Browse Origins:
Browse Destinations:

Find Flight Deals from Chicago Midway to Orlando (MDW - MCO)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Orlando

(Round-trip)
Depart: Tue Jun 16 2015 Return: Tue Jun 23 2015 Trip spans 8 days
Delta
Delta
MDW
3:28p
MCO
7:38p
4h 10m
1 stop
MCO
1:30p
MDW
7:17p
5h 47m
1 stop
Depart: Tue Jun 23 2015 Return: Wed Jun 24 2015 Trip spans 2 days
Delta
Delta
MDW
8:29a
MCO
2:45p
6h 16m
1 stop
MCO
11:30a
MDW
7:17p
7h 47m
1 stop
Depart: Wed Jun 24 2015 Return: Tue Jun 30 2015 Trip spans 7 days
Delta
Delta
MDW
3:28p
MCO
7:38p
4h 10m
1 stop
MCO
4:20a
MDW
9:27a
5h 07m
1 stop
Depart: Tue Jun 30 2015 Return: Wed Jul 1 2015 Trip spans 2 days
Delta
Delta
MDW
8:29a
MCO
1:32p
5h 03m
1 stop
MCO
4:20a
MDW
10:18a
5h 58m
1 stop
Depart: Wed Jul 1 2015 Return: Wed Jul 8 2015 Trip spans 8 days
Delta
Delta
MDW
8:19a
MCO
1:35p
5h 16m
1 stop
MCO
6:20a
MDW
12:07p
5h 47m
1 stop
Depart: Sat Jul 4 2015 Return: Wed Jul 8 2015 Trip spans 5 days
Delta
Delta
MDW
11:42a
MCO
5:23p
5h 41m
1 stop
MCO
2:30p
MDW
7:14p
4h 44m
1 stop
Depart: Wed Jul 8 2015 Return: Tue Jul 14 2015 Trip spans 7 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
10:00a
MDW
2:53p
4h 53m
1 stop
Depart: Tue Jul 14 2015 Return: Tue Jul 21 2015 Trip spans 8 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
2:30p
MDW
7:14p
4h 44m
1 stop
Depart: Wed Jul 15 2015 Return: Tue Jul 21 2015 Trip spans 7 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
5:30a
MDW
10:18a
4h 48m
1 stop
Depart: Tue Jul 21 2015 Return: Tue Jul 28 2015 Trip spans 8 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
11:30a
MDW
5:20p
5h 50m
1 stop
Depart: Wed Jul 22 2015 Return: Tue Jul 28 2015 Trip spans 7 days
Delta
Delta
MDW
3:05a
MCO
8:21a
5h 16m
1 stop
MCO
3:00a
MDW
9:23a
6h 23m
1 stop
Depart: Tue Jul 28 2015 Return: Tue Aug 4 2015 Trip spans 8 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
9:30a
MDW
2:37p
5h 07m
1 stop
Depart: Wed Jul 29 2015 Return: Tue Aug 4 2015 Trip spans 7 days
Delta
Delta
MDW
8:19a
MCO
1:35p
5h 16m
1 stop
MCO
1:30p
MDW
7:14p
5h 44m
1 stop
Depart: Tue Aug 4 2015 Return: Wed Aug 5 2015 Trip spans 2 days
Delta
Delta
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
MCO
2:30p
MDW
7:14p
4h 44m
1 stop
Depart: Wed Aug 5 2015 Return: Tue Aug 11 2015 Trip spans 7 days
Delta
Delta
MDW
3:05a
MCO
7:27a
4h 22m
1 stop
MCO
5:30a
MDW
10:18a
4h 48m
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
5:30a
MDW
10:05a
4h 35m
