
MDW
RDU
3h 59m
1 stop
Depart: Fri Oct 30 2015 Return: Sun Nov 1 2015 Trip spans 3 days
Delta
Delta
FLL
MDW
6h 15m
1 stop
MDW
FLL
4h 50m
1 stop
Depart: Mon Nov 2 2015 Return: Wed Nov 4 2015 Trip spans 3 days
Delta
Delta
JFK
MDW
5h 39m
1 stop
MDW
JFK
5h 48m
1 stop
Depart: Thu Nov 5 2015 Return: Tue Nov 10 2015 Trip spans 6 days
Delta
Delta
BWI
MDW
3h 44m
1 stop
MDW
BWI
3h 44m
1 stop
Depart: Thu Nov 19 2015 Return: Mon Nov 23 2015 Trip spans 5 days
Delta
Delta
MIA
MDW
6h 53m
1 stop
MDW
MIA
7h 42m
1 stop
Depart: Sun Dec 6 2015 Return: Sat Dec 12 2015 Trip spans 7 days
Delta
Delta
RIC
MDW
4h 10m
1 stop
MDW
RIC
5h 14m
1 stop
Depart: Wed Jan 20 2016 Return: Wed Jan 27 2016 Trip spans 8 days
Delta
Delta
PBI
MDW
4h 42m
1 stop
MDW
PBI
4h 45m
1 stop
Depart: Mon Sep 21 2015 Return: Sat Sep 26 2015 Trip spans 6 days
Delta
Delta
DFW
MDW
7h 38m
1 stop
MDW
DFW
5h 35m
1 stop
Airports
Origin

New York
only $184
only $92
Allentown
$164
Charlotte
$172
Raleigh
$184
Fort Lauderdale
$184
Washington
$174
Miami
$184
Omaha
$159
West Palm Beach
$184
Baltimore
$184
Minneapolis
$81
Atlanta
$127
Columbus
$144
Dallas
$188
Philadelphia
$164
Houston
$184
Richmond
$184
Boston
$175
Pittsburgh
$164
Destination

Chicago
$81