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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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 Sep 8 2015 Return: Wed Sep 9 2015 Trip spans 2 days
Delta
Delta
MDW
12:35p
MCO
5:59p
5h 24m
1 stop
MCO
11:50a
MDW
5:27p
5h 37m
1 stop
Depart: Wed Sep 9 2015 Return: Sat Sep 12 2015 Trip spans 4 days
Delta
Delta
MDW
11:20a
MCO
3:28p
4h 08m
1 stop
MCO
1:30p
MDW
7:05p
5h 35m
1 stop
Depart: Sat Sep 12 2015 Return: Tue Sep 15 2015 Trip spans 4 days
Delta
Delta
MDW
8:29a
MCO
12:35p
4h 06m
1 stop
MCO
5:30a
MDW
10:15a
4h 45m
1 stop
Depart: Tue Sep 15 2015 Return: Sat Sep 19 2015 Trip spans 5 days
Delta
Delta
MDW
1:59p
MCO
7:21p
5h 22m
1 stop
MCO
6:20a
MDW
11:44a
5h 24m
1 stop
Depart: Wed Sep 16 2015 Return: Sat Sep 19 2015 Trip spans 4 days
Delta
Delta
MDW
5:17a
MCO
9:53a
4h 36m
1 stop
MCO
6:20a
MDW
11:44a
5h 24m
1 stop
Depart: Sat Sep 19 2015 Return: Thu Sep 24 2015 Trip spans 6 days
Delta
Delta
MDW
11:11a
MCO
4:50p
5h 39m
1 stop
MCO
1:20a
MDW
6:18a
4h 58m
1 stop
Depart: Mon Sep 21 2015 Return: Mon Sep 28 2015 Trip spans 8 days
Delta
Delta
MDW
1:59p
MCO
7:21p
5h 22m
1 stop
MCO
11:30a
MDW
5:12p
5h 42m
1 stop
Depart: Tue Sep 22 2015 Return: Sat Sep 26 2015 Trip spans 5 days
Delta
Delta
MDW
3:00a
MCO
9:53a
6h 53m
1 stop
MCO
1:20a
MDW
6:12a
4h 52m
1 stop
Depart: Wed Sep 23 2015 Return: Sat Sep 26 2015 Trip spans 4 days
Delta
Delta
MDW
9:50a
MCO
3:28p
5h 38m
1 stop
MCO
1:20a
MDW
6:12a
4h 52m
1 stop
Depart: Thu Sep 24 2015 Return: Mon Sep 28 2015 Trip spans 5 days
Delta
Delta
MDW
2:00a
MCO
8:15a
6h 15m
1 stop
MCO
5:30a
MDW
11:45a
6h 15m
1 stop
Depart: Fri Sep 25 2015 Return: Sun Sep 27 2015 Trip spans 3 days
Delta
Delta
MDW
3:15p
MCO
7:21p
4h 06m
1 stop
MCO
4:20a
MDW
9:23a
5h 03m
1 stop
Depart: Sat Sep 26 2015 Return: Mon Sep 28 2015 Trip spans 3 days
Delta
Delta
MDW
1:59p
MCO
6:20p
4h 21m
1 stop
MCO
5:30a
MDW
10:15a
4h 45m
1 stop
Depart: Mon Sep 28 2015 Return: Mon Oct 5 2015 Trip spans 8 days
Delta
Delta
MDW
3:15p
MCO
7:21p
4h 06m
1 stop
MCO
4:30a
MDW
8:53a
4h 23m
1 stop
Depart: Tue Sep 29 2015 Return: Sat Oct 3 2015 Trip spans 5 days
Delta
Delta
MDW
3:15p
MCO
7:21p
4h 06m
1 stop
MCO
2:15a
MDW
6:51a
4h 36m
1 stop
Depart: Wed Sep 30 2015 Return: Tue Oct 6 2015 Trip spans 7 days
Delta
Delta
MDW
3:15p
MCO
7:21p
4h 06m
1 stop
MCO
4:30a
