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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: Sat Feb 21 2015 Return: Tue Feb 24 2015 Trip spans 4 days
Delta
Delta
MDW
7:30a
ORL
2:37p
7h 07m
1 stop
ORL
12:20a
MDW
5:11a
4h 51m
1 stop
Depart: Wed Feb 25 2015 Return: Sat Feb 28 2015 Trip spans 4 days
Delta
Delta
MDW
12:59p
ORL
6:23p
5h 24m
1 stop
ORL
12:30p
MDW
5:44p
5h 14m
1 stop
Depart: Tue Mar 3 2015 Return: Wed Mar 4 2015 Trip spans 2 days
Delta
Delta
MDW
1:00a
ORL
6:26a
5h 26m
1 stop
ORL
5:20a
MDW
9:36a
4h 16m
1 stop
Depart: Tue Mar 10 2015 Return: Tue Mar 17 2015 Trip spans 8 days
Delta
Delta
MDW
10:11a
ORL
2:27p
4h 16m
1 stop
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
Depart: Wed Mar 11 2015 Return: Tue Mar 17 2015 Trip spans 7 days
Delta
Delta
MDW
10:11a
ORL
3:26p
5h 15m
1 stop
ORL
1:30p
MDW
7:15p
5h 45m
1 stop
Depart: Tue Mar 17 2015 Return: Wed Mar 18 2015 Trip spans 2 days
Delta
Delta
MDW
2:00a
ORL
6:20a
4h 20m
1 stop
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
Depart: Wed Mar 18 2015 Return: Tue Mar 24 2015 Trip spans 7 days
Delta
Delta
MDW
2:00a
ORL
6:20a
4h 20m
1 stop
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
Depart: Tue Mar 24 2015 Return: Wed Mar 25 2015 Trip spans 2 days
Delta
Delta
MDW
10:11a
ORL
2:27p
4h 16m
1 stop
ORL
6:20a
MDW
10:36a
4h 16m
1 stop
Depart: Wed Mar 25 2015 Return: Tue Mar 31 2015 Trip spans 7 days
Delta
Delta
MDW
10:11a
ORL
2:27p
4h 16m
1 stop
ORL
4:30a
MDW
8:46a
4h 16m
1 stop
Depart: Tue Mar 31 2015 Return: Wed Apr 8 2015 Trip spans 9 days
Delta
Delta
MDW
2:00a
ORL
6:20a
4h 20m
1 stop
ORL
1:20a
MDW
6:04a
4h 44m
1 stop
Depart: Wed Apr 8 2015 Return: Tue Apr 14 2015 Trip spans 7 days
Delta
Delta
MDW
8:30a
ORL
12:22p
3h 52m
1 stop
ORL
6:30a
MDW
11:42a
5h 12m
1 stop
Depart: Sat Apr 11 2015 Return: Tue Apr 14 2015 Trip spans 4 days
Delta
Delta
MDW
8:15a
ORL
12:22p
4h 07m
1 stop
ORL
1:20a
MDW
6:04a
4h 44m
1 stop
Depart: Tue Apr 14 2015 Return: Sat Apr 25 2015 Trip spans 12 days
Delta
Delta
MDW
8:30a
ORL
12:22p
3h 52m
1 stop
ORL
4:30a
MDW
8:49a
4h 19m
1 stop
Depart: Wed Apr 15 2015 Return: Sat Apr 25 2015 Trip spans 11 days
Delta
Delta
MDW
9:50a
ORL
2:22p
4h 32m
1 stop
ORL
4:30a
MDW
8:49a
4h 19m
1 stop
Depart: Sat Apr 18 2015 Return: Sat Apr 25 2015 Trip spans 8 days
Delta
Delta
MDW
8:10a
ORL
2:52p
6h 42m
1 stop
ORL
4:30a
MDW
8:49a
4h 19m
1 stop
Depart: Tue May 5 2015 Return: Wed May 6 2015 Trip spans 2 days
Delta
Delta
MDW
8:30a
ORL
12:22p
3h 52m
1 stop
ORL
3:20a
MDW
8:49a
5h 29m
