Find Deals on Flights from Chicago Midway 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.
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Book cheap flights from Chicago Midway to Cancun

(Round-trip)
Depart: Tue Oct 20 2015 Return: Tue Oct 27 2015 Trip spans 8 days
Delta
Delta
MDW
5:18a
CUN
3:32p
10h 14m
2 stops
CUN
3:00a
MDW
10:52a
7h 52m
2 stops
Depart: Tue Nov 3 2015 Return: Tue Nov 10 2015 Trip spans 8 days
Delta
Delta
MDW
2:00a
CUN
3:58p
13h 58m
2 stops
CUN
3:00a
MDW
10:53a
7h 53m
2 stops
Depart: Fri Oct 30 2015 Return: Fri Nov 6 2015 Trip spans 8 days
Delta
Delta
MDW
8:38a
CUN
6:58a
22h 20m
2 stops
CUN
7:00a
MDW
4:24a
21h 24m
2 stops
Depart: Tue Sep 22 2015 Return: Tue Sep 29 2015 Trip spans 8 days
Delta
Delta
MDW
5:17a
CUN
3:40p
10h 23m
2 stops
CUN
5:45a
MDW
1:54p
8h 09m
2 stops
Depart: Tue Oct 13 2015 Return: Wed Oct 21 2015 Trip spans 9 days
Delta
Delta
MDW
5:18a
CUN
3:32p
10h 14m
2 stops
CUN
3:00a
MDW
11:52a
8h 52m
2 stops
Depart: Thu Dec 31 2015 Return: Mon Jan 11 2016 Trip spans 12 days
Delta
Delta
MDW
1:35a
CUN
9:10a
7h 35m
1 stop
CUN
3:00a
MDW
8:12a
5h 12m
1 stop
Depart: Sat Jan 2 2016 Return: Mon Jan 11 2016 Trip spans 10 days
Delta
Delta
MDW
2:00a
CUN
10:48a
8h 48m
1 stop
CUN
3:00a
MDW
8:12a
5h 12m
1 stop
Depart: Thu Feb 18 2016 Return: Wed Feb 24 2016 Trip spans 7 days
Delta
Delta
MDW
1:00a
CUN
12:37p
11h 37m
2 stops
CUN
2:00a
MDW
1:29p
11h 29m
1 stop
Depart: Tue Feb 23 2016 Return: Tue Mar 1 2016 Trip spans 8 days
Delta
Delta
MDW
7:30a
CUN
3:46p
8h 16m
1 stop
CUN
3:00a
MDW
11:10a
8h 10m
2 stops
Depart: Tue Nov 17 2015 Return: Wed Nov 18 2015 Trip spans 2 days
Delta
Delta
MDW
8:54a
CUN
3:58p
7h 04m
1 stop
CUN
3:00a
MDW
8:14a
5h 14m
1 stop
Depart: Sat Dec 5 2015 Return: Wed Dec 9 2015 Trip spans 5 days
Delta
Delta
MDW
1:00a
CUN
2:34p
13h 34m
2 stops
CUN
4:54a
MDW
4:32p
11h 38m
2 stops
Depart: Fri Feb 19 2016 Return: Fri Feb 26 2016 Trip spans 8 days
Delta
Delta
MDW
1:45a
CUN
1:15p
11h 30m
1 stop
CUN
2:00a
MDW
8:12a
6h 12m
1 stop
Depart: Mon Mar 14 2016 Return: Thu Mar 17 2016 Trip spans 4 days
Delta
Delta
MDW
9:50a
CUN
4:46p
6h 56m
1 stop
CUN
5:55a
MDW
2:54p
8h 59m
2 stops
Depart: Wed Jan 20 2016 Return: Wed Jan 27 2016 Trip spans 8 days
Delta
Delta
MDW
1:00a
CUN
10:05a
9h 05m
1 stop
CUN
7:10a
MDW
12:14p
5h 04m
1 stop
Depart: Sat Feb 6 2016 Return: Tue Feb 9 2016 Trip spans 4 days
Delta
Delta
MDW
1:00a
CUN
1:36p
12h 36m
1 stop
CUN
8:09a
MDW
3:53p
7h 44m
1 stop
Depart: Mon Nov 16 2015 Return: Tue Nov 24 2015 Trip spans 9 days
Delta
Delta
MDW
1:00a
CUN
10:07a
9h 07m
1 stop
CUN
8:35a
MDW
3:32p
6h 57m
1 stop
Depart: Sat Nov 28 2015 Return: Wed Dec 9 2015 Trip spans 12 days
Delta
Delta
MDW
2:00a
CUN
10:56a
8h 56m
1 stop
CUN
2:00a
MDW
11:10a
9h 10m
2 stops
Depart: Fri Nov 13 2015 Return: Mon Nov 16 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
3:58p
13h 58m
2 stops
CUN
1:59a
MDW
3:32p
13h 33m
2 stops
Depart: Tue Sep 15 2015 Return: Sat Sep 19 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
8:50a
28h 50m
2 stops
CUN
9:40a
MDW
4:45p
31h 05m
2 stops
Depart: Sun Dec 20 2015 Return: Fri Dec 25 2015 Trip spans 6 days
Volaris
Volaris
MDW
12:50p
CUN
2:44a
13h 54m
1 stop
CUN
6:05p
MDW
6:15a
12h 10m
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
218 8:55 am 12:30 pm Aug 30 - Oct 30
228 9:05 am 12:40 pm Sep 5 - Oct 31
230 10:55 am 2:30 pm Sep 5 - Oct 31
Airports
Origin

Chicago
$338
Destination

Cancun
$338