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: Tue Aug 18 2015 Return: Sat Aug 22 2015 Trip spans 5 days
Delta
Delta
MDW
5:55a
MCO
10:36a
4h 41m
1 stop
MCO
1:30p
MDW
7:10p
5h 40m
1 stop
Depart: Wed Aug 19 2015 Return: Sat Aug 22 2015 Trip spans 4 days
Delta
Delta
MDW
9:40a
MCO
2:35p
4h 55m
1 stop
MCO
1:30p
MDW
7:10p
5h 40m
1 stop
Depart: Mon Aug 31 2015 Return: Mon Sep 7 2015 Trip spans 8 days
Sun Country Air
Sun Country Air
MDW
4:00a
MCO
7:08a
27h 08m
1 stop
MCO
9:00a
MDW
5:45p
8h 45m
1 stop
Select an airline:  Southwest
Direct flights MDW to MCO on Southwest
Flight # Depart MDW Arrive MCO Sun Mon Tue Wed Thu Fri Sat Valid Between
2644 5:35 am 9:05 am Jun 13 - Jun 27
1891 6:00 am 9:30 am Jul 3 - Jul 3
1891 6:00 am 9:35 am Jun 7 - Jul 2
845 6:00 am 9:45 am May 31 - Jun 5
1370 6:50 am 10:25 am Jun 13 - Jun 27
1839 6:50 am 10:30 am Jun 6 - Jun 6
3028 7:00 am 10:35 am Jun 7 - Aug 2
3028 7:00 am 10:35 am Jun 8 - Jul 2
3028 7:05 am 10:40 am Jul 3 - Jul 3
4639 7:05 am 10:35 am May 21 - Jun 5
2727 7:20 am 10:50 am May 30 - Jun 6
2312 7:35 am 11:05 am Jun 13 - Jun 27
2474 8:15 am 11:50 am Jun 6 - Jun 6
4068 9:00 am 12:30 pm Jun 7 - Jun 7
4068 9:00 am 12:30 pm Jun 21 - Aug 2
4068 9:00 am 12:30 pm Jun 14 - Jun 14
1617 9:10 am 12:40 pm Jul 3 - Jul 3
1617 9:15 am 12:45 pm Jun 8 - Jul 2
2058 9:50 am 1:20 pm Jun 13 - Jun 27
3305 10:20 am 1:55 pm Jun 6 - Jun 6
2671 10:35 am 2:10 pm May 31 - Jun 5
2258 10:40 am 2:10 pm Jun 8 - Jul 31
4116 10:40 am 2:10 pm Jun 7 - Aug 2
4378 11:15 am 2:50 pm Jun 13 - Jun 27
1114 12:10 pm 3:45 pm Jun 6 - Jun 6
1636 12:10 pm 3:45 pm Jun 15 - Jul 2
1636 12:10 pm 3:45 pm Jun 8 - Jun 12
2019 12:10 pm 3:45 pm Jul 3 - Jul 3
612 12:10 pm 3:45 pm Jun 7 - Aug 2
3753 1:15 pm 4:55 pm Jun 6 - Jun 6
1979 1:20 pm 5:00 pm May 31 - Jun 5
1807 1:30 pm 5:15 pm Jun 13 - Jun 27
4930 1:35 pm 5:25 pm Jun 7 - Aug 7
1515 3:40 pm 7:20 pm Jul 3 - Aug 7
1515 3:40 pm 7:20 pm Jun 28 - Jul 2
1515 3:40 pm 7:20 pm Jun 7 - Jun 26
2040 3:50 pm 7:30 pm Jun 13 - Jun 27
1603 3:55 pm 7:30 pm May 30 - Jun 6
2065 4:30 pm 8:10 pm Jun 13 - Jun 27
4589 4:55 pm 8:30 pm May 31 - Jun 5
958 5:00 pm 8:35 pm May 30 - Jun 6
1318 5:15 pm 9:00 pm Jun 13 - Jun 27
313 5:25 pm 9:00 pm Jun 7 - Jul 2
4705 5:45 pm 9:20 pm Jul 3 - Jul 3
540 5:50 pm 9:30 pm Jun 1 - Jun 5
4249 6:00 pm 9:45 pm Jun 13 - Jun 27
1716 6:25 pm 10:00 pm May 30 - Jun 6
3041 8:35 pm 12:10 am Jun 7 - Jul 2
4612 9:15 pm 12:50 am Jun 13 - Jun 27
594 9:20 pm 12:50 am May 31 - Jun 5
Airports
Origin

Chicago
$286
Destination

Orlando
$286