1 stop
Depart: Wed May 6 2015 Return: Tue May 12 2015 Trip spans 7 days
Delta
Delta
MDW
8:40a
ORL
1:11p
4h 31m
1 stop
ORL
5:30a
MDW
10:12a
4h 42m
1 stop
Depart: Mon Feb 16 2015 Return: Tue Feb 24 2015 Trip spans 9 days
Delta
Delta
MDW
10:19a
ORL
2:28p
4h 09m
1 stop
ORL
12:20a
MDW
5:11a
4h 51m
1 stop
Depart: Tue Feb 17 2015 Return: Tue Feb 24 2015 Trip spans 8 days
Delta
Delta
MDW
9:06a
ORL
1:26p
4h 20m
1 stop
ORL
12:20a
MDW
5:11a
4h 51m
1 stop
Depart: Fri Apr 3 2015 Return: Fri Apr 10 2015 Trip spans 8 days
Sun Country Air
Sun Country Air
MDW
5:20a
ORL
2:58p
9h 38m
1 stop
ORL
4:45p
MDW
6:40a
61h 55m
1 stop
Change your search
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
4826 5:55 am 9:35 am Jan 29 - Mar 6
2788 6:00 am 9:40 am Jan 31 - Feb 28
4293 6:00 am 9:45 am Mar 8 - Apr 7
2645 6:25 am 10:00 am Mar 7 - Mar 7
3117 7:05 am 10:40 am Mar 8 - Mar 27
3246 7:15 am 10:55 am Jan 31 - Feb 28
266 7:55 am 11:30 am Mar 7 - Mar 7
3187 8:10 am 11:45 am Feb 14 - Feb 28
3187 8:10 am 11:45 am Jan 31 - Feb 7
3830 8:30 am 12:05 pm Mar 8 - Apr 5
3830 8:30 am 12:05 pm Mar 9 - Apr 6
2647 9:40 am 1:20 pm Mar 7 - Mar 7
2208 9:50 am 1:30 pm Feb 1 - Mar 1
561 9:50 am 1:30 pm Jan 29 - Mar 6
2404 10:10 am 1:40 pm Mar 9 - Apr 6
4076 10:10 am 1:40 pm Mar 8 - Apr 5
3491 10:20 am 2:00 pm Jan 31 - Feb 28
430 10:20 am 1:55 pm Jan 29 - Mar 6
430 10:20 am 1:55 pm Feb 1 - Mar 1
1503 10:55 am 2:25 pm Mar 7 - Mar 7
2839 11:55 am 3:25 pm Mar 7 - Mar 7
1166 12:30 pm 4:05 pm Feb 2 - Mar 6
4157 12:30 pm 4:05 pm Feb 8 - Mar 1
1671 12:45 pm 4:15 pm Mar 7 - Mar 7
2341 1:00 pm 4:35 pm Mar 9 - Mar 9
2341 1:00 pm 4:35 pm Mar 8 - Mar 13
2678 1:10 pm 4:45 pm Jan 31 - Feb 28
1777 2:40 pm 6:10 pm Mar 7 - Mar 7
4649 3:10 pm 6:50 pm Mar 8 - Apr 6
3143 3:30 pm 7:00 pm Jan 31 - Feb 28
562 3:45 pm 7:20 pm Jan 29 - Feb 9
562 3:45 pm 7:20 pm Feb 13 - Mar 2
562 3:45 pm 7:20 pm Feb 10 - Feb 15
562 3:45 pm 7:20 pm Mar 3 - Mar 5
562 3:45 pm 7:20 pm Feb 22 - Mar 1
562 3:45 pm 7:20 pm Mar 6 - Mar 6
562 3:45 pm 7:20 pm Feb 1 - Feb 8
2530 4:30 pm 8:00 pm Mar 7 - Mar 7
341 5:05 pm 8:40 pm Mar 7 - Mar 7
590 5:20 pm 9:00 pm Jan 29 - Mar 6
3561 5:30 pm 9:00 pm Jan 31 - Feb 28
1603 6:00 pm 9:30 pm Mar 7 - Mar 7
1159 6:05 pm 9:35 pm Mar 8 - Mar 20
2163 6:25 pm 9:55 pm Feb 8 - Mar 6
494 7:40 pm 11:10 pm Mar 7 - Mar 7
323 8:05 pm 11:30 pm Mar 8 - Apr 5
323 8:05 pm 11:30 pm Mar 9 - Apr 6
2655 9:00 pm 12:25 am Mar 7 - Mar 7
1788 9:25 pm 12:50 am Mar 8 - Mar 15
Airports
Origin

Chicago
$236
Destination

Orlando
$236