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Find Deals on Flights 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: Sat Jul 25 2015 Return: Tue Jul 28 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MSP
MDW
1h 25m
nonstop
MDW
MSP
1h 25m
nonstop
Depart: Sat Aug 22 2015 Return: Tue Aug 25 2015 Trip spans 4 days
Delta
Delta
ATL
MDW
2h 01m
nonstop
MDW
ATL
1h 59m
nonstop
Depart: Tue Jul 14 2015 Return: Wed Jul 15 2015 Trip spans 2 days
Delta
Delta
PHL
MDW
7h 20m
1 stop
MDW
PHL
3h 52m
1 stop
Depart: Wed Aug 26 2015 Return: Mon Aug 31 2015 Trip spans 6 days
Delta
Delta
RDU
MDW
4h 12m
1 stop
MDW
RDU
3h 57m
1 stop
Depart: Tue Aug 25 2015 Return: Wed Aug 26 2015 Trip spans 2 days
Delta
Delta
DCA
MDW
4h 44m
1 stop
MDW
DCA
3h 53m
1 stop
Depart: Tue Sep 8 2015 Return: Tue Sep 15 2015 Trip spans 8 days
Delta
Delta
IAD
MDW
3h 53m
1 stop
MDW
IAD
4h 52m
1 stop
Depart: Tue Jul 28 2015 Return: Thu Aug 13 2015 Trip spans 17 days
Delta
Delta
HOU
MDW
5h 03m
1 stop
MDW
HOU
5h 18m
1 stop
Depart: Wed Aug 5 2015 Return: Fri Aug 21 2015 Trip spans 17 days
Delta
Delta
IAH
MDW
5h 03m
1 stop
MDW
IAH
5h 19m
1 stop
Depart: Sat Oct 24 2015 Return: Mon Oct 26 2015 Trip spans 3 days
Delta
Delta
TPA
MDW
4h 59m
1 stop
MDW
TPA
4h 37m
1 stop
Depart: Thu Nov 19 2015 Return: Mon Nov 23 2015 Trip spans 5 days
Delta
Delta
DEN
MDW
7h 15m
1 stop
MDW
DEN
6h 16m
1 stop
Depart: Wed Sep 30 2015 Return: Mon Oct 5 2015 Trip spans 6 days
Delta
Delta
SLC
MDW
3h 06m
nonstop
MDW
SLC
3h 31m
nonstop
Depart: Wed Aug 12 2015 Return: Wed Aug 19 2015 Trip spans 8 days
Delta
Delta
MCO
MDW
6h 51m
1 stop
MDW
MCO
6h 20m
1 stop
Depart: Wed Sep 2 2015 Return: Sat Sep 5 2015 Trip spans 4 days
Delta
Delta
CMH
MDW
4h 40m
1 stop
MDW
CMH
4h 43m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
Delta
Delta
BWI
MDW
3h 59m
1 stop
MDW
BWI
4h 40m
1 stop
Depart: Sat Sep 12 2015 Return: Mon Sep 14 2015 Trip spans 3 days
Delta
Delta
BOS
MDW
6h 07m
1 stop
MDW
BOS
5h 32m
1 stop
Depart: Fri Nov 20 2015 Return: Mon Nov 23 2015 Trip spans 4 days
Delta
Delta
DTW
MDW
1h 15m
nonstop
MDW
DTW
1h 10m
nonstop
Depart: Tue Oct 27 2015 Return: Tue Nov 3 2015 Trip spans 8 days
Delta
Delta
PHX
MDW
7h 46m
1 stop
MDW
PHX
7h 08m
1 stop
Depart: Sat Sep 26 2015 Return: Tue Sep 29 2015 Trip spans 4 days
Delta
Delta
MEM
MDW
4h 22m
1 stop
MDW
MEM
5h 35m
1 stop
Depart: Sat Oct 10 2015 Return: Wed Oct 14 2015 Trip spans 5 days
Delta
Delta
OMA
MDW
3h 45m
1 stop
MDW
OMA
3h 59m
1 stop
Depart: Thu Oct 15 2015 Return: Mon Oct 19 2015 Trip spans 5 days
Delta
Delta
PIT
MDW
6h 37m
1 stop
MDW
PIT
3h 24m
1 stop
Airports
Origin

Detroit
$209
Raleigh
$164
Washington
only $174
only $174
Omaha
$223
Baltimore
$196
Minneapolis
$107
Atlanta
$157
Orlando
$186
Columbus
$192
Phoenix
$216
Memphis
$223
Salt Lake City
$185
Denver
$184
Tampa
$184
Philadelphia
$164
Houston
only $184
only $184
Boston
$200
Pittsburgh
$228
Destination

Chicago
$107