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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago Midway to Orlando All airports

(Round-trip)
Depart: Mon Nov 16 2015 Return: Wed Nov 25 2015 Trip spans 10 days
Southwest
Southwest
MDW
8:35a
MCO
11:10a
2h 35m
nonstop
MCO
2:10a
MDW
5:05a
2h 55m
nonstop
Depart: Mon Aug 3 2015 Return: Wed Aug 5 2015 Trip spans 3 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
8:05a
MDW
4:01p
7h 56m
1 stop
Depart: Tue Aug 4 2015 Return: Tue Aug 18 2015 Trip spans 15 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
8:25a
MDW
3:57p
7h 32m
1 stop
Depart: Wed Aug 5 2015 Return: Mon Aug 10 2015 Trip spans 6 days
Delta
Delta
MDW
8:25a
MCO
12:58p
4h 33m
1 stop
MCO
10:23a
MDW
6:35p
8h 12m
1 stop
Depart: Thu Aug 6 2015 Return: Wed Aug 12 2015 Trip spans 7 days
Delta
Delta
MDW
2:30a
MCO
8:19a
5h 49m
1 stop
MCO
11:30a
MDW
7:14p
7h 44m
1 stop
Depart: Mon Aug 10 2015 Return: Tue Aug 18 2015 Trip spans 9 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 11 2015 Return: Wed Aug 12 2015 Trip spans 2 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
5:30a
MDW
10:18a
4h 48m
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
10:30a
MDW
3:57p
5h 27m
1 stop
Depart: Thu Aug 13 2015 Return: Tue Aug 18 2015 Trip spans 6 days
Delta
Delta
MDW
3:05a
MCO
8:21a
5h 16m
1 stop
MCO
9:30a
MDW
3:57p
6h 27m
1 stop
Depart: Fri Aug 14 2015 Return: Tue Aug 18 2015 Trip spans 5 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
9:30a
MDW
2:22p
4h 52m
1 stop
Depart: Sat Aug 15 2015 Return: Wed Aug 19 2015 Trip spans 5 days
Delta
Delta
MDW
2:14p
MCO
7:19p
5h 05m
1 stop
MCO
2:30p
MDW
7:12p
4h 42m
1 stop
Depart: Mon Aug 17 2015 Return: Sun Aug 23 2015 Trip spans 7 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
1:20a
MDW
6:12a
4h 52m
1 stop
Depart: Tue Aug 18 2015 Return: Wed Aug 19 2015 Trip spans 2 days
Delta
Delta
MDW
11:28a
MCO
3:43p
4h 15m
1 stop
MCO
2:30p
MDW
7:12p
4h 42m
1 stop
Depart: Wed Aug 19 2015 Return: Fri Aug 21 2015 Trip spans 3 days
Delta
Delta
MDW
5:55a
MCO
10:36a
4h 41m
1 stop
MCO
4:20a
MDW
9:23a
5h 03m
1 stop
Depart: Thu Aug 20 2015 Return: Wed Aug 26 2015 Trip spans 7 days
Delta
Delta
MDW
5:55a
MCO
10:36a
4h 41m
1 stop
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
Depart: Sat Aug 22 2015 Return: Tue Aug 25 2015 Trip spans 4 days
Delta
Delta
MDW
8:31a
MCO
3:24p
6h 53m
1 stop
MCO
3:20a
MDW
8:44a
5h 24m
1 stop
Depart: Mon Aug 24 2015 Return: Tue Aug 25 2015 Trip spans 2 days
Delta
Delta
MDW
