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: Fri Sep 11 2015 Trip spans 3 days
Sun Country Air
Sun Country Air
MSP
MDW
1h 25m
nonstop
MDW
MSP
1h 25m
nonstop
Depart: Tue Sep 29 2015 Return: Sun Oct 4 2015 Trip spans 6 days
Delta
Delta
ATL
MDW
1h 55m
nonstop
MDW
ATL
1h 51m
nonstop
Depart: Fri Oct 16 2015 Return: Wed Oct 21 2015 Trip spans 6 days
Southwest
Southwest
BWI
MDW
2h 05m
nonstop
MDW
BWI
1h 45m
nonstop
Depart: Sat Sep 19 2015 Return: Wed Sep 23 2015 Trip spans 5 days
Southwest
Southwest
LGA
MDW
2h 30m
nonstop
MDW
LGA
2h 00m
nonstop
Depart: Tue Sep 22 2015 Return: Fri Sep 25 2015 Trip spans 4 days
Delta
Delta
PHL
MDW
4h 57m
1 stop
MDW
PHL
4h 03m
1 stop
Depart: Wed Sep 30 2015 Return: Sat Oct 3 2015 Trip spans 4 days
Delta
Delta
ABE
MDW
6h 50m
1 stop
MDW
ABE
6h 49m
1 stop
Depart: Wed Sep 16 2015 Return: Sat Sep 19 2015 Trip spans 4 days
Southwest
Southwest
BOS
MDW
2h 50m
nonstop
MDW
BOS
2h 15m
nonstop
Depart: Mon Sep 21 2015 Return: Fri Sep 25 2015 Trip spans 5 days
Delta
Delta
RDU
MDW
4h 37m
1 stop
MDW
RDU
4h 00m
1 stop
Depart: Fri Sep 25 2015 Return: Mon Sep 28 2015 Trip spans 4 days
Delta
Delta
PBI
MDW
6h 37m
1 stop
MDW
PBI
5h 51m
1 stop
Depart: Sat Oct 17 2015 Return: Tue Oct 20 2015 Trip spans 4 days
Delta
Delta
IAH
MDW
7h 34m
1 stop
MDW
IAH
4h 57m
1 stop
Depart: Fri Oct 23 2015 Return: Mon Oct 26 2015 Trip spans 4 days
Delta
Delta
JFK
MDW
7h 25m
1 stop
MDW
JFK
7h 37m
1 stop
Depart: Tue Dec 8 2015 Return: Mon Dec 14 2015 Trip spans 7 days
Delta
Delta
MIA
MDW
4h 47m
1 stop
MDW
MIA
4h 34m
1 stop
Depart: Wed Dec 9 2015 Return: Wed Dec 16 2015 Trip spans 8 days
Delta
Delta
HOU
MDW
5h 56m
1 stop
MDW
HOU
5h 10m
1 stop
Depart: Wed Dec 23 2015 Return: Mon Jan 11 2016 Trip spans 20 days
Delta
Delta
FLL
MDW
5h 19m
1 stop
MDW
FLL
6h 13m
1 stop
Depart: Tue Nov 3 2015 Return: Thu Nov 19 2015 Trip spans 17 days
Delta
Delta
CMH
MDW
4h 14m
1 stop
MDW
CMH
4h 33m
1 stop
Depart: Wed Oct 7 2015 Return: Tue Oct 13 2015 Trip spans 7 days
Delta
Delta
EWR
MDW
3h 43m
1 stop
MDW
EWR
3h 51m
1 stop
Depart: Sun Nov 15 2015 Return: Fri Nov 20 2015 Trip spans 6 days
Delta
Delta
DFW
MDW
4h 39m
1 stop
MDW
DFW
4h 52m
1 stop
Depart: Wed Jan 13 2016 Return: Sun Jan 17 2016 Trip spans 5 days
Delta
Delta
DAL
MDW
4h 37m
1 stop
MDW
DAL
4h 55m
1 stop
Depart: Wed Oct 21 2015 Return: Sat Oct 24 2015 Trip spans 4 days
Delta
Delta
IAD
MDW
3h 28m
1 stop
MDW
IAD
3h 15m
1 stop
Depart: Tue Dec 1 2015 Return: Mon Dec 7 2015 Trip spans 7 days
Delta
Delta
DCA
MDW
3h 30m
1 stop
MDW
DCA
3h 16m
1 stop
Airports
Origin

New York
only $184
only $161
Allentown
$164
Raleigh
$184
Fort Lauderdale
$184
Washington
only $194
only $194
Miami
$184
West Palm Beach
$184
Baltimore
$160
Minneapolis
$81
Atlanta
$127
Columbus
$186
Newark
$188
Dallas
only $188
only $188
Philadelphia
$164
Houston
only $184
only $184
Boston
$170
Destination

Chicago
$81