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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: Tue Apr 21 2015 Return: Wed Apr 22 2015 Trip spans 2 days
Delta
Delta
MDW
8:18a
CUN
3:47p
7h 29m
1 stop
CUN
2:58a
MDW
9:55a
6h 57m
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
2:58a
MDW
9:55a
6h 57m
1 stop
Depart: Fri Apr 24 2015 Return: Sat Apr 25 2015 Trip spans 2 days
Delta
Delta
MDW
10:30a
CUN
3:47p
5h 17m
1 stop
CUN
2:58a
MDW
10:55a
7h 57m
1 stop
Depart: Tue Apr 14 2015 Return: Wed Apr 15 2015 Trip spans 2 days
Delta
Delta
MDW
10:30a
CUN
3:47p
5h 17m
1 stop
CUN
9:55a
MDW
3:54p
5h 59m
1 stop
Depart: Fri Apr 17 2015 Return: Sat Apr 18 2015 Trip spans 2 days
Delta
Delta
MDW
10:30a
CUN
3:47p
5h 17m
1 stop
CUN
4:05a
MDW
10:55a
6h 50m
1 stop
Depart: Sat Apr 18 2015 Return: Mon Apr 20 2015 Trip spans 3 days
Delta
Delta
MDW
8:35a
CUN
2:42p
6h 07m
1 stop
CUN
2:58a
MDW
3:54p
12h 56m
1 stop
Depart: Sun Apr 19 2015 Return: Tue Apr 21 2015 Trip spans 3 days
Delta
Delta
MDW
5:50a
CUN
3:47p
9h 57m
1 stop
CUN
8:29a
MDW
3:54p
7h 25m
1 stop
Depart: Mon Apr 20 2015 Return: Wed Apr 22 2015 Trip spans 3 days
Delta
Delta
MDW
5:50a
CUN
11:32a
5h 42m
1 stop
CUN
9:56a
MDW
5:17p
7h 21m
1 stop
Depart: Thu Apr 23 2015 Return: Sat Apr 25 2015 Trip spans 3 days
Delta
Delta
MDW
3:05a
CUN
3:47p
12h 42m
1 stop
CUN
2:58a
MDW
10:55a
7h 57m
1 stop
Depart: Sat Apr 25 2015 Return: Tue Apr 28 2015 Trip spans 4 days
Delta
Delta
MDW
5:20a
CUN
2:42p
9h 22m
1 stop
CUN
8:29a
MDW
3:54p
7h 25m
1 stop
Depart: Sun Apr 26 2015 Return: Tue Apr 28 2015 Trip spans 3 days
Delta
Delta
MDW
5:50a
CUN
3:47p
9h 57m
1 stop
CUN
8:29a
MDW
3:54p
7h 25m
1 stop
Depart: Mon Apr 27 2015 Return: Wed Apr 29 2015 Trip spans 3 days
Delta
Delta
MDW
3:05a
CUN
10:00a
6h 55m
1 stop
CUN
2:58a
MDW
11:25a
8h 27m
1 stop
Depart: Tue Apr 28 2015 Return: Thu Apr 30 2015 Trip spans 3 days
Delta
Delta
MDW
8:18a
CUN
3:47p
7h 29m
1 stop
CUN
4:05a
MDW
1:21p
9h 16m
1 stop
Depart: Wed Apr 29 2015 Return: Fri May 1 2015 Trip spans 3 days
Delta
Delta
MDW
3:05a
CUN
10:00a
6h 55m
1 stop
CUN
3:00a
MDW
11:24a
8h 24m
1 stop
Depart: Fri May 1 2015 Return: Tue May 5 2015 Trip spans 5 days
Delta
Delta
MDW
8:22a
CUN
3:42p
7h 20m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Sat May 2 2015 Return: Tue May 5 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
11:32a
9h 32m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Sun May 3 2015 Return: Tue May 5 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
11:32a
9h 32m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Mon May 4 2015 Return: Wed May 6 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
8:38a
6h 38m
1 stop
CUN
3:00a
MDW
1:24p
10h 24m
1 stop
Depart: Tue May 5 2015 Return: Thu May 7 2015 Trip spans 3 days
Delta
Delta
MDW
8:22a
CUN
3:42p
7h 20m
1 stop
CUN
11:00a
MDW
6:09p
7h 09m
1 stop
Depart: Fri Aug 7 2015 Return: Wed Aug 12 2015 Trip spans 6 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
6:05a
26h 05m
1 stop
CUN
9:40a
MDW
4:45p
31h 05m
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
4949 5:15 am 9:00 am Apr 11 - Jun 6
216 7:00 am 10:45 am Apr 8 - Jun 5
216 7:10 am 10:50 am Apr 7 - Apr 7
218 9:10 am 12:50 pm Apr 7 - Apr 7
218 9:20 am 1:05 pm Apr 8 - Jun 6
220 11:40 am 3:30 pm Apr 5 - Apr 7
220 12:25 pm 4:10 pm Apr 11 - Jun 6
Airports
Origin

Chicago
$477
Destination

Cancun
$477