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Find Flight Deals from Orlando All airports to Chicago Midway (ORL - MDW)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Orlando All airports to Chicago Midway

(Round-trip)
Depart: Wed Feb 18 2015 Return: Tue Feb 24 2015 Trip spans 7 days
Delta
Delta
ORL
12:20a
MDW
5:11a
4h 51m
1 stop
MDW
10:19a
ORL
2:28p
4h 09m
1 stop
Depart: Wed Feb 25 2015 Return: Wed Mar 4 2015 Trip spans 8 days
Delta
Delta
ORL
12:20a
MDW
5:11a
4h 51m
1 stop
MDW
9:11a
ORL
2:26p
5h 15m
1 stop
Depart: Tue Mar 10 2015 Return: Tue Mar 17 2015 Trip spans 8 days
Delta
Delta
ORL
4:30a
MDW
8:46a
4h 16m
1 stop
MDW
10:11a
ORL
2:27p
4h 16m
1 stop
Depart: Wed Mar 11 2015 Return: Tue Mar 17 2015 Trip spans 7 days
Delta
Delta
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
MDW
10:11a
ORL
2:27p
4h 16m
1 stop
Depart: Tue Mar 17 2015 Return: Wed Mar 18 2015 Trip spans 2 days
Delta
Delta
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
MDW
2:00a
ORL
6:20a
4h 20m
1 stop
Depart: Tue Mar 24 2015 Return: Tue Mar 31 2015 Trip spans 8 days
Delta
Delta
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
MDW
2:00a
ORL
6:20a
4h 20m
1 stop
Depart: Wed Mar 25 2015 Return: Tue Mar 31 2015 Trip spans 7 days
Delta
Delta
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
MDW
2:00a
ORL
6:20a
4h 20m
1 stop
Depart: Tue Mar 31 2015 Return: Wed Apr 8 2015 Trip spans 9 days
Delta
Delta
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
MDW
8:30a
ORL
12:22p
3h 52m
1 stop
Depart: Wed Apr 1 2015 Return: Wed Apr 8 2015 Trip spans 8 days
Delta
Delta
ORL
4:30a
MDW
8:44a
4h 14m
1 stop
MDW
8:30a
ORL
12:22p
3h 52m
1 stop
Depart: Tue Apr 7 2015 Return: Sat Apr 11 2015 Trip spans 5 days
Delta
Delta
ORL
10:30a
MDW
4:54p
6h 24m
1 stop
MDW
8:15a
ORL
2:22p
6h 07m
1 stop
Depart: Wed Apr 15 2015 Return: Tue Apr 21 2015 Trip spans 7 days
Delta
Delta
ORL
5:30a
MDW
10:12a
4h 42m
1 stop
MDW
12:45p
ORL
5:26p
4h 41m
1 stop
Depart: Tue Apr 21 2015 Return: Wed Apr 29 2015 Trip spans 9 days
Delta
Delta
ORL
1:30p
MDW
6:27p
4h 57m
1 stop
MDW
9:50a
ORL
2:22p
4h 32m
1 stop
Depart: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
Delta
Delta
ORL
2:20p
MDW
6:55p
4h 35m
1 stop
MDW
7:05a
ORL
12:14p
5h 09m
1 stop
Depart: Sat Apr 25 2015 Return: Tue Apr 28 2015 Trip spans 4 days
Delta
Delta
ORL
4:30a
MDW
8:49a
4h 19m
1 stop
MDW
8:30a
ORL
12:22p
3h 52m
1 stop
Depart: Wed Feb 11 2015 Return: Tue Mar 10 2015 Trip spans 27 days
