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: Thu May 7 2015 Return: Sun May 10 2015 Trip spans 4 days
Delta
Delta
MDW
8:50a
MCO
2:42p
5h 52m
1 stop
MCO
3:30a
MDW
10:51a
7h 21m
1 stop
Depart: Sat May 9 2015 Return: Sun May 10 2015 Trip spans 2 days
Delta
Delta
MDW
8:35a
MCO
3:26p
6h 51m
1 stop
MCO
2:30p
MDW
7:10p
4h 40m
1 stop
Depart: Sun May 10 2015 Return: Mon May 11 2015 Trip spans 2 days
Delta
Delta
MDW
3:00a
MCO
7:26a
4h 26m
1 stop
MCO
9:20a
MDW
2:24p
5h 04m
1 stop
Depart: Mon May 11 2015 Return: Tue May 12 2015 Trip spans 2 days
Delta
Delta
MDW
10:26a
MCO
2:44p
4h 18m
1 stop
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Tue May 12 2015 Return: Thu May 14 2015 Trip spans 3 days
Delta
Delta
MDW
2:00p
MCO
7:25p
5h 25m
1 stop
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Wed May 13 2015 Return: Sat May 16 2015 Trip spans 4 days
Delta
Delta
MDW
10:26a
MCO
2:44p
4h 18m
1 stop
MCO
2:30p
MDW
7:08p
4h 38m
1 stop
Depart: Thu May 14 2015 Return: Sat May 16 2015 Trip spans 3 days
Delta
Delta
MDW
3:00a
MCO
8:18a
5h 18m
1 stop
MCO
2:30p
MDW
7:08p
4h 38m
1 stop
Depart: Fri May 15 2015 Return: Mon May 18 2015 Trip spans 4 days
Delta
Delta
MDW
3:00a
MCO
8:18a
5h 18m
1 stop
MCO
11:14a
MDW
4:59p
5h 45m
1 stop
Depart: Sat May 16 2015 Return: Mon May 18 2015 Trip spans 3 days
Delta
Delta
MDW
1:59p
MCO
6:54p
4h 55m
1 stop
MCO
5:20a
MDW
10:51a
5h 31m
1 stop
Depart: Mon May 18 2015 Return: Tue May 19 2015 Trip spans 2 days
Delta
Delta
MDW
12:00p
MCO
4:31p
4h 31m
1 stop
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Tue May 19 2015 Return: Thu May 21 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
MCO
7:26a
5h 26m
1 stop
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Wed May 20 2015 Return: Fri May 22 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
MCO
7:26a
5h 26m
1 stop
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Thu May 21 2015 Return: Sat May 23 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
MCO
7:26a
5h 26m
1 stop
MCO
2:30p
MDW
7:08p
4h 38m
1 stop
Depart: Sat May 23 2015 Return: Tue May 26 2015 Trip spans 4 days
Delta
Delta
MDW
1:59p
MCO
6:15p
4h 16m
1 stop
MCO
12:20p
MDW
4:59p
4h 39m
1 stop
Depart: Sun May 24 2015 Return: Tue May 26 2015 Trip spans 3 days
Delta
Delta
MDW
10:26a
MCO
4:28p
6h 02m
1 stop
MCO
9:20a
MDW
2:24p
5h 04m
1 stop
Depart: Mon May 25 2015 Return: Tue May 26 2015 Trip spans 2 days
Delta
Delta
MDW
2:00a
MCO
8:18a
6h 18m
1 stop
MCO
1:20a
MDW
6:23a
5h 03m
1 stop
Depart: Tue May 26 2015 Return: Wed May 27 2015 Trip spans 2 days
Delta
Delta
MDW
3:00a
MCO
9:22a
6h 22m
1 stop
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Wed May 27 2015 Return: Sun May 31 2015 Trip spans 5 days
Delta
Delta
MDW
6:00a
MCO
12:25p
6h 25m
1 stop
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
Depart: Thu May 28 2015 Return: Sun May 31 2015 Trip spans 4 days
Delta
Delta
MDW
5:25a
MCO
9:47a
4h 22m
1 stop
MCO
2:30p
MDW
7:10p
4h 40m
1 stop
Depart: Thu Apr 30 2015 Return: Tue May 5 2015 Trip spans 6 days
Sun Country Air
Sun Country Air
MDW
6:30a
MCO
2:58p
56h 28m
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
2879 6:00 am 9:45 am May 25 - May 25
845 6:00 am 9:45 am Apr 8 - May 22
845 6:00 am 9:45 am May 26 - Jun 5
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 11 - May 16
4639 7:05 am 10:35 am Apr 8 - Jun 5
1768 7:20 am 10:50 am May 23 - May 23
2727 7:20 am 10:50 am Apr 11 - May 16
2474 8:20 am 11:55 am May 2 - May 16
2738 8:30 am 12:05 pm May 23 - May 23
3305 10:20 am 1:55 pm Apr 11 - May 30
2671 10:35 am 2:10 pm May 26 - Jun 5
2671 10:35 am 2:10 pm Apr 8 - 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 Apr 11 - May 16
34 12:20 pm 3:55 pm May 23 - May 23
3753 1:15 pm 4:55 pm Apr 11 - May 30
1979 1:20 pm 5:00 pm Apr 8 - May 22
1979 1:20 pm 5:00 pm May 26 - Jun 5
866 1:20 pm 5:00 pm May 24 - May 24
866 1:20 pm 5:00 pm May 25 - May 25
1603 3:55 pm 7:30 pm Apr 11 - May 16
1634 3:55 pm 7:30 pm May 23 - May 23
4589 4:55 pm 8:30 pm Apr 12 - 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 11 - May 16
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 10 - May 17
3702 5:50 pm 9:30 pm Apr 12 - Apr 26
3702 5:50 pm 9:30 pm May 3 - May 3
540 5:50 pm 9:30 pm Apr 8 - May 22
540 5:50 pm 9:30 pm May 26 - Jun 5
1716 6:25 pm 10:00 pm Apr 11 - May 2
1716 6:25 pm 10:00 pm May 9 - May 16
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 8 - May 22
594 9:25 pm 12:55 am May 24 - May 24
Airports
Origin

Chicago
$284
Destination

Orlando
$284