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

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

Book cheap flights from Chicago Midway to Cancun

(Round-trip)
Depart: Sat Aug 29 2015 Return: Tue Sep 1 2015 Trip spans 4 days
Volaris
Volaris
MDW
1:50p
CUN
4:25a
14h 35m
1 stop
CUN
7:30a
MDW
5:40p
10h 10m
1 stop
Depart: Sat Aug 22 2015 Return: Sat Aug 29 2015 Trip spans 8 days
Volaris
Volaris
MDW
1:50p
CUN
4:25a
14h 35m
1 stop
CUN
4:30p
MDW
7:17a
14h 47m
1 stop
Depart: Sat Aug 15 2015 Return: Sat Aug 22 2015 Trip spans 8 days
Volaris
Volaris
MDW
1:50p
CUN
4:25a
14h 35m
1 stop
CUN
4:30p
MDW
7:17a
14h 47m
1 stop
Depart: Sat Aug 8 2015 Return: Tue Aug 11 2015 Trip spans 4 days
Volaris
Volaris
MDW
1:50p
CUN
4:25a
14h 35m
1 stop
CUN
7:30a
MDW
5:40p
10h 10m
1 stop
Depart: Fri Jun 19 2015 Return: Mon Jun 22 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
3:39p
13h 39m
1 stop
CUN
7:00a
MDW
2:53p
7h 53m
1 stop
Depart: Sat Jun 20 2015 Return: Mon Jun 22 2015 Trip spans 3 days
Delta
Delta
MDW
8:00a
CUN
3:39p
7h 39m
1 stop
CUN
3:00a
MDW
11:09a
8h 09m
1 stop
Depart: Sun Jun 21 2015 Return: Tue Jun 23 2015 Trip spans 3 days
Delta
Delta
MDW
3:10a
CUN
3:39p
12h 29m
1 stop
CUN
3:00a
MDW
2:53p
11h 53m
1 stop
Depart: Mon Jun 22 2015 Return: Wed Jun 24 2015 Trip spans 3 days
Delta
Delta
MDW
3:10a
CUN
3:39p
12h 29m
1 stop
CUN
3:00a
MDW
2:53p
11h 53m
1 stop
Depart: Tue Jun 23 2015 Return: Thu Jun 25 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
3:39p
13h 39m
1 stop
CUN
3:00a
MDW
2:53p
11h 53m
1 stop
Depart: Wed Jun 24 2015 Return: Wed Jul 1 2015 Trip spans 8 days
Delta
Delta
MDW
2:00a
CUN
3:39p
13h 39m
1 stop
CUN
4:12a
MDW
1:37p
9h 25m
1 stop
Depart: Fri Jun 26 2015 Return: Wed Jul 1 2015 Trip spans 6 days
Delta
Delta
MDW
9:50a
CUN
3:39p
5h 49m
1 stop
CUN
10:59a
MDW
6:14p
7h 15m
1 stop
Depart: Sat Jun 27 2015 Return: Wed Jul 1 2015 Trip spans 5 days
Delta
Delta
MDW
2:35a
CUN
9:06a
6h 31m
1 stop
CUN
4:12a
MDW
6:14p
14h 02m
1 stop
Depart: Mon Jun 29 2015 Return: Wed Jul 1 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
3:39p
13h 39m
1 stop
CUN
3:00a
MDW
9:18a
6h 18m
1 stop
Depart: Tue Jun 30 2015 Return: Fri Jul 3 2015 Trip spans 4 days
Delta
Delta
MDW
8:29a
CUN
3:39p
7h 10m
1 stop
CUN
3:00a
MDW
6:12p
15h 12m
1 stop
Depart: Thu Jul 2 2015 Return: Mon Jul 6 2015 Trip spans 5 days
Delta
Delta
MDW
2:00a
CUN
3:39p
13h 39m
1 stop
CUN
3:00a
MDW
4:20p
13h 20m
1 stop
Depart: Sat Jul 4 2015 Return: Mon Jul 6 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
3:39p
13h 39m
1 stop
CUN
3:00a
MDW
6:14p
15h 14m
1 stop
Depart: Sun Jul 5 2015 Return: Tue Jul 7 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
3:39p
13h 39m
1 stop
CUN
9:45a
MDW
6:14p
8h 29m
1 stop
Depart: Sat Aug 1 2015 Return: Wed Aug 12 2015 Trip spans 12 days
Delta
Delta
MDW
8:00a
CUN
3:39p
7h 39m
1 stop
CUN
3:00a
MDW
2:52p
11h 52m
1 stop
Depart: Wed Sep 2 2015 Return: Fri Sep 11 2015 Trip spans 10 days
Delta
Delta
MDW
8:30a
CUN
3:46p
7h 16m
1 stop
CUN
3:00a
MDW
9:12a
6h 12m
1 stop
Depart: Fri Oct 2 2015 Return: Sun Oct 4 2015 Trip spans 3 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
6:05a
26h 05m
1 stop
CUN
6:55a
MDW
4:45p
9h 50m
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
4949 5:15 am 9:00 am May 23 - Jun 6
216 7:05 am 10:40 am Jun 7 - Aug 8
218 8:55 am 12:40 pm Jun 8 - Aug 7
218 9:20 am 1:05 pm May 21 - Jun 6
6900 10:40 am 2:25 pm Jun 7 - Aug 8
220 12:25 pm 4:10 pm May 23 - Jun 6
220 1:45 pm 5:15 pm Jun 29 - Jul 7
220 1:45 pm 5:15 pm Jun 7 - Jun 26
6961 2:10 pm 5:40 pm Jun 28 - Jul 5
6955 2:25 pm 5:55 pm Jun 13 - Aug 8
Airports
Origin

Chicago
$359
Destination

Cancun
$359