Delta
Delta
ORL
2:20a
MDW
7:29a
5h 09m
1 stop
MDW
5:51a
ORL
10:30a
4h 39m
1 stop
Depart: Thu Feb 12 2015 Return: Tue Mar 10 2015 Trip spans 26 days
Delta
Delta
ORL
3:30a
MDW
9:05a
5h 35m
1 stop
MDW
10:11a
ORL
2:27p
4h 16m
1 stop
Depart: Fri Feb 13 2015 Return: Tue Mar 10 2015 Trip spans 25 days
Delta
Delta
ORL
12:20a
MDW
5:11a
4h 51m
1 stop
MDW
2:35p
ORL
7:08p
4h 33m
1 stop
Depart: Sat Feb 28 2015 Return: Mon Mar 2 2015 Trip spans 3 days
Delta
Delta
ORL
12:30p
MDW
5:44p
5h 14m
1 stop
MDW
10:37a
ORL
3:25p
4h 48m
1 stop
Depart: Wed Mar 4 2015 Return: Mon Mar 9 2015 Trip spans 5 days
Delta
Delta
ORL
1:20p
MDW
5:55p
4h 35m
1 stop
MDW
2:00a
ORL
6:20a
4h 20m
1 stop
Depart: Thu Mar 5 2015 Return: Tue Mar 10 2015 Trip spans 5 days
Delta
Delta
ORL
5:20a
MDW
9:36a
4h 16m
1 stop
MDW
11:37a
ORL
4:25p
4h 48m
1 stop
Change your search
Select an airline:  Southwest
Direct flights ORL to MDW on Southwest
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1624 6:50 am 8:55 am Mar 7 - Mar 7
2442 7:20 am 9:10 am Mar 7 - Mar 7
1621 8:00 am 9:55 am Jan 27 - Mar 6
3421 8:45 am 10:40 am Jan 31 - Feb 28
139 9:00 am 10:55 am Jan 27 - Mar 6
114 9:40 am 11:30 am Mar 7 - Mar 7
4855 10:55 am 12:50 pm Mar 7 - Mar 7
979 11:00 am 12:50 pm Jan 27 - Mar 6
979 11:00 am 12:50 pm Feb 1 - Mar 1
2464 11:20 am 1:10 pm Jan 31 - Feb 28
493 11:45 am 1:40 pm Mar 7 - Mar 7
1957 1:10 pm 3:00 pm Mar 7 - Mar 7
538 2:00 pm 3:50 pm Jan 27 - Feb 20
538 2:00 pm 3:50 pm Feb 8 - Mar 1
538 2:00 pm 3:50 pm Feb 23 - Feb 27
538 2:00 pm 3:50 pm Mar 2 - Mar 6
181 2:05 pm 3:55 pm Mar 7 - Mar 7
3113 2:10 pm 4:00 pm Feb 21 - Feb 21
3113 2:10 pm 4:00 pm Feb 28 - Feb 28
3113 2:10 pm 4:00 pm Feb 14 - Feb 14
3113 2:10 pm 4:00 pm Jan 31 - Feb 7
223 3:20 pm 5:10 pm Mar 7 - Mar 7
555 3:25 pm 5:15 pm Mar 1 - Mar 6
555 3:25 pm 5:15 pm Feb 15 - Feb 20
555 3:25 pm 5:15 pm Feb 22 - Feb 27
555 3:25 pm 5:15 pm Feb 2 - Feb 6
555 3:25 pm 5:15 pm Feb 8 - Feb 13
1273 4:20 pm 6:10 pm Mar 7 - Mar 7
3699 4:30 pm 6:20 pm Jan 31 - Feb 28
284 5:00 pm 6:50 pm Mar 7 - Mar 7
871 5:05 pm 7:00 pm Feb 1 - Mar 1
871 5:05 pm 7:00 pm Jan 27 - Mar 6
3600 6:10 pm 8:05 pm Jan 31 - Feb 28
185 6:25 pm 8:15 pm Mar 7 - Mar 7
3887 7:00 pm 8:50 pm Jan 31 - Feb 28
419 7:00 pm 8:55 pm Mar 7 - Mar 7
3931 7:50 pm 9:40 pm Jan 27 - Mar 6
3790 9:00 pm 10:50 pm Jan 31 - Feb 28
1386 10:00 pm 11:50 pm Mar 7 - Mar 7
Airports
Origin

Orlando
$236
Destination

Chicago
$236
Airlines