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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 May 19 2015 Return: Wed May 20 2015 Trip spans 2 days
Delta
Delta
MDW
5:25a
ORL
9:47a
4h 22m
1 stop
ORL
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Wed May 20 2015 Return: Sat May 23 2015 Trip spans 4 days
Delta
Delta
MDW
12:34p
ORL
5:29p
4h 55m
1 stop
ORL
11:15a
MDW
4:57p
5h 42m
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
6:00a
ORL
10:30a
4h 30m
1 stop
ORL
9:20a
MDW
2:22p
5h 02m
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
12:20p
MDW
7:10p
6h 50m
1 stop
Depart: Tue Jun 2 2015 Return: Sat Jun 6 2015 Trip spans 5 days
Delta
Delta
MDW
5:25a
ORL
9:47a
4h 22m
1 stop
ORL
1:15a
MDW
8:25a
7h 10m
1 stop
Depart: Wed Jun 3 2015 Return: Sat Jun 6 2015 Trip spans 4 days
Delta
Delta
MDW
6:00a
ORL
10:30a
4h 30m
1 stop
ORL
9:30a
MDW
2:28p
4h 58m
1 stop
Depart: Sat Jun 6 2015 Return: Tue Jun 9 2015 Trip spans 4 days
Delta
Delta
MDW
2:05p
ORL
6:27p
4h 22m
1 stop
ORL
9:30a
MDW
2:30p
5h 00m
1 stop
Depart: Tue Jun 9 2015 Return: Wed Jun 10 2015 Trip spans 2 days
Delta
Delta
MDW
2:05p
ORL
6:29p
4h 24m
1 stop
ORL
4:20a
MDW
8:54a
4h 34m
1 stop
Depart: Wed Jun 10 2015 Return: Tue Jun 16 2015 Trip spans 7 days
Delta
Delta
MDW
3:10a
ORL
8:23a
5h 13m
1 stop
ORL
7:20a
MDW
12:09p
4h 49m
1 stop
Depart: Tue Jun 16 2015 Return: Tue Jun 23 2015 Trip spans 8 days
Delta
Delta
MDW
5:47a
ORL
10:44a
4h 57m
1 stop
ORL
12:35p
MDW
5:25p
4h 50m
1 stop
Depart: Wed Jun 17 2015 Return: Tue Jun 23 2015 Trip spans 7 days
Delta
Delta
MDW
2:05p
ORL
7:38p
5h 33m
1 stop
ORL
12:35p
MDW
5:25p
4h 50m
1 stop
Depart: Tue Jun 23 2015 Return: Tue Jun 30 2015 Trip spans 8 days
Delta
Delta
MDW
3:28p
ORL
7:38p
4h 10m
1 stop
ORL
12:35p
MDW
5:22p
4h 47m
1 stop
Depart: Wed Jun 24 2015 Return: Wed Jul 1 2015 Trip spans 8 days
Delta
Delta
MDW
5:47a
ORL
10:44a
4h 57m
1 stop
ORL
2:30p
MDW
7:14p
4h 44m
1 stop
Depart: Tue Jun 30 2015 Return: Wed Jul 1 2015 Trip spans 2 days
Delta
Delta
MDW
9:50a
ORL
2:43p
4h 53m
1 stop
ORL
2:30p
MDW
7:14p
4h 44m
1 stop
Depart: Wed Jul 1 2015 Return: Sat Jul 4 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
ORL
6:30a
4h 30m
1 stop
ORL
2:30p
MDW
7:12p
4h 42m
1 stop
Depart: Sat Jul 4 2015 Return: Tue Jul 7 2015 Trip spans 4 days
Delta
Delta
MDW
4:30a
ORL
10:35a
6h 05m
1 stop
ORL
1:30p
MDW
7:14p
5h 44m
1 stop
Depart: Tue Jul 7 2015 Return: Wed Jul 8 2015 Trip spans 2 days
Delta
Delta
MDW
3:28p
ORL
7:37p
4h 09m
1 stop
ORL
2:20a
MDW
6:20a
4h 00m
1 stop
Depart: Wed Sep 2 2015 Return: Sun Sep 6 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MDW
4:00a
ORL
7:08a
27h 08m
1 stop
ORL
9:00a
MDW
5:45p
8h 45m
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
2879 6:00 am 9:45 am May 25 - May 25
845 6:00 am 9:45 am May 26 - Jun 5
845 6:00 am 9:45 am Apr 26 - May 22
3017 6:30 am 10:15 am May 24 - May 24
2729 6:35 am 10:15 am May 23 - May 23
1839 6:45 am 10:25 am Apr 25 - May 16
1839 6:45 am 10:25 am May 30 - May 30
4639 7:05 am 10:35 am Apr 26 - Jun 5
1768 7:20 am 10:50 am May 23 - May 23
2727 7:20 am 10:50 am May 30 - Jun 6
2727 7:20 am 10:50 am Apr 25 - May 16
2474 8:20 am 11:55 am May 2 - May 16
2474 8:20 am 11:55 am May 30 - May 30
2738 8:30 am 12:05 pm May 23 - May 23
3305 10:20 am 1:55 pm Apr 25 - May 30
2671 10:35 am 2:10 pm May 26 - Jun 5
2671 10:35 am 2:10 pm Apr 26 - May 22
3125 10:35 am 2:10 pm May 24 - May 24
3644 10:35 am 2:10 pm May 25 - May 25
1114 12:20 pm 3:55 pm May 30 - May 30
1114 12:20 pm 3:55 pm Apr 25 - May 16
34 12:20 pm 3:55 pm May 23 - May 23
3753 1:15 pm 4:55 pm Apr 25 - May 30
1979 1:20 pm 5:00 pm Apr 26 - May 22
1979 1:20 pm 5:00 pm May 26 - Jun 5
866 1:20 pm 5:00 pm May 25 - May 25
866 1:20 pm 5:00 pm May 24 - May 24
1603 3:55 pm 7:30 pm Apr 25 - May 16
1603 3:55 pm 7:30 pm May 30 - Jun 6
1634 3:55 pm 7:30 pm May 23 - May 23
4589 4:55 pm 8:30 pm Apr 26 - May 22
4589 4:55 pm 8:30 pm May 26 - Jun 5
2655 5:00 pm 8:35 pm May 23 - May 23
299 5:00 pm 8:35 pm May 24 - May 24
958 5:00 pm 8:35 pm Apr 25 - May 16
958 5:00 pm 8:35 pm May 30 - Jun 6
994 5:10 pm 8:45 pm May 25 - May 25
2130 5:50 pm 9:30 pm May 25 - May 25
2325 5:50 pm 9:30 pm May 24 - May 24
3702 5:50 pm 9:30 pm May 31 - May 31
3702 5:50 pm 9:30 pm May 10 - May 17
540 5:50 pm 9:30 pm May 26 - Jun 5
540 5:50 pm 9:30 pm Apr 27 - May 22
1716 6:25 pm 10:00 pm May 9 - May 16
1716 6:25 pm 10:00 pm May 30 - Jun 6
552 8:35 pm 12:05 am May 25 - May 25
594 9:20 pm 12:50 am May 26 - Jun 5
594 9:20 pm 12:50 am Apr 26 - May 22
594 9:25 pm 12:55 am May 24 - May 24
Airports
Origin

Chicago
$286
Destination

Orlando
$286