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.
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: Tue Oct 13 2015 Return: Wed Oct 14 2015 Trip spans 2 days
Delta
Delta
MDW
9:50a
CUN
3:30p
5h 40m
1 stop
CUN
3:00a
MDW
10:44a
7h 44m
1 stop
Depart: Tue Sep 8 2015 Return: Wed Sep 9 2015 Trip spans 2 days
Delta
Delta
MDW
9:50a
CUN
3:40p
5h 50m
1 stop
CUN
3:00a
MDW
9:15a
6h 15m
1 stop
Depart: Wed Sep 9 2015 Return: Thu Sep 10 2015 Trip spans 2 days
Delta
Delta
MDW
9:50a
CUN
3:40p
5h 50m
1 stop
CUN
3:00a
MDW
10:45a
7h 45m
1 stop
Depart: Thu Sep 10 2015 Return: Fri Sep 11 2015 Trip spans 2 days
Delta
Delta
MDW
9:50a
CUN
3:40p
5h 50m
1 stop
CUN
3:00a
MDW
9:14a
6h 14m
1 stop
Depart: Wed Aug 5 2015 Return: Thu Aug 6 2015 Trip spans 2 days
Delta
Delta
MDW
8:19a
CUN
3:39p
7h 20m
1 stop
CUN
3:00a
MDW
6:14p
15h 14m
1 stop
Depart: Sun Aug 16 2015 Return: Mon Aug 17 2015 Trip spans 2 days
Delta
Delta
MDW
3:05a
CUN
3:39p
12h 34m
1 stop
CUN
3:00a
MDW
6:14p
15h 14m
1 stop
Depart: Tue Aug 18 2015 Return: Tue Aug 25 2015 Trip spans 8 days
Delta
Delta
MDW
2:00a
CUN
7:20a
5h 20m
1 stop
CUN
10:59a
MDW
6:12p
7h 13m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
Delta
Delta
MDW
2:00a
CUN
7:20a
5h 20m
1 stop
CUN
10:59a
MDW
6:12p
7h 13m
1 stop
Depart: Fri Aug 21 2015 Return: Wed Aug 26 2015 Trip spans 6 days
Delta
Delta
MDW
5:55a
CUN
3:52p
9h 57m
1 stop
CUN
3:00a
MDW
9:05a
6h 05m
1 stop
Depart: Sat Aug 22 2015 Return: Wed Aug 26 2015 Trip spans 5 days
Delta
Delta
MDW
8:00a
CUN
3:52p
7h 52m
1 stop
CUN
3:00a
MDW
9:05a
6h 05m
1 stop
Depart: Sun Aug 23 2015 Return: Thu Aug 27 2015 Trip spans 5 days
Delta
Delta
MDW
3:10a
CUN
10:06a
6h 56m
1 stop
CUN
3:00a
MDW
2:57p
11h 57m
1 stop
Depart: Wed Aug 26 2015 Return: Wed Sep 2 2015 Trip spans 8 days
Delta
Delta
MDW
2:00a
CUN
10:06a
8h 06m
1 stop
CUN
3:00a
MDW
9:15a
6h 15m
1 stop
Depart: Thu Aug 27 2015 Return: Mon Aug 31 2015 Trip spans 5 days
Delta
Delta
MDW
8:19a
CUN
3:52p
7h 33m
1 stop
CUN
3:00a
MDW
9:05a
6h 05m
1 stop
Depart: Fri Aug 28 2015 Return: Tue Sep 1 2015 Trip spans 5 days
Delta
Delta
MDW
3:10a
CUN
3:52p
12h 42m
1 stop
CUN
3:00a
MDW
9:15a
6h 15m
1 stop
Depart: Tue Sep 1 2015 Return: Thu Sep 3 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
7:20a
5h 20m
1 stop
CUN
4:13a
MDW
10:45a
6h 32m
1 stop
Depart: Wed Sep 2 2015 Return: Wed Sep 9 2015 Trip spans 8 days
Delta
Delta
MDW
9:50a
CUN
3:40p
5h 50m
1 stop
CUN
3:00a
MDW
9:15a
6h 15m
1 stop
Depart: Mon Sep 7 2015 Return: Wed Sep 9 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
8:36a
6h 36m
1 stop
CUN
3:00a
MDW
9:15a
6h 15m
1 stop
Depart: Sat Sep 12 2015 Return: Sat Sep 19 2015 Trip spans 8 days
Delta
Delta
MDW
2:35a
CUN
9:04a
6h 29m
1 stop
CUN
9:54a
MDW
5:08p
7h 14m
1 stop
Depart: Sat Sep 19 2015 Return: Thu Sep 24 2015 Trip spans 6 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: Sat Dec 26 2015 Trip spans 7 days
Volaris
Volaris
MDW
12:50p
CUN
2:44a
13h 54m
1 stop
CUN
5:47a
MDW
4:40p
10h 53m
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 7:05 am 10:40 am Jul 25 - Aug 8
218 8:55 am 12:40 pm Jul 27 - Aug 7
218 8:55 am 12:30 pm Aug 9 - Oct 30
228 9:05 am 12:40 pm Aug 15 - Oct 31
6900 10:40 am 2:25 pm Jul 25 - Aug 8
230 10:55 am 2:30 pm Aug 15 - Oct 31
220 1:45 pm 5:15 pm Aug 4 - Aug 7
6955 2:25 pm 5:55 pm Jul 25 - Aug 8
Airports
Origin

Chicago
$462
Destination

Cancun
$462