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

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

Book cheap flights from Chicago Midway to Orlando All airports

(Round-trip)
Depart: Tue Apr 21 2015 Return: Wed Apr 22 2015 Trip spans 2 days
Delta
Delta
MDW
10:30a
ORL
2:35p
4h 05m
1 stop
ORL
4:30a
MDW
8:41a
4h 11m
1 stop
Depart: Wed Apr 22 2015 Return: Sat Apr 25 2015 Trip spans 4 days
Delta
Delta
MDW
10:30a
ORL
2:35p
4h 05m
1 stop
ORL
2:20a
MDW
8:40a
6h 20m
1 stop
Depart: Sat Apr 25 2015 Return: Sat May 2 2015 Trip spans 8 days
Delta
Delta
MDW
1:57p
ORL
6:57p
5h 00m
1 stop
ORL
12:25p
MDW
4:56p
4h 31m
1 stop
Depart: Tue Apr 28 2015 Return: Sat May 2 2015 Trip spans 5 days
Delta
Delta
MDW
2:00a
ORL
6:22a
4h 22m
1 stop
ORL
2:20a
MDW
6:21a
4h 01m
1 stop
Depart: Wed Apr 29 2015 Return: Sat May 2 2015 Trip spans 4 days
Delta
Delta
MDW
8:18a
ORL
12:25p
4h 07m
1 stop
ORL
2:20a
MDW
6:21a
4h 01m
1 stop
Depart: Sat May 2 2015 Return: Tue May 5 2015 Trip spans 4 days
Delta
Delta
MDW
8:20a
ORL
12:24p
4h 04m
1 stop
ORL
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Tue May 5 2015 Return: Sat May 9 2015 Trip spans 5 days
Delta
Delta
MDW
2:45a
ORL
8:07a
5h 22m
1 stop
ORL
7:15a
MDW
11:51a
4h 36m
1 stop
Depart: Wed May 6 2015 Return: Sat May 9 2015 Trip spans 4 days
Delta
Delta
MDW
8:22a
ORL
1:29p
5h 07m
1 stop
ORL
4:20a
MDW
8:45a
4h 25m
1 stop
Depart: Sat May 9 2015 Return: Tue May 12 2015 Trip spans 4 days
Delta
Delta
MDW
1:59p
ORL
6:30p
4h 31m
1 stop
ORL
4:15a
MDW
9:15a
5h 00m
1 stop
Depart: Tue May 12 2015 Return: Wed May 13 2015 Trip spans 2 days
Delta
Delta
MDW
10:26a
ORL
2:44p
4h 18m
1 stop
ORL
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Wed May 13 2015 Return: Sat May 16 2015 Trip spans 4 days
Delta
Delta
MDW
8:22a
ORL
1:29p
5h 07m
1 stop
ORL
2:20a
MDW
6:21a
4h 01m
1 stop
Depart: Sat May 16 2015 Return: Tue May 19 2015 Trip spans 4 days
Delta
Delta
MDW
8:20a
ORL
12:24p
4h 04m
1 stop
ORL
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Tue May 19 2015 Return: Sat May 23 2015 Trip spans 5 days
Delta
Delta
MDW
10:26a
ORL
2:44p
4h 18m
1 stop
ORL
12:25p
MDW
4:56p
4h 31m
1 stop
Depart: Wed May 20 2015 Return: Sat May 23 2015 Trip spans 4 days
Delta
Delta
MDW
5:25a
ORL
9:47a
4h 22m
1 stop
ORL
12:25p
MDW
4:56p
4h 31m
1 stop
Depart: Sat May 23 2015 Return: Tue May 26 2015 Trip spans 4 days
Delta
Delta
MDW
1:59p
ORL
6:15p
4h 16m
1 stop
ORL
4:20a
MDW
8:47a
4h 27m
1 stop
Depart: Tue May 26 2015 Return: Wed May 27 2015 Trip spans 2 days
Delta
Delta
MDW
10:26a
ORL
2:44p
4h 18m
1 stop
ORL
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Wed May 27 2015 Return: Sat May 30 2015 Trip spans 4 days
Delta
Delta
MDW
5:25a
ORL
9:47a
4h 22m
1 stop
ORL
2:20a
MDW
6:21a
4h 01m
1 stop
Depart: Sat May 30 2015 Return: Tue Jun 2 2015 Trip spans 4 days
Delta
Delta
MDW
8:20a
ORL
12:24p
4h 04m
1 stop
ORL
4:20a
MDW
8:47a
4h 27m
1 stop
Depart: Tue Jun 2 2015 Return: Tue Jun 9 2015 Trip spans 8 days
Delta
Delta
MDW
10:26a
ORL
2:44p
4h 18m
1 stop
ORL
4:20a
MDW
8:54a
4h 34m
1 stop
Depart: Wed Jun 3 2015 Return: Tue Jun 9 2015 Trip spans 7 days
Delta
Delta
MDW
12:00p
ORL
4:30p
4h 30m
1 stop
ORL
4:20a
MDW
8:54a
4h 34m
1 stop
Select an airline:  Southwest
Direct flights MDW to ORL on Southwest
Flight # Depart MDW Arrive MCO Sun Mon Tue Wed Thu Fri Sat Valid Between
845 6:00 am 9:45 am Apr 8 - May 22
1839 6:45 am 10:25 am Apr 11 - May 16
4639 7:05 am 10:35 am Apr 8 - Jun 5
2727 7:20 am 10:50 am Apr 11 - May 16
2474 8:20 am 11:55 am May 2 - May 16
2474 8:20 am 11:55 am Apr 11 - Apr 25
3305 10:20 am 1:55 pm Apr 11 - May 30
2671 10:35 am 2:10 pm Apr 8 - May 22
1114 12:20 pm 3:55 pm Apr 11 - May 16
3753 1:15 pm 4:55 pm Apr 11 - May 30
1979 1:20 pm 5:00 pm Apr 8 - May 22
1603 3:55 pm 7:30 pm Apr 11 - May 16
4589 4:55 pm 8:30 pm Apr 8 - Apr 10
4589 4:55 pm 8:30 pm Apr 12 - May 22
958 5:00 pm 8:35 pm Apr 11 - May 16
3702 5:50 pm 9:30 pm May 3 - May 3
3702 5:50 pm 9:30 pm Apr 12 - Apr 26
540 5:50 pm 9:30 pm Apr 8 - May 22
1716 6:25 pm 10:00 pm May 9 - May 16
1716 6:25 pm 10:00 pm Apr 11 - May 2
594 9:20 pm 12:50 am Apr 8 - May 22
Airports
Origin

Chicago
$286
Destination

Orlando
$286
Airlines