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Find Deals on Flights 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: Thu Jul 9 2015 Return: Mon Jul 20 2015 Trip spans 12 days
Delta
Delta
MDW
8:25a
MCO
12:58p
4h 33m
1 stop
MCO
1:30p
MDW
7:14p
5h 44m
1 stop
Depart: Tue Jul 14 2015 Return: Tue Jul 21 2015 Trip spans 8 days
Delta
Delta
MDW
8:25a
MCO
3:20p
6h 55m
1 stop
MCO
8:02a
MDW
2:53p
6h 51m
1 stop
Depart: Tue Jul 21 2015 Return: Tue Jul 28 2015 Trip spans 8 days
Delta
Delta
MDW
9:53a
MCO
3:44p
5h 51m
1 stop
MCO
4:20a
MDW
9:23a
5h 03m
1 stop
Depart: Tue Jul 28 2015 Return: Sun Aug 2 2015 Trip spans 6 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
1:20a
MDW
6:20a
5h 00m
1 stop
Depart: Wed Jul 29 2015 Return: Mon Aug 24 2015 Trip spans 27 days
Delta
Delta
MDW
3:00a
MCO
9:59a
6h 59m
1 stop
MCO
4:20a
MDW
10:05a
5h 45m
1 stop
Depart: Tue Aug 4 2015 Return: Tue Aug 11 2015 Trip spans 8 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
11:30a
MDW
7:14p
7h 44m
1 stop
Depart: Wed Aug 5 2015 Return: Tue Aug 11 2015 Trip spans 7 days
Delta
Delta
MDW
5:09a
MCO
12:21p
7h 12m
1 stop
MCO
11:30a
MDW
5:20p
5h 50m
1 stop
Depart: Thu Aug 6 2015 Return: Wed Aug 12 2015 Trip spans 7 days
Delta
Delta
MDW
5:07a
MCO
9:59a
4h 52m
1 stop
MCO
5:30a
MDW
12:07p
6h 37m
1 stop
Depart: Tue Aug 11 2015 Return: Tue Aug 18 2015 Trip spans 8 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
7:53a
MDW
12:58p
5h 05m
1 stop
Depart: Wed Aug 12 2015 Return: Tue Aug 18 2015 Trip spans 7 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
Depart: Thu Aug 13 2015 Return: Sun Aug 23 2015 Trip spans 11 days
Delta
Delta
MDW
2:30a
MCO
8:19a
5h 49m
1 stop
MCO
2:20a
MDW
6:12a
3h 52m
1 stop
Depart: Mon Aug 17 2015 Return: Wed Aug 19 2015 Trip spans 3 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
2:30p
MDW
7:12p
4h 42m
1 stop
Depart: Tue Aug 18 2015 Return: Wed Aug 19 2015 Trip spans 2 days
Delta
Delta
MDW
5:55a
MCO
10:36a
4h 41m
1 stop
MCO
9:30a
MDW
2:22p
4h 52m
1 stop
Depart: Wed Aug 19 2015 Return: Sun Aug 23 2015 Trip spans 5 days
Delta
Delta
MDW
3:10a
MCO
9:23a
6h 13m
1 stop
MCO
1:20a
MDW
6:12a
4h 52m
1 stop
Depart: Thu Aug 20 2015 Return: Sun Aug 23 2015 Trip spans 4 days
Delta
Delta
MDW
5:00a
MCO
10:01a
5h 01m
1 stop
MCO
2:20a
MDW
6:12a
3h 52m
1 stop
Depart: Sat Aug 22 2015 Return: Sun Aug 23 2015 Trip spans 2 days
Delta
Delta
MDW
2:00a
MCO
8:20a
6h 20m
1 stop
MCO
2:20a
MDW
6:12a
3h 52m
1 stop
Depart: Mon Aug 24 2015 Return: Wed Aug 26 2015 Trip spans 3 days
Delta
Delta
MDW
1:57p
MCO
6:26p
4h 29m
1 stop
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
Depart: Tue Aug 25 2015 Return: Wed Aug 26 2015 Trip spans 2 days
Delta
Delta
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
MCO
2:20a
MDW
6:12a
3h 52m
1 stop
Depart: Wed Aug 26 2015 Return: Thu Aug 27 2015 Trip spans 2 days
Delta
Delta
MDW
3:10a
MCO
7:26a
4h 16m
1 stop
MCO
2:20a
MDW
6:12a
3h 52m
1 stop
Depart: Thu Aug 27 2015 Return: Sun Aug 30 2015 Trip spans 4 days
Delta
Delta
MDW
11:28a
MCO
3:43p
4h 15m
1 stop
MCO
4:20a
MDW
10:05a
5h 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
2644 5:35 am 9:05 am Jul 11 - Aug 8
1891 6:00 am 9:35 am Jul 10 - Aug 7
6366 6:05 am 9:35 am Aug 9 - Sep 4
1370 6:50 am 10:25 am Jul 11 - Aug 8
3028 7:00 am 10:35 am Jun 28 - Aug 2
3028 7:00 am 10:35 am Jul 10 - Aug 7
2312 7:35 am 11:05 am Jul 11 - Aug 8
1463 8:15 am 11:45 am Aug 9 - Aug 30
3017 8:15 am 11:45 am Aug 10 - Sep 10
4068 9:00 am 12:30 pm Jun 28 - Aug 2
1617 9:15 am 12:45 pm Jul 10 - Aug 7
2058 9:50 am 1:20 pm Jul 11 - Aug 8
2258 10:40 am 2:10 pm Jun 29 - Jul 31
2258 10:40 am 2:10 pm Aug 3 - Aug 7
4116 10:40 am 2:10 pm Jun 28 - Aug 2
4378 11:15 am 2:50 pm Jul 11 - Aug 8
669 11:40 am 3:10 pm Aug 9 - Sep 6
1636 12:10 pm 3:45 pm Jul 10 - Aug 7
612 12:10 pm 3:45 pm Jun 28 - Aug 2
1807 1:30 pm 5:15 pm Jul 11 - Aug 1
1807 1:30 pm 5:15 pm Aug 8 - Aug 8
4930 1:35 pm 5:25 pm Jun 28 - Aug 7
660 1:35 pm 5:15 pm Aug 9 - Aug 14
2887 3:00 pm 6:35 pm Aug 10 - Aug 14
3362 3:05 pm 6:40 pm Aug 9 - Aug 30
1515 3:40 pm 7:20 pm Jul 5 - Aug 7
2040 3:50 pm 7:30 pm Jul 11 - Aug 8
2159 4:20 pm 7:55 pm Aug 9 - Sep 4
2065 4:30 pm 8:10 pm Jul 11 - Aug 8
1318 5:15 pm 9:00 pm Jul 11 - Aug 8
313 5:25 pm 9:00 pm Jul 10 - Aug 7
4249 6:00 pm 9:45 pm Jul 11 - Aug 8
2109 7:00 pm 10:30 pm Aug 9 - Aug 30
2209 7:00 pm 10:30 pm Aug 10 - Oct 30
3041 8:35 pm 12:10 am Jul 24 - Aug 7
3041 8:35 pm 12:10 am Jul 10 - Jul 17
4612 9:15 pm 12:50 am Jul 11 - Aug 8
Airports
Origin

Chicago
$185
Destination

Orlando
$185
Airlines