Find Cheap 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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Cancun

(Round-trip)
Depart: Wed Aug 9 2017 Return: Wed Oct 4 2017 Trip spans 57 days
Delta
Delta
MDW
12:00a
CUN
9:44a
9h 44m
1 stop
CUN
12:00a
MDW
8:46a
8h 46m
1 stop
Depart: Tue Aug 8 2017 Return: Wed Oct 4 2017 Trip spans 58 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
CUN
6:00a
6h 00m
1 stop
CUN
12:00a
MDW
1:05p
13h 05m
1 stop
Depart: Thu Aug 10 2017 Return: Thu Aug 17 2017 Trip spans 8 days
Volaris
Volaris
MDW
12:00a
CUN
2:46p
14h 46m
1 stop
CUN
12:00a
MDW
12:05p
12h 05m
1 stop
Depart: Thu Aug 10 2017 Return: Tue Oct 3 2017 Trip spans 55 days
Hahn Air Systems
Hahn Air Systems
MDW
12:00a
CUN
12:31a
24h 31m
1 stop
CUN
12:00a
MDW
12:13p
12h 13m
1 stop
Depart: Sat Jul 22 2017 Return: Mon Jul 24 2017 Trip spans 3 days
Delta
Delta
MDW
12:00a
CUN
6:37a
6h 37m
1 stop
CUN
12:00a
MDW
10:38a
10h 38m
1 stop
Depart: Fri Aug 11 2017 Return: Wed Oct 4 2017 Trip spans 55 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
CUN
1:12p
13h 12m
1 stop
CUN
12:00a
MDW
1:05p
13h 05m
1 stop
Depart: Wed Jul 26 2017 Return: Tue Aug 1 2017 Trip spans 7 days
Delta
Delta
MDW
12:00a
CUN
6:37a
6h 37m
1 stop
CUN
12:00a
MDW
8:49a
8h 49m
1 stop
Depart: Sat Jul 29 2017 Return: Tue Aug 1 2017 Trip spans 4 days
Delta
Delta
MDW
12:00a
CUN
6:37a
6h 37m
1 stop
CUN
12:00a
MDW
8:49a
8h 49m
1 stop
Depart: Sat Jul 22 2017 Return: Tue Jul 25 2017 Trip spans 4 days
Delta
Delta
MDW
12:00a
CUN
6:37a
6h 37m
1 stop
CUN
12:00a
MDW
12:00p
12h 00m
1 stop
Depart: Wed Jul 26 2017 Return: Wed Aug 2 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
CUN
6:37a
6h 37m
1 stop
CUN
12:00a
MDW
6:15a
6h 15m
1 stop
Depart: Thu Aug 3 2017 Return: Sat Aug 12 2017 Trip spans 10 days
Volaris
Volaris
MDW
12:00a
CUN
2:46p
14h 46m
1 stop
CUN
12:00a
MDW
12:05p
12h 05m
1 stop
Depart: Mon Jul 31 2017 Return: Wed Aug 9 2017 Trip spans 10 days
Delta
Delta
MDW
12:00a
CUN
5:50a
5h 50m
1 stop
CUN
12:00a
MDW
8:26a
8h 26m
1 stop
Depart: Mon Jul 31 2017 Return: Fri Aug 4 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
CUN
5:50a
5h 50m
1 stop
CUN
12:00a
MDW
1:05p
13h 05m
1 stop
Depart: Fri Jul 28 2017 Return: Sat Aug 26 2017 Trip spans 30 days
Volaris
Volaris
MDW
12:00a
CUN
2:46p
14h 46m
1 stop
CUN
12:00a
MDW
12:05p
12h 05m
1 stop
Depart: Thu Aug 10 2017 Return: Wed Oct 4 2017 Trip spans 56 days
Hahn Air Systems
Hahn Air Systems
MDW
12:00a
CUN
1:28a
25h 28m
1 stop
CUN
12:00a
MDW
1:05p
13h 05m
1 stop
Depart: Sat Jul 29 2017 Return: Fri Aug 4 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
CUN
1:51a
25h 51m
1 stop
CUN
12:00a
MDW
1:05p
13h 05m
1 stop
Depart: Mon Aug 7 2017 Return: Tue Oct 3 2017 Trip spans 58 days
Delta
Delta
MDW
12:00a
CUN
2:13p
14h 13m
1 stop
CUN
12:00a
MDW
2:03p
14h 03m
1 stop
Depart: Thu Aug 10 2017 Return: Sun Aug 20 2017 Trip spans 11 days
Volaris
Volaris
MDW
12:00a
CUN
2:46p
14h 46m
1 stop
CUN
12:00a
MDW
1:05p
13h 05m
1 stop
Depart: Tue Aug 8 2017 Return: Tue Oct 3 2017 Trip spans 57 days
Delta
Delta
MDW
12:00a
CUN
5:13a
5h 13m
1 stop
CUN
12:00a
MDW
2:03p
14h 03m
1 stop
Depart: Mon Aug 7 2017 Return: Sat Aug 12 2017 Trip spans 6 days
Volaris
Volaris
MDW
12:00a
CUN
2:46p
14h 46m
1 stop
CUN
12:00a
MDW
12:05p
12h 05m
1 stop
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 6:50 am 10:20 am Aug 19 - Nov 4
6210 6:55 am 10:25 am Jul 22 - Aug 12
216 7:10 am 10:40 am Jul 23 - Aug 14
218 9:05 am 12:35 pm Aug 15 - Sep 30
218 9:10 am 12:40 pm Jul 23 - Aug 14
228 10:55 am 2:25 pm Jul 22 - Aug 12
230 1:45 pm 5:15 pm Jul 22 - Aug 12
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

We compile tonnes 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 can'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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$333
Destination

Cancun
$333