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Find Flight Deals 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 1 2015 Return: Tue Aug 4 2015 Trip spans 4 days
Volaris
Volaris
MDW
1:50p
CUN
3:25a
13h 35m
1 stop
CUN
7:30a
MDW
5:40p
10h 10m
1 stop
Depart: Sat Aug 8 2015 Return: Sat Aug 15 2015 Trip spans 8 days
Volaris
Volaris
MDW
1:50p
CUN
3:25a
13h 35m
1 stop
CUN
4:30p
MDW
7:17a
14h 47m
1 stop
Depart: Sat May 9 2015 Return: Sat May 16 2015 Trip spans 8 days
Delta
Delta
MDW
3:00a
CUN
12:14p
9h 14m
2 stops
CUN
7:20a
MDW
6:07p
10h 47m
2 stops
Depart: Sat Jul 25 2015 Return: Tue Aug 11 2015 Trip spans 18 days
Volaris
Volaris
MDW
1:50p
CUN
3:25a
13h 35m
1 stop
CUN
7:30a
MDW
5:40p
10h 10m
1 stop
Depart: Tue Apr 7 2015 Return: Wed Apr 15 2015 Trip spans 9 days
Delta
Delta
MDW
3:05a
CUN
3:47p
12h 42m
1 stop
CUN
2:58a
MDW
11:25a
8h 27m
1 stop
Depart: Wed Apr 8 2015 Return: Wed Apr 15 2015 Trip spans 8 days
Delta
Delta
MDW
10:30a
CUN
3:47p
5h 17m
1 stop
CUN
2:58a
MDW
9:55a
6h 57m
1 stop
Depart: Sun Apr 12 2015 Return: Thu Apr 16 2015 Trip spans 5 days
Delta
Delta
MDW
8:18a
CUN
3:47p
7h 29m
1 stop
CUN
9:55a
MDW
3:54p
5h 59m
1 stop
Depart: Mon Apr 13 2015 Return: Fri Apr 17 2015 Trip spans 5 days
Delta
Delta
MDW
5:53a
CUN
11:32a
5h 39m
1 stop
CUN
2:58a
MDW
9:55a
6h 57m
1 stop
Depart: Tue Apr 14 2015 Return: Fri Apr 17 2015 Trip spans 4 days
Delta
Delta
MDW
3:00a
CUN
9:00a
6h 00m
1 stop
CUN
2:58a
MDW
9:55a
6h 57m
1 stop
Depart: Sun Apr 19 2015 Return: Tue Apr 21 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
7:28a
5h 28m
1 stop
CUN
4:05a
MDW
11:25a
7h 20m
1 stop
Depart: Mon Apr 20 2015 Return: Thu Apr 23 2015 Trip spans 4 days
Delta
Delta
MDW
10:30a
CUN
3:47p
5h 17m
1 stop
CUN
7:03a
MDW
1:21p
6h 18m
1 stop
Depart: Tue Apr 21 2015 Return: Thu Apr 23 2015 Trip spans 3 days
Delta
Delta
MDW
10:30a
CUN
3:47p
5h 17m
1 stop
CUN
7:03a
MDW
1:21p
6h 18m
1 stop
Depart: Wed Apr 22 2015 Return: Thu Apr 23 2015 Trip spans 2 days
Delta
Delta
MDW
10:30a
CUN
3:47p
5h 17m
1 stop
CUN
7:03a
MDW
1:21p
6h 18m
1 stop
Depart: Wed Apr 29 2015 Return: Tue May 5 2015 Trip spans 7 days
Delta
Delta
MDW
3:00a
CUN
9:00a
6h 00m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Sun May 3 2015 Return: Wed May 6 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
7:25a
5h 25m
1 stop
CUN
11:00a
MDW
6:09p
7h 09m
1 stop
Depart: Mon May 4 2015 Return: Thu May 7 2015 Trip spans 4 days
Delta
Delta
MDW
6:00a
CUN
11:32a
5h 32m
1 stop
CUN
4:08a
MDW
11:24a
7h 16m
1 stop
Depart: Tue May 5 2015 Return: Thu May 7 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
7:25a
5h 25m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Wed May 6 2015 Return: Wed May 13 2015 Trip spans 8 days
Delta
Delta
MDW
2:45a
CUN
9:05a
6h 20m
1 stop
CUN
9:45a
MDW
3:58p
6h 13m
1 stop
Depart: Mon May 11 2015 Return: Wed May 13 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
7:25a
5h 25m
1 stop
CUN
9:45a
MDW
3:58p
6h 13m
1 stop
Depart: Thu Apr 23 2015 Return: Mon Apr 27 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MDW
2:35p
CUN
9:35a
19h 00m
2 stops
CUN
10:20a
MDW
1:45p
27h 25m
2 stops
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 7:00 am 10:50 am Mar 8 - Apr 6
216 7:00 am 10:45 am Apr 8 - Jun 6
216 7:10 am 10:50 am Apr 7 - Apr 7
218 8:55 am 12:40 pm Apr 8 - Aug 8
218 9:00 am 12:50 pm Mar 8 - Apr 6
218 9:10 am 12:50 pm Apr 7 - Apr 7
220 10:35 am 2:25 pm Mar 8 - Apr 7
220 10:40 am 2:25 pm Apr 11 - Jun 6
4944 12:15 pm 4:05 pm Mar 14 - Apr 4
Airports
Origin

Chicago
$468
Destination

Cancun
$468