8:31a
MCO
12:56p
4h 25m
1 stop
MCO
9:30a
MDW
3:57p
6h 27m
1 stop
Depart: Tue Aug 25 2015 Return: Wed Aug 26 2015 Trip spans 2 days
Delta
Delta
MDW
11:28a
MCO
5:23p
5h 55m
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
5:55a
MCO
11:35a
5h 40m
1 stop
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
Depart: Thu Aug 27 2015 Return: Sat Aug 29 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
MCO
7:26a
5h 26m
1 stop
MCO
8:05a
MDW
1:43p
5h 38m
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 Aug 1 - Aug 8
1891 6:00 am 9:35 am Jul 28 - Aug 7
6366 6:05 am 9:35 am Aug 9 - Sep 4
1370 6:50 am 10:25 am Aug 1 - Aug 8
3028 7:00 am 10:35 am Jul 28 - Aug 7
4519 7:10 am 10:40 am Aug 15 - Aug 29
5316 7:10 am 10:40 am Sep 5 - Sep 5
2312 7:35 am 11:05 am Aug 1 - Aug 8
1627 8:00 am 11:30 am Sep 5 - Sep 5
3886 8:00 am 11:30 am Aug 15 - Aug 29
1463 8:15 am 11:45 am Aug 9 - Aug 30
3017 8:15 am 11:45 am Aug 10 - Sep 10
985 8:15 am 11:45 am Sep 6 - Sep 6
1617 9:15 am 12:45 pm Jul 28 - Aug 7
3166 9:20 am 12:50 pm Sep 6 - Sep 6
1930 9:25 am 12:55 pm Sep 5 - Sep 5
4440 9:25 am 12:55 pm Aug 15 - Aug 29
2058 9:50 am 1:20 pm Aug 1 - Aug 8
5221 10:25 am 1:55 pm Sep 5 - Sep 5
924 10:25 am 1:55 pm Aug 15 - Aug 29
2258 10:40 am 2:10 pm Aug 3 - Aug 7
4378 11:15 am 2:50 pm Aug 1 - Aug 8
669 11:40 am 3:10 pm Aug 9 - Sep 6
1639 12:05 pm 3:40 pm Aug 15 - Aug 29
1845 12:05 pm 3:40 pm Sep 5 - Sep 5
1636 12:10 pm 3:45 pm Jul 28 - Aug 7
1002 1:20 pm 5:00 pm Sep 5 - Sep 5
4745 1:20 pm 5:00 pm Aug 15 - Aug 29
1807 1:30 pm 5:15 pm Aug 8 - Aug 8
4930 1:35 pm 5:25 pm Jul 28 - Aug 7
660 1:35 pm 5:15 pm Aug 23 - Sep 4
660 1:35 pm 5:15 pm Aug 16 - Aug 21
660 1:35 pm 5:15 pm Aug 9 - Aug 14
3079 1:40 pm 5:20 pm Sep 6 - Sep 6
1101 3:00 pm 6:35 pm Sep 6 - Sep 6
2887 3:00 pm 6:35 pm Aug 31 - Sep 4
2887 3:00 pm 6:35 pm Aug 10 - Aug 28
3362 3:05 pm 6:40 pm Aug 9 - Aug 30
1755 3:15 pm 6:50 pm Aug 15 - Aug 29
1515 3:40 pm 7:20 pm Jul 28 - Aug 7
2040 3:50 pm 7:30 pm Aug 1 - Aug 8
2159 4:20 pm 7:55 pm Sep 6 - Sep 6
2159 4:20 pm 7:55 pm Aug 9 - Aug 14
2159 4:20 pm 7:55 pm Aug 16 - Sep 4
2065 4:30 pm 8:10 pm Aug 1 - Aug 8
4763 4:50 pm 8:25 pm Aug 15 - Aug 15
4763 4:50 pm 8:25 pm Aug 22 - Aug 29
1318 5:15 pm 9:00 pm Aug 1 - Aug 8
313 5:25 pm 9:00 pm Jul 28 - Aug 7
4249 6:00 pm 9:45 pm Aug 1 - Aug 8
2693 6:10 pm 9:45 pm Sep 5 - Sep 5
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 31 - Aug 7
4612 9:15 pm 12:50 am Aug 1 - Aug 8
Airports
Origin

Chicago
$155
Destination

Orlando
$155