SEARCH ONE AND DONE. - Compare hundreds of travel sites at once.
Choose where to book.
Find deals from over 400 airlines worldwide.

Cheap Flights from Orlando to Chicago (MCO - 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.
Choose Sites to Compare vs. KAYAK

Best fares from MCO to MDW (Found by others)

Sun Mon Tue Wed Thu Fri Sat
  1 $478 2 $409 3 $409 4 $409 5 $393 6 $409
7 $324 8 $340 9 $311 10 $312 11 $340 12 $340 13 $371
14 $423 15 $337 16 $272 17 $301 18 $301 19 $322 20 $273
21 $339 22 $278 23 $265 24 $265 25 $237 26 $237 27 $259
28
$259
29 $291 30
$291
       
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 MCO 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 Aug 28 - Sep 8
230 9:05 am 10:50 am Sep 9 - Nov 1
145 3:36 pm 5:21 pm Aug 28 - Sep 8
145 3:36 pm 5:21 pm Sep 9 - Oct 31
143 8:40 pm 10:25 pm Sep 9 - Oct 30
143 8:50 pm 10:35 pm Sep 7 - Sep 8