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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 22 2015 Return: Sat Aug 29 2015 Trip spans 8 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 29 2015 Return: Sat Sep 5 2015 Trip spans 8 days
Volaris
Volaris
MDW
1:50p
CUN
4:25a
14h 35m
1 stop
CUN
7:30a
MDW
5:40p
10h 10m
1 stop
Depart: Tue May 26 2015 Return: Wed May 27 2015 Trip spans 2 days
Delta
Delta
MDW
8:22a
CUN
3:42p
7h 20m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Thu May 7 2015 Return: Sat May 9 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
11:32a
9h 32m
1 stop
CUN
5:55a
MDW
6:08p
12h 13m
1 stop
Depart: Fri May 8 2015 Return: Tue May 12 2015 Trip spans 5 days
Delta
Delta
MDW
3:00a
CUN
3:42p
12h 42m
1 stop
CUN
4:08a
MDW
11:24a
7h 16m
1 stop
Depart: Sat May 9 2015 Return: Tue May 12 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
3:42p
13h 42m
1 stop
CUN
4:08a
MDW
6:10p
14h 02m
1 stop
Depart: Sun May 10 2015 Return: Tue May 12 2015 Trip spans 3 days
Delta
Delta
MDW
3:00a
CUN
11:32a
8h 32m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Mon May 11 2015 Return: Wed May 13 2015 Trip spans 3 days
Delta
Delta
MDW
3:00a
CUN
11:32a
8h 32m
1 stop
CUN
9:45a
MDW
3:59p
6h 14m
1 stop
Depart: Tue May 12 2015 Return: Thu May 14 2015 Trip spans 3 days
Delta
Delta
MDW
3:00a
CUN
3:42p
12h 42m
1 stop
CUN
9:45a
MDW
6:10p
8h 25m
1 stop
Depart: Wed May 13 2015 Return: Sat May 16 2015 Trip spans 4 days
Delta
Delta
MDW
3:00a
CUN
11:32a
8h 32m
1 stop
CUN
3:00a
MDW
3:57p
12h 57m
1 stop
Depart: Thu May 14 2015 Return: Sat May 16 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
3:42p
13h 42m
1 stop
CUN
7:00a
MDW
6:08p
11h 08m
1 stop
Depart: Fri May 15 2015 Return: Tue May 19 2015 Trip spans 5 days
Delta
Delta
MDW
2:00a
CUN
3:42p
13h 42m
1 stop
CUN
9:45a
MDW
3:59p
6h 14m
1 stop
Depart: Sat May 16 2015 Return: Tue May 19 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
3:42p
13h 42m
1 stop
CUN
11:00a
MDW
6:10p
7h 10m
1 stop
Depart: Sun May 17 2015 Return: Tue May 19 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
CUN
3:42p
13h 42m
1 stop
CUN
7:00a
MDW
6:10p
11h 10m
1 stop
Depart: Tue May 19 2015 Return: Thu May 21 2015 Trip spans 3 days
Delta
Delta
MDW
3:00a
CUN
3:42p
12h 42m
1 stop
CUN
3:00a
MDW
9:51a
6h 51m
1 stop
Depart: Wed May 20 2015 Return: Sat May 23 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
3:42p
13h 42m
1 stop
CUN
3:00a
MDW
3:57p
12h 57m
1 stop
Depart: Mon May 25 2015 Return: Thu May 28 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
CUN
3:42p
13h 42m
1 stop
CUN
4:08a
MDW
1:24p
9h 16m
1 stop
Depart: Wed May 27 2015 Return: Fri May 29 2015 Trip spans 3 days
Delta
Delta
MDW
6:00a
CUN
3:42p
9h 42m
1 stop
CUN
3:00a
MDW
11:24a
8h 24m
1 stop
Depart: Fri May 29 2015 Return: Mon Jun 1 2015 Trip spans 4 days
Delta
Delta
MDW
3:00a
CUN
3:42p
12h 42m
1 stop
CUN
3:00a
MDW
11:24a
8h 24m
1 stop
Depart: Wed Jul 8 2015 Return: Sat Jul 11 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
12:30p
56h 30m
2 stops
CUN
6:55a
MDW
4:45p
33h 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 2 - Jun 6
216 7:00 am 10:45 am May 3 - Jun 5
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 2 - Jun 6
6900 10:40 am 2:25 pm Jun 7 - Aug 8
220 12:25 pm 4:10 pm May 2 - Jun 6
220 1:45 pm 5:15 pm Jun 7 - Jun 26
Airports
Origin

Chicago
$437
Destination

Cancun
$437