Find Deals on Flights from Chicago Midway to Cancun (MDW - CUN)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Cancun

(Round-trip)
Depart: Mon May 23 2016 Return: Fri May 27 2016 Trip spans 5 days
Depart: Mon May 9 2016 Return: Tue May 17 2016 Trip spans 9 days
Depart: Sun Aug 7 2016 Return: Sun Aug 14 2016 Trip spans 8 days
Depart: Thu Oct 20 2016 Return: Sat Oct 29 2016 Trip spans 10 days
Depart: Tue May 10 2016 Return: Tue May 17 2016 Trip spans 8 days
Depart: Fri Jun 24 2016 Return: Wed Jun 29 2016 Trip spans 6 days
Depart: Wed May 11 2016 Return: Tue May 17 2016 Trip spans 7 days
Depart: Mon May 30 2016 Return: Thu Jun 2 2016 Trip spans 4 days
Depart: Sat Jul 23 2016 Return: Tue Jul 26 2016 Trip spans 4 days
Depart: Thu Sep 29 2016 Return: Thu Oct 6 2016 Trip spans 8 days
Depart: Sun May 8 2016 Return: Wed May 11 2016 Trip spans 4 days
Depart: Thu Nov 24 2016 Return: Sat Nov 26 2016 Trip spans 3 days
Depart: Sat May 14 2016 Return: Tue May 17 2016 Trip spans 4 days
Depart: Wed May 18 2016 Return: Thu May 26 2016 Trip spans 9 days
Depart: Sun Aug 21 2016 Return: Fri Aug 26 2016 Trip spans 6 days
Depart: Tue May 31 2016 Return: Wed Jun 22 2016 Trip spans 23 days
Depart: Mon Aug 22 2016 Return: Fri Aug 26 2016 Trip spans 5 days
Depart: Wed Jun 1 2016 Return: Wed Jun 8 2016 Trip spans 8 days
Depart: Thu Sep 22 2016 Return: Tue Sep 27 2016 Trip spans 6 days
Depart: Wed Jun 8 2016 Return: Wed Jun 15 2016 Trip spans 8 days
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
4949 5:30 am 9:00 am Apr 30 - Jun 4
216 7:10 am 10:45 am Apr 28 - Jun 3
216 7:15 am 10:40 am Jun 11 - Aug 6
216 7:15 am 10:40 am Jun 5 - Aug 5
218 9:15 am 12:40 pm Jun 5 - Aug 5
218 9:35 am 1:10 pm Apr 28 - Jun 3
228 9:55 am 1:30 pm Apr 30 - Jun 4
228 11:00 am 2:25 pm Jun 11 - Aug 6
230 12:35 pm 4:10 pm Apr 30 - Jun 4
230 1:50 pm 5:15 pm Jun 11 - Aug 6
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we don't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find on occasion that certain prices are no longer available.

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Airports
Origin

Chicago
$272
Destination

Cancun
$272