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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.
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Best fares from ORL to MDW (Found by others)

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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
4309 06:45 08:25 4 Oct - 1 Nov
4379 07:00 08:45 31 Oct - 31 Oct
4379 07:05 08:50 30 Sep - 30 Oct
6034 07:20 09:10 2 Nov - 10 Nov
5230 09:05 10:50 27 Sep - 1 Nov
1986 09:20 11:10 2 Nov - 24 Nov
278 10:50 12:35 5 Oct - 26 Oct
689 10:50 12:35 30 Sep - 30 Oct
923 10:55 12:40 31 Oct - 31 Oct
1353 11:30 13:15 25 Oct - 25 Oct
1353 11:30 13:15 4 Oct - 18 Oct
219 11:30 13:15 1 Nov - 1 Nov
1040 12:35 14:15 1 Nov - 1 Nov
6039 12:35 14:25 2 Nov - 10 Nov
925 12:35 14:15 27 Sep - 25 Oct
4735 12:40 14:20 26 Oct - 30 Oct
4735 13:00 14:40 31 Oct - 31 Oct
4735 13:00 14:40 28 Sep - 24 Oct
1016 14:00 15:50 4 Oct - 25 Oct
1098 14:00 15:50 1 Nov - 1 Nov
6036 14:05 15:55 2 Nov - 10 Nov
2593 15:10 17:00 2 Nov - 24 Nov
5145 15:36 17:21 28 Sep - 31 Oct
4314 16:05 18:00 4 Oct - 1 Nov
671 16:25 18:15 2 Nov - 24 Nov
3224 18:00 19:55 4 Oct - 1 Nov
6041 19:20 21:10 2 Nov - 10 Nov
753 19:25 21:15 30 Sep - 30 Oct
399 19:35 21:25 31 Oct - 31 Oct
5143 20:40 22:25 27 Sep - 30 Oct
5147 20:50 22:35 1 Nov - 1 Nov
1186 21:15 23:05 2 Nov - 24 Nov