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 Cancun to Chicago (CUN - 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 CUN to MDW (Found by others)

Sun Mon Tue Wed Thu Fri Sat
          1 $538 2 $502
3
$502
4 $557 5 $615 6
$615
7
$615
8
$615
9
$615
10 $735 11
$735
12
$735
13 $553 14 $706 15
$706
16
$706
17
$706
18 $873 19
$873
20 $757 21 $650 22
$650
23
$650
24 $888 25
$888
26
$888
27
$888
28
$888
29
$888
30
$888
31
$888
           
KAYAK searches hundreds of sites to find the best rate for your next flight from Cancun to Chicago. Get the best flight deal for your Chicago trip!
Here's how it works. Search KAYAK for a flight ticket from Cancun 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 CUN to MDW on AirTran
Flight # Depart CUN Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
219 1:25 pm 4:58 pm Jul 31 - Aug 9
219 1:35 pm 5:10 pm Aug 10 - Oct 24
226 1:55 pm 5:30 pm Aug 16 - Sep 6