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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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: Wed Aug 26 2015 Return: Wed Sep 2 2015 Trip spans 8 days
Delta
Delta
ATL
MDW
2h 02m
nonstop
MDW
ATL
1h 59m
nonstop
Depart: Wed Nov 11 2015 Return: Sat Nov 14 2015 Trip spans 4 days
Delta
Delta
PHL
MDW
5h 27m
1 stop
MDW
PHL
3h 45m
1 stop
Depart: Fri Jan 1 2016 Return: Mon Jan 4 2016 Trip spans 4 days
Southwest
Southwest
BWI
MDW
2h 05m
nonstop
MDW
BWI
1h 45m
nonstop
Depart: Tue Aug 25 2015 Return: Sat Aug 29 2015 Trip spans 5 days
Delta
Delta
SLC
MDW
3h 03m
nonstop
MDW
SLC
3h 29m
nonstop
Depart: Thu Oct 1 2015 Return: Sat Oct 3 2015 Trip spans 3 days
Delta
Delta
HPN
MDW
4h 52m
1 stop
MDW
HPN
7h 30m
1 stop
Depart: Sat Aug 15 2015 Return: Tue Aug 18 2015 Trip spans 4 days
Delta
Delta
IAH
MDW
7h 52m
1 stop
MDW
IAH
7h 55m
1 stop
Depart: Sat Aug 29 2015 Return: Mon Aug 31 2015 Trip spans 3 days
Delta
Delta
BDL
MDW
5h 55m
1 stop
MDW
BDL
3h 59m
1 stop
Depart: Mon Aug 31 2015 Return: Wed Sep 2 2015 Trip spans 3 days
Delta
Delta
AUS
MDW
5h 05m
1 stop
MDW
AUS
5h 27m
1 stop
Depart: Fri Sep 11 2015 Return: Wed Sep 16 2015 Trip spans 6 days
Delta
Delta
EWR
MDW
3h 42m
1 stop
MDW
EWR
4h 13m
1 stop
Depart: Sat Sep 19 2015 Return: Mon Sep 28 2015 Trip spans 10 days
Delta
Delta
TPA
MDW
4h 37m
1 stop
MDW
TPA
4h 21m
1 stop
Depart: Tue Sep 22 2015 Return: Tue Sep 29 2015 Trip spans 8 days
Delta
Delta
MIA
MDW
5h 14m
1 stop
MDW
MIA
4h 52m
1 stop
Depart: Wed Sep 23 2015 Return: Sat Sep 26 2015 Trip spans 4 days
Delta
Delta
BOS
MDW
6h 00m
1 stop
MDW
BOS
5h 26m
1 stop
Depart: Fri Sep 25 2015 Return: Tue Sep 29 2015 Trip spans 5 days
Delta
Delta
MSY
MDW
5h 01m
1 stop
MDW
MSY
4h 35m
1 stop
Depart: Sat Sep 26 2015 Return: Mon Sep 28 2015 Trip spans 3 days
Delta
Delta
HOU
MDW
8h 12m
1 stop
MDW
HOU
7h 22m
1 stop
Depart: Wed Oct 7 2015 Return: Wed Oct 21 2015 Trip spans 15 days
Delta
Delta
DFW
MDW
4h 43m
1 stop
MDW
DFW
4h 58m
1 stop
Depart: Fri Oct 23 2015 Return: Mon Oct 26 2015 Trip spans 4 days
Delta
Delta
RDU
MDW
3h 38m
1 stop
MDW
RDU
4h 09m
1 stop
Depart: Mon Nov 2 2015 Return: Mon Nov 9 2015 Trip spans 8 days
Delta
Delta
JFK
MDW
4h 27m
1 stop
MDW
JFK
3h 42m
1 stop
Depart: Tue Nov 3 2015 Return: Sat Nov 7 2015 Trip spans 5 days
Delta
Delta
DAL
MDW
4h 37m
1 stop
MDW
DAL
6h 10m
1 stop
Depart: Wed Aug 12 2015 Return: Tue Aug 18 2015 Trip spans 7 days
Delta
Delta
MCO
MDW
4h 48m
1 stop
MDW
MCO
4h 41m
1 stop
Airports
Origin

New York
$184
Raleigh
$184
White Plains
$179
Austin
$184
Miami
$184
Baltimore
$176
Minneapolis
$81
Atlanta
$137
Orlando
$186
New Orleans
$184
Salt Lake City
$177
Hartford
$184
Newark
$184
Dallas
only $184
only $184
Tampa
$184
Philadelphia
$164
Houston
only $184
only $184
Boston
$184
Destination

Chicago
$81