Cheap Flights from Chicago to Cancun (MDW - CUN)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none

Best fares from MDW to CUN

Sun Mon Tue Wed Thu Fri Sat
  1 $538 2 $538 3 $452 4 $518 5 $518 6 $437
7 $432 8 $432 9 $432 10 $432 11 $491 12 $466 13 $432
14 $558 15 $514 16 $581 17 $564 18 $688 19 $741 20 $670
21 $603 22 $561 23 $541 24 $518 25 $598 26 $634 27 $539
28 $531 29 $521 30 $499 31 $478      

Best fares found by others...

KAYAK searches hundreds of sites to find the best rate for your next flight from Chicago to Cancun. Get the best flight deal for your Cancun trip!
Here's how it works. Search KAYAK for a flight ticket from Chicago to Cancun. 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:  Southwest
Direct flights MDW to CUN on Southwest
Flight # Depart MDW Arrive CUN Sun Mon Tue Wed Thu Fri Sat Valid Between
216 7:00 am 11:00 am Nov 20 - Jan 4
218 9:05 am 1:00 pm Nov 20 - Jan 2
228 9:10 am 1:05 pm Nov 22 - Dec 27