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Cheap Flights from Orlando to Chicago (ORL - MDW)

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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)

Sun Mon Tue Wed Thu Fri Sat
        1 $284 2 $440 3 $284
4 $380 5 $433 6 $284 7 $211 8 $258 9 $307 10 $282
11 $271 12 $271 13 $258 14 $258 15 $242 16 $271 17 $269
18 $294 19 $271 20 $258 21 $258 22 $271 23 $294 24 $262
25 $271 26 $294 27 $258 28 $258 29 $258 30 $258 31
$258
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 direct on the airline or travel agent site of your choice!
Select an airline:  AirTran
Direct flights ORL to MDW on AirTran
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
305 7:15 am 9:00 am Apr 22 - Jun 6
214 9:30 am 11:15 am Apr 26 - Jun 7
342 12:25 pm 2:10 pm Apr 22 - Jun 6
320 1:40 pm 3:20 pm Apr 26 - Jun 7
2277 2:55 pm 4:35 pm May 26 - May 26
2802 2:55 pm 4:40 pm Apr 27 - May 23
2519 5:10 pm 6:55 pm May 27 - Jun 6
2519 5:10 pm 6:55 pm Apr 27 - May 23
2933 5:10 pm 6:55 pm May 26 - May 26
3154 5:40 pm 7:30 pm May 3 - May 17
3154 5:40 pm 7:30 pm May 31 - May 31
5307 6:20 pm 8:05 pm May 4 - May 9
5307 6:20 pm 8:05 pm May 2 - May 2
5307 6:20 pm 8:05 pm May 16 - Jun 6
5196 6:25 pm 8:15 pm May 31 - May 31
5196 6:25 pm 8:15 pm May 3 - May 17
5196 6:40 pm 8:25 pm May 24 - May 24