Browse Origins:
Browse Destinations:

Find Flight Deals from United States 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: Mon May 18 2015 Return: Thu May 21 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MSP
MDW
1h 25m
nonstop
MDW
MSP
1h 25m
nonstop
Depart: Thu May 28 2015 Return: Tue Jun 9 2015 Trip spans 13 days
Delta
Delta
MCI
MDW
5h 35m
1 stop
MDW
MCI
5h 16m
1 stop
Depart: Sat May 2 2015 Return: Tue May 5 2015 Trip spans 4 days
Delta
Delta
OMA
MDW
4h 28m
1 stop
MDW
OMA
4h 21m
1 stop
Depart: Tue May 12 2015 Return: Tue May 19 2015 Trip spans 8 days
Delta
Delta
DAL
MDW
4h 47m
1 stop
MDW
DAL
5h 06m
1 stop
Depart: Sat May 16 2015 Return: Wed May 20 2015 Trip spans 5 days
Delta
Delta
MSY
MDW
4h 53m
1 stop
MDW
MSY
6h 27m
1 stop
Depart: Wed May 20 2015 Return: Wed Jun 3 2015 Trip spans 15 days
Delta
Delta
MIA
MDW
7h 03m
1 stop
MDW
MIA
4h 57m
1 stop
Depart: Thu May 21 2015 Return: Wed May 27 2015 Trip spans 7 days
Delta
Delta
FLL
MDW
4h 44m
1 stop
MDW
FLL
4h 55m
1 stop
Depart: Tue May 26 2015 Return: Mon Jun 8 2015 Trip spans 14 days
Delta
Delta
PBI
MDW
5h 15m
1 stop
MDW
PBI
4h 52m
1 stop
Depart: Wed May 27 2015 Return: Fri May 29 2015 Trip spans 3 days
Delta
Delta
BOS
MDW
6h 06m
1 stop
MDW
BOS
5h 18m
1 stop
Depart: Sat May 30 2015 Return: Tue Jun 2 2015 Trip spans 4 days
Delta
Delta
DFW
MDW
5h 20m
1 stop
MDW
DFW
5h 16m
1 stop
Depart: Wed Jun 3 2015 Return: Fri Jun 5 2015 Trip spans 3 days
Delta
Delta
HOU
MDW
4h 45m
1 stop
MDW
HOU
5h 15m
1 stop
Depart: Sat Jul 18 2015 Return: Wed Jul 22 2015 Trip spans 5 days
Delta
Delta
IAH
MDW
5h 03m
1 stop
MDW
IAH
5h 16m
1 stop
Depart: Wed May 6 2015 Return: Fri May 15 2015 Trip spans 10 days
Delta
Delta
TPA
MDW
5h 17m
1 stop
MDW
TPA
6h 58m
1 stop
Depart: Tue Aug 11 2015 Return: Wed Aug 19 2015 Trip spans 9 days
Delta
Delta
PHX
MDW
8h 10m
1 stop
MDW
PHX
5h 31m
1 stop
Depart: Sun May 17 2015 Return: Mon May 18 2015 Trip spans 2 days
Delta
Delta
DTW
MDW
1h 13m
nonstop
MDW
DTW
1h 10m
nonstop
Depart: Sun Jun 14 2015 Return: Mon Jun 15 2015 Trip spans 2 days
Delta
Delta
EWR
MDW
5h 16m
1 stop
MDW
EWR
5h 13m
1 stop
Depart: Sat May 9 2015 Return: Sat May 16 2015 Trip spans 8 days
Delta
Delta
JFK
MDW
4h 39m
1 stop
MDW
JFK
4h 30m
1 stop
Depart: Fri Aug 7 2015 Return: Mon Aug 10 2015 Trip spans 4 days
Delta
Delta
PIT
MDW
5h 19m
1 stop
MDW
PIT
5h 24m
1 stop
Depart: Sat Sep 12 2015 Return: Sat Sep 19 2015 Trip spans 8 days
Delta
Delta
IAD
MDW
7h 24m
1 stop
MDW
IAD
4h 44m
1 stop
Depart: Tue Sep 15 2015 Return: Mon Sep 21 2015 Trip spans 7 days
Delta
Delta
BWI
MDW
3h 25m
1 stop
MDW
BWI
4h 41m
1 stop
Airports
Origin

New York
$244
Kansas City
$164
Detroit
$219
Fort Lauderdale
$184
Washington
$244
Miami
$184
Omaha
$179
West Palm Beach
$184
Baltimore
$244
Minneapolis
$99
New Orleans
$184
Phoenix
$204
Newark
$232
Dallas
only $184
only $184
Tampa
$194
Houston
only $184
only $184
Boston
$184
Pittsburgh
$244
Destination

Chicago
$99