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: Mon Aug 24 2015 Return: Fri Aug 28 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MSP
MDW
1h 25m
nonstop
MDW
MSP
1h 25m
nonstop
Depart: Thu Aug 27 2015 Return: Fri Aug 28 2015 Trip spans 2 days
Delta
Delta
ATL
MDW
2h 04m
nonstop
MDW
ATL
1h 57m
nonstop
Depart: Thu Oct 29 2015 Return: Mon Nov 2 2015 Trip spans 5 days
Delta
Delta
JFK
MDW
4h 12m
1 stop
MDW
JFK
3h 42m
1 stop
Depart: Sat Aug 29 2015 Return: Tue Sep 1 2015 Trip spans 4 days
Delta
Delta
HPN
MDW
7h 50m
1 stop
MDW
HPN
4h 12m
1 stop
Depart: Tue Aug 11 2015 Return: Sat Aug 22 2015 Trip spans 12 days
Delta
Delta
MSY
MDW
4h 29m
1 stop
MDW
MSY
6h 11m
1 stop
Depart: Tue Aug 25 2015 Return: Tue Sep 1 2015 Trip spans 8 days
Delta
Delta
EWR
MDW
3h 58m
1 stop
MDW
EWR
3h 54m
1 stop
Depart: Sat Sep 19 2015 Return: Wed Sep 23 2015 Trip spans 5 days
Delta
Delta
BOS
MDW
4h 25m
1 stop
MDW
BOS
3h 54m
1 stop
Depart: Fri Sep 25 2015 Return: Mon Sep 28 2015 Trip spans 4 days
Delta
Delta
BDL
MDW
5h 49m
1 stop
MDW
BDL
5h 26m
1 stop
Depart: Sun Oct 4 2015 Return: Tue Oct 6 2015 Trip spans 3 days
Delta
Delta
DAL
MDW
6h 15m
1 stop
MDW
DAL
7h 52m
1 stop
Depart: Wed Oct 21 2015 Return: Tue Oct 27 2015 Trip spans 7 days
Delta
Delta
AUS
MDW
6h 26m
1 stop
MDW
AUS
5h 14m
1 stop
Depart: Fri Oct 23 2015 Return: Mon Oct 26 2015 Trip spans 4 days
Delta
Delta
IAH
MDW
5h 54m
1 stop
MDW
IAH
4h 57m
1 stop
Depart: Mon Nov 23 2015 Return: Tue Dec 1 2015 Trip spans 9 days
Delta
Delta
RDU
MDW
6h 19m
1 stop
MDW
RDU
4h 07m
1 stop
Depart: Tue Jan 12 2016 Return: Sun Jan 17 2016 Trip spans 6 days
Delta
Delta
HOU
MDW
4h 42m
1 stop
MDW
HOU
4h 43m
1 stop
Depart: Fri Jan 29 2016 Return: Tue Feb 2 2016 Trip spans 5 days
Delta
Delta
DFW
MDW
4h 42m
1 stop
MDW
DFW
4h 40m
1 stop
Depart: Tue Sep 22 2015 Return: Mon Sep 28 2015 Trip spans 7 days
Delta
Delta
DEN
MDW
4h 24m
1 stop
MDW
DEN
7h 23m
1 stop
Depart: Sat Aug 22 2015 Return: Tue Aug 25 2015 Trip spans 4 days
Delta
Delta
PHL
MDW
4h 07m
1 stop
MDW
PHL
4h 05m
1 stop
Depart: Tue Sep 1 2015 Return: Sat Sep 5 2015 Trip spans 5 days
Delta
Delta
DCA
MDW
4h 40m
1 stop
MDW
DCA
4h 50m
1 stop
Depart: Sat Sep 5 2015 Return: Thu Sep 10 2015 Trip spans 6 days
Delta
Delta
TPA
MDW
4h 20m
1 stop
MDW
TPA
4h 49m
1 stop
Depart: Tue Jan 5 2016 Return: Thu Jan 7 2016 Trip spans 3 days
Delta
Delta
IAD
MDW
4h 52m
1 stop
MDW
IAD
3h 30m
1 stop
Depart: Mon Oct 5 2015 Return: Mon Oct 12 2015 Trip spans 8 days
Delta
Delta
DTW
MDW
1h 14m
nonstop
MDW
DTW
1h 14m
nonstop
Airports
Origin

New York
$164
Detroit
$199
Raleigh
$184
White Plains
$179
Austin
$184
Washington
only $194
only $194
Minneapolis
$81
Atlanta
$137
New Orleans
$184
Hartford
$184
Newark
$184
Denver
$188
Dallas
only $184
only $184
Tampa
$194
Philadelphia
$190
Houston
only $184
only $184
Boston
$184
Destination

Chicago
$81