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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
1417 06:50 08:30 6 Sep - 27 Sep
5785 06:50 08:30 16 Aug - 23 Aug
1212 07:00 08:50 29 Jul - 8 Aug
4379 07:00 08:45 2 Sep - 29 Sep
4379 07:05 08:50 26 Aug - 1 Sep
2444 07:10 08:55 30 Aug - 30 Aug
5784 07:10 08:50 10 Aug - 25 Aug
2753 07:30 09:25 9 Aug - 9 Aug
2628 08:45 10:40 2 Aug - 9 Aug
2286 08:55 10:40 31 Aug - 31 Aug
5230 09:05 10:50 10 Aug - 1 Nov
1779 09:10 10:55 29 Jul - 8 Aug
5230 09:35 11:15 9 Aug - 9 Aug
5230 10:00 11:40 29 Jul - 8 Aug
1536 10:50 12:35 31 Aug - 31 Aug
4573 10:50 12:35 10 Aug - 24 Aug
4573 10:50 12:35 7 Sep - 28 Sep
689 10:50 12:35 11 Aug - 29 Sep
3125 11:15 13:00 29 Jul - 8 Aug
1583 11:30 13:15 6 Sep - 27 Sep
1583 11:30 13:15 16 Aug - 30 Aug
392 11:35 13:30 9 Aug - 9 Aug
925 12:35 14:15 6 Sep - 25 Oct
4172 12:45 14:40 2 Aug - 9 Aug
5147 12:45 14:25 10 Aug - 1 Sep
4735 13:00 14:40 2 Sep - 31 Oct
1016 14:00 15:50 16 Aug - 23 Aug
1016 14:00 15:50 6 Sep - 27 Sep
2407 14:00 15:50 29 Jul - 8 Aug
2990 14:05 15:55 30 Aug - 30 Aug
5145 14:35 16:20 9 Aug - 9 Aug
5145 15:00 16:45 29 Jul - 8 Aug
5145 15:36 17:21 10 Aug - 31 Oct
1844 15:50 17:50 9 Aug - 9 Aug
1776 16:00 17:45 6 Sep - 27 Sep
1776 16:00 17:45 16 Aug - 23 Aug
1579 17:50 19:45 29 Jul - 8 Aug
3224 18:00 19:45 30 Aug - 30 Aug
3224 18:00 19:45 16 Aug - 23 Aug
3224 18:00 19:45 6 Sep - 27 Sep
2748 18:10 19:55 9 Aug - 9 Aug
3884 18:40 20:35 31 Jul - 8 Aug
3240 19:10 21:05 2 Aug - 9 Aug
636 19:25 21:15 1 Sep - 1 Sep
943 19:25 21:15 10 Aug - 29 Aug
943 19:25 21:15 2 Sep - 14 Sep
4337 19:30 21:20 31 Aug - 31 Aug
5143 20:50 22:45 29 Jul - 9 Aug
5143 20:50 22:35 1 Sep - 8 Sep
5143 20:50 22:35 10 Aug - 30 Aug
419 21:45 23:25 29 Jul - 8 Aug
2887 21:55 23:35 2 Aug - 9 Aug