MDW
8:53a
4h 23m
1 stop
Depart: Fri Oct 2 2015 Return: Sun Oct 4 2015 Trip spans 3 days
Delta
Delta
MDW
3:15p
MCO
7:30p
4h 15m
1 stop
MCO
2:30a
MDW
9:15a
6h 45m
1 stop
Depart: Sat Oct 3 2015 Return: Mon Oct 5 2015 Trip spans 3 days
Delta
Delta
MDW
12:35p
MCO
5:32p
4h 57m
1 stop
MCO
7:10a
MDW
12:52p
5h 42m
1 stop
Depart: Sun Oct 4 2015 Return: Sun Oct 11 2015 Trip spans 8 days
Delta
Delta
MDW
3:15p
MCO
7:30p
4h 15m
1 stop
MCO
2:30a
MDW
9:15a
6h 45m
1 stop
Depart: Mon Oct 5 2015 Return: Tue Oct 13 2015 Trip spans 9 days
Delta
Delta
MDW
11:20a
MCO
3:27p
4h 07m
1 stop
MCO
4:30a
MDW
8:53a
4h 23m
1 stop
Depart: Tue Oct 6 2015 Return: Sat Oct 10 2015 Trip spans 5 days
Delta
Delta
MDW
3:15p
MCO
7:30p
4h 15m
1 stop
MCO
2:15a
MDW
6:51a
4h 36m
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
6366 6:05 am 9:35 am Sep 11 - Oct 29
6372 6:05 am 9:35 am Sep 8 - Sep 10
4519 7:10 am 10:40 am Sep 12 - Oct 31
3886 8:00 am 11:30 am Sep 12 - Oct 24
3017 8:15 am 11:45 am Aug 27 - Sep 10
985 8:15 am 11:45 am Sep 6 - Sep 6
3166 9:20 am 12:50 pm Sep 6 - Sep 6
4440 9:25 am 12:55 pm Sep 12 - Oct 31
894 10:25 am 1:55 pm Oct 3 - Oct 24
924 10:25 am 1:55 pm Sep 12 - Sep 26
6200 11:40 am 3:10 pm Sep 7 - Sep 7
669 11:40 am 3:10 pm Aug 30 - Sep 6
669 11:40 am 3:10 pm Sep 8 - Oct 30
4745 1:20 pm 5:00 pm Sep 12 - Sep 26
4745 1:25 pm 5:00 pm Oct 3 - Oct 24
1745 1:35 pm 5:15 pm Sep 7 - Sep 7
660 1:35 pm 5:15 pm Sep 8 - Sep 10
660 1:35 pm 5:15 pm Sep 11 - Sep 25
3079 1:40 pm 5:20 pm Sep 6 - Sep 6
660 1:40 pm 5:15 pm Sep 27 - Oct 30
1101 3:00 pm 6:35 pm Sep 6 - Sep 6
2887 3:00 pm 6:35 pm Oct 5 - Oct 30
2887 3:00 pm 6:35 pm Sep 28 - Oct 2
2887 3:00 pm 6:35 pm Sep 21 - Sep 25
2887 3:00 pm 6:35 pm Sep 8 - Sep 11
2887 3:00 pm 6:35 pm Sep 14 - Sep 18
6530 3:00 pm 6:35 pm Sep 7 - Sep 7
1487 3:05 pm 6:40 pm Sep 27 - Oct 25
3362 3:05 pm 6:40 pm Sep 13 - Sep 20
1755 3:15 pm 6:50 pm Sep 12 - Sep 19
1755 3:15 pm 6:50 pm Sep 26 - Sep 26
1620 3:25 pm 7:00 pm Oct 3 - Oct 24
2159 4:20 pm 7:55 pm Sep 27 - Oct 30
2159 4:20 pm 7:55 pm Sep 7 - Sep 18
2159 4:20 pm 7:55 pm Sep 20 - Sep 25
2159 4:20 pm 7:55 pm Sep 6 - Sep 6
4763 4:50 pm 8:25 pm Oct 3 - Oct 24
4763 4:50 pm 8:25 pm Sep 12 - Sep 26
2109 7:00 pm 10:30 pm Sep 13 - Oct 25
2209 7:00 pm 10:30 pm Aug 31 - Oct 30
Airports
Origin

Chicago
$214
Destination

Orlando
$214
Airlines