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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 Mon Tue Wed Thu Fri Sat Sun Valid between
1410 06:45 08:45 25 Nov - 1 Dec
4537 06:45 08:45 30 Nov - 30 Nov
4134 07:15 09:10 2 Dec - 23 Dec
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
1463 07:25 09:20 6 Dec - 13 Dec
6134 07:30 09:20 8 Nov - 8 Nov
2712 07:40 09:40 30 Nov - 30 Nov
3984 07:40 09:40 25 Nov - 1 Dec
3616 09:05 10:55 25 Nov - 1 Dec
1780 09:20 11:10 27 Nov - 27 Nov
1986 09:20 11:10 2 Nov - 24 Nov
1986 09:20 11:10 29 Nov - 5 Dec
1986 09:20 11:10 7 Dec - 19 Dec
4242 09:30 11:20 30 Nov - 30 Nov
1129 10:30 12:20 28 Nov - 28 Nov
4294 11:45 13:40 8 Nov - 22 Nov
4294 11:45 13:40 6 Dec - 13 Dec
357 12:30 14:20 25 Nov - 1 Dec
3815 12:35 14:25 30 Nov - 30 Nov
4139 12:35 14:25 11 Nov - 24 Nov
4139 12:35 14:25 7 Dec - 23 Dec
4139 12:35 14:25 27 Nov - 5 Dec
6039 12:35 14:25 2 Nov - 10 Nov
2265 13:45 15:35 25 Nov - 1 Dec
4067 13:45 15:35 30 Nov - 30 Nov
1512 14:05 15:55 27 Nov - 29 Nov
4508 14:05 15:55 2 Dec - 23 Dec
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
1502 14:15 16:05 6 Dec - 13 Dec
6136 14:15 16:05 8 Nov - 8 Nov
2614 14:55 16:45 28 Nov - 28 Nov
128 15:10 17:00 29 Nov - 29 Nov
128 15:10 17:00 27 Nov - 27 Nov
2593 15:10 17:00 2 Nov - 24 Nov
2593 15:10 17:00 2 Dec - 23 Dec
4250 15:35 17:30 8 Nov - 22 Nov
4250 15:35 17:30 6 Dec - 13 Dec
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
671 16:25 18:15 2 Dec - 19 Dec
346 16:30 18:20 30 Nov - 30 Nov
3532 16:35 18:25 25 Nov - 1 Dec
4460 16:45 18:35 8 Nov - 22 Nov
4460 16:45 18:35 6 Dec - 13 Dec
1680 18:15 20:05 8 Nov - 22 Nov
1680 18:15 20:05 6 Dec - 13 Dec
1372 18:50 20:40 27 Nov - 27 Nov
1230 19:15 21:05 30 Nov - 30 Nov
4041 19:20 21:10 28 Nov - 29 Nov
4318 19:20 21:10 11 Nov - 24 Nov
4318 19:20 21:10 2 Dec - 23 Dec
4604 19:20 21:10 8 Nov - 22 Nov
4604 19:20 21:10 6 Dec - 13 Dec
6041 19:20 21:10 2 Nov - 10 Nov
302 19:30 21:20 25 Nov - 1 Dec
1341 20:05 21:55 15 Nov - 22 Nov
1341 20:05 21:55 6 Dec - 13 Dec
6141 20:05 21:55 8 Nov - 8 Nov
1186 21:15 23:05 2 Nov - 24 Nov
1186 21:15 23:05 28 Nov - 5 Dec
1186 21:15 23:05 7 Dec - 19 Dec
1189 22:35 00:25 30 Nov - 30 Nov
3989 22:35 00:25 25 Nov - 1 Dec