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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 $260 2 $260 3 $260 4 $296
5 $375 6 $324 7 $255 8 $255 9 $260 10 $326 11 $260
12 $356 13 $420 14 $324 15 $263 16 $268 17 $338 18 $354
19 $364 20 $348 21 $304 22 $255 23 $260 24 $268 25 $342
26 $373 27 $299 28 $273 29 $272 30 $268 31 $282  
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!
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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
230 9:05 am 10:50 am Sep 16 - Sep 29
230 9:05 am 10:50 am Sep 30 - Nov 1
145 3:36 pm 5:21 pm Sep 30 - Oct 31
145 3:36 pm 5:21 pm Sep 16 - Sep 29
143 8:40 pm 10:25 pm Sep 30 - Oct 30
143 8:40 pm 10:25 pm Sep 16 - Sep 29