SEARCH ONE AND DONE. - Compare hundreds of travel sites at once.
Choose where to book.
Find deals from over 400 airlines worldwide.
You could save up to 30% on the same flight.

Cheap Flights from Orlando to Chicago (ORL - MDW)

DepartReturn
1 adult
Note: some airlines charge for infants in laps.
The price shown for each flight will be the average for all passengers, including any infants.
Choose Sites to Compare vs. KAYAK

Best fares from ORL to MDW (Found by others)

Mon Tue Wed Thu Fri Sat Sun
          1
₹ 2
2
₹ 2
3
₹ 2
4
₹ 2
5
₹ 2
6
₹ 2
7
₹ 2
8
₹ 2
9
₹ 2
10
₹ 2
11
₹ 2
12
₹ 2
13
₹ 2
14
₹ 2
15
₹ 2
16
₹ 2
17
₹ 2
18
₹ 2
19
₹ 2
20
₹ 2
21
₹ 2
22
₹ 2
23
₹ 2
24
₹ 2
25
₹ 2
26
₹ 2
27
₹ 2
28
₹ 2
29
₹ 2
30
₹ 2
KAYAK searches hundreds of sites to find the best rate for your next flight from Orlando to Chicago. Get the best flight deal for your Chicago trip!
Here's how it works. Search KAYAK for a flight ticket from Orlando to Chicago. Sort, filter and compare results on one web page. Then book your plane ticket directly on the airline or travel agent site of your choice!
Select an airline:  Southwest
Direct flights ORL - MDW on Southwest
Flight No. Departure MCO Arrival MDW Sun Mon Tue Wed Thu Fri Sat Valid between
1410 06:45 08:45 25 Nov - 1 Dec
4309 06:45 08:25 18 Oct - 1 Nov
4379 07:00 08:45 31 Oct - 31 Oct
4379 07:05 08:50 19 Oct - 30 Oct
4134 07:15 09:10 11 Nov - 24 Nov
4134 07:20 09:10 27 Nov - 29 Nov
6034 07:20 09:10 2 Nov - 10 Nov
1463 07:25 09:20 15 Nov - 22 Nov
6134 07:30 09:20 8 Nov - 8 Nov
3984 07:40 09:40 25 Nov - 1 Dec
3616 09:05 10:55 25 Nov - 1 Dec
5230 09:05 10:50 18 Oct - 1 Nov
1780 09:20 11:10 27 Nov - 27 Nov
1986 09:20 11:10 2 Nov - 24 Nov
1129 10:30 12:20 28 Nov - 28 Nov
689 10:50 12:35 20 Oct - 30 Oct
923 10:55 12:40 31 Oct - 31 Oct
219 11:30 13:15 1 Nov - 1 Nov
4294 11:45 13:40 8 Nov - 22 Nov
357 12:30 14:20 25 Nov - 1 Dec
1040 12:35 14:15 1 Nov - 1 Nov
4139 12:35 14:25 27 Nov - 5 Dec
4139 12:35 14:25 11 Nov - 24 Nov
6039 12:35 14:25 2 Nov - 10 Nov
4735 12:40 14:20 26 Oct - 30 Oct
4735 13:00 14:40 31 Oct - 31 Oct
2265 13:45 15:35 25 Nov - 1 Dec
1098 14:00 15:50 1 Nov - 1 Nov
1512 14:05 15:55 27 Nov - 29 Nov
4508 14:05 15:55 11 Nov - 24 Nov
6036 14:05 15:55 2 Nov - 10 Nov
1502 14:15 16:05 15 Nov - 22 Nov
6136 14:15 16:05 8 Nov - 8 Nov
2614 14:55 16:45 28 Nov - 28 Nov
128 15:10 17:00 27 Nov - 27 Nov
2593 15:10 17:00 2 Nov - 24 Nov
4250 15:35 17:30 8 Nov - 22 Nov
5145 15:36 17:21 19 Oct - 31 Oct
4314 16:05 18:00 18 Oct - 1 Nov
663 16:25 18:15 27 Nov - 27 Nov
663 16:25 18:15 28 Nov - 29 Nov
671 16:25 18:15 2 Nov - 24 Nov
3532 16:35 18:25 25 Nov - 1 Dec
4460 16:45 18:35 8 Nov - 22 Nov
3224 18:00 19:55 18 Oct - 1 Nov
1680 18:15 20:05 8 Nov - 22 Nov
1372 18:50 20:40 27 Nov - 27 Nov
4041 19:20 21:10 28 Nov - 29 Nov
4318 19:20 21:10 11 Nov - 24 Nov
4604 19:20 21:10 8 Nov - 22 Nov
6041 19:20 21:10 2 Nov - 10 Nov
753 19:25 21:15 19 Oct - 30 Oct
302 19:30 21:20 25 Nov - 1 Dec
399 19:35 21:25 31 Oct - 31 Oct
1341 20:05 21:55 15 Nov - 22 Nov
6141 20:05 21:55 8 Nov - 8 Nov
5143 20:40 22:25 18 Oct - 30 Oct
5147 20:50 22:35 1 Nov - 1 Nov
1186 21:15 23:05 28 Nov - 5 Dec
1186 21:15 23:05 2 Nov - 24 Nov
3989 22:35 00:25 25 Nov - 1 Dec