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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 Jul 18 2015 Return: Sat Jul 25 2015 Trip spans 8 days
Volaris
Volaris
MDW
1:50p
CUN
4:25a
14h 35m
1 stop
CUN
4:20p
MDW
7:15a
14h 55m
1 stop
Depart: Sat Jul 25 2015 Return: Sat Aug 1 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 Jul 11 2015 Return: Sat Jul 18 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: Fri Apr 3 2015 Return: Sat Apr 11 2015 Trip spans 9 days
Sun Country Air
Sun Country Air
MDW
5:20a
CUN
2:45p
33h 25m
1 stop
CUN
4:40p
MDW
5:40a
37h 00m
1 stop
Depart: Thu Apr 9 2015 Return: Sat Apr 18 2015 Trip spans 10 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
Depart: Tue May 5 2015 Return: Sun May 10 2015 Trip spans 6 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
Depart: Tue May 26 2015 Return: Sun May 31 2015 Trip spans 6 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
8:45a
28h 45m
2 stops
CUN
6:55a
MDW
4:45p
9h 50m
1 stop
Depart: Mon Apr 6 2015 Return: Sat Apr 11 2015 Trip spans 6 days
Sun Country Air
Sun Country Air
MDW
5:20a
CUN
2:45p
9h 25m
1 stop
CUN
4:40p
MDW
1:45p
21h 05m
1 stop
Depart: Thu May 14 2015 Return: Mon May 18 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
8:45a
28h 45m
2 stops
CUN
9:30a
MDW
4:45p
31h 15m
2 stops
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
Depart: Thu Apr 30 2015 Return: Sun May 3 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MDW
6:30a
CUN
8:45a
26h 15m
2 stops
CUN
6:55a
MDW
4:45p
9h 50m
1 stop
Depart: Fri Apr 17 2015 Return: Sun Apr 26 2015 Trip spans 10 days
Sun Country Air
Sun Country Air
MDW
6:30a
CUN
8:40a
26h 10m
1 stop
CUN
9:30a
MDW
5:40a
20h 10m
1 stop
Depart: Fri Apr 24 2015 Return: Mon Apr 27 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MDW
6:30a
CUN
8:40a
26h 10m
1 stop
CUN
10:20a
MDW
1:45p
27h 25m
2 stops
Depart: Fri May 8 2015 Return: Sun May 10 2015 Trip spans 3 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
6:05a
26h 05m
1 stop
CUN
9:30a
MDW
5:40a
20h 10m
2 stops
Depart: Tue May 12 2015 Return: Sat May 16 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MDW
4:00a
CUN
6:05a
26h 05m
1 stop
CUN
9:30a
MDW
4:45p
31h 15m
2 stops
Depart: Thu Apr 2 2015 Return: Sat Apr 11 2015 Trip spans 10 days
Sun Country Air
Sun Country Air
MDW
2:35p
CUN
8:40a
18h 05m
1 stop
CUN
4:40p
MDW
1:45p
21h 05m
1 stop
Depart: Sat Feb 14 2015 Return: Wed Feb 25 2015 Trip spans 12 days
Delta
Delta
MDW
7:30a
CUN
2:52p
7h 22m
1 stop
CUN
6:52a
MDW
1:55p
7h 03m
1 stop
Depart: Sun Feb 15 2015 Return: Thu Feb 19 2015 Trip spans 5 days
Delta
Delta
MDW
2:05a
CUN
10:40a
8h 35m
1 stop
CUN
6:52a
MDW
1:55p
7h 03m
1 stop
Depart: Mon Feb 16 2015 Return: Wed Feb 25 2015 Trip spans 10 days
Delta
Delta
MDW
1:00a
CUN
6:26a
5h 26m
1 stop
CUN
6:10a
MDW
12:24p
6h 14m
1 stop
Depart: Tue Feb 17 2015 Return: Thu Feb 19 2015 Trip spans 3 days
Delta
Delta
MDW
1:00a
CUN
6:26a
5h 26m
1 stop
CUN
3:15a
MDW
9:39a
6h 24m
1 stop
Change your search
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
218 8:55 am 12:55 pm Jan 19 - Mar 6
228 9:50 am 1:50 pm Jan 24 - Feb 28
Airports
Origin

Chicago
$409
Destination

Cancun
$409