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: Tue May 5 2015 Return: Fri May 8 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MSP
MDW
1h 25m
nonstop
MDW
MSP
1h 25m
nonstop
Depart: Wed May 6 2015 Return: Fri May 8 2015 Trip spans 3 days
Delta
Delta
DTW
MDW
1h 10m
nonstop
MDW
DTW
1h 10m
nonstop
Depart: Wed Apr 8 2015 Return: Sat Apr 11 2015 Trip spans 4 days
Delta
Delta
DAL
MDW
4h 41m
1 stop
MDW
DAL
6h 51m
1 stop
Depart: Wed Apr 15 2015 Return: Tue Apr 21 2015 Trip spans 7 days
Delta
Delta
DFW
MDW
5h 09m
1 stop
MDW
DFW
5h 27m
1 stop
Depart: Sat Apr 18 2015 Return: Tue Apr 21 2015 Trip spans 4 days
Delta
Delta
FLL
MDW
6h 06m
1 stop
MDW
FLL
4h 36m
1 stop
Depart: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
Delta
Delta
IAH
MDW
4h 31m
1 stop
MDW
IAH
5h 16m
1 stop
Depart: Sat May 2 2015 Return: Mon May 4 2015 Trip spans 3 days
Delta
Delta
BOS
MDW
6h 37m
1 stop
MDW
BOS
5h 19m
1 stop
Depart: Fri May 15 2015 Return: Sun May 17 2015 Trip spans 3 days
Delta
Delta
PBI
MDW
7h 28m
1 stop
MDW
PBI
4h 35m
1 stop
Depart: Thu May 28 2015 Return: Mon Jun 1 2015 Trip spans 5 days
Delta
Delta
MIA
MDW
5h 43m
1 stop
MDW
MIA
4h 57m
1 stop
Depart: Fri May 29 2015 Return: Mon Jun 1 2015 Trip spans 4 days
Delta
Delta
TPA
MDW
4h 39m
1 stop
MDW
TPA
5h 03m
1 stop
Depart: Sun May 31 2015 Return: Wed Jun 3 2015 Trip spans 4 days
Delta
Delta
HOU
MDW
5h 02m
1 stop
MDW
HOU
4h 47m
1 stop
Depart: Tue Jun 23 2015 Return: Thu Jun 25 2015 Trip spans 3 days
Delta
Delta
MSY
MDW
5h 28m
1 stop
MDW
MSY
7h 06m
1 stop
Depart: Sat May 9 2015 Return: Mon May 18 2015 Trip spans 10 days
Delta
Delta
PIT
MDW
4h 41m
1 stop
MDW
PIT
3h 22m
1 stop
Depart: Tue Apr 28 2015 Return: Sat May 2 2015 Trip spans 5 days
Delta
Delta
PHL
MDW
3h 39m
1 stop
MDW
PHL
3h 36m
1 stop
Depart: Sat May 30 2015 Return: Wed Jun 3 2015 Trip spans 5 days
Delta
Delta
JFK
MDW
6h 15m
1 stop
MDW
JFK
4h 26m
1 stop
Depart: Tue Apr 21 2015 Return: Wed Apr 29 2015 Trip spans 9 days
Delta
Delta
EWR
MDW
4h 15m
1 stop
MDW
EWR
4h 39m
1 stop
Depart: Tue Sep 15 2015 Return: Wed Sep 16 2015 Trip spans 2 days
Delta
Delta
CLE
MDW
5h 04m
1 stop
MDW
CLE
4h 17m
1 stop
Depart: Wed May 27 2015 Return: Sun May 31 2015 Trip spans 5 days
Delta
Delta
PHX
MDW
5h 28m
1 stop
MDW
PHX
5h 50m
1 stop
Depart: Sat Aug 22 2015 Return: Sat Aug 29 2015 Trip spans 8 days
Delta
Delta
CMH
MDW
5h 34m
1 stop
MDW
CMH
2h 43m
1 stop
Depart: Tue May 26 2015 Return: Thu May 28 2015 Trip spans 3 days
Delta
Delta
OMA
MDW
4h 18m
1 stop
MDW
OMA
4h 20m
1 stop
Airports
Origin

New York
$196
Detroit
$167
Fort Lauderdale
$184
Cleveland
$202
Miami
$184
Omaha
$232
West Palm Beach
$184
Minneapolis
$81
New Orleans
$184
Columbus
$206
Phoenix
$204
Newark
$198
Dallas
only $184
only $184
Tampa
$184
Philadelphia
$194
Houston
only $184
only $184
Boston
$184
Pittsburgh
$186
Destination

Chicago
$81