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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: Thu Jan 8 2015 Return: Wed Jan 14 2015 Trip spans 7 days
Delta
Delta
MDW
7:30a
CUN
1:43p
6h 13m
1 stop
CUN
7:02a
MDW
1:50p
6h 48m
1 stop
Depart: Fri Jan 9 2015 Return: Thu Jan 15 2015 Trip spans 7 days
Delta
Delta
MDW
8:40a
CUN
2:48p
6h 08m
1 stop
CUN
7:02a
MDW
1:50p
6h 48m
1 stop
Depart: Sat Jan 10 2015 Return: Wed Jan 14 2015 Trip spans 5 days
Delta
Delta
MDW
7:30a
CUN
1:43p
6h 13m
1 stop
CUN
7:02a
MDW
1:50p
6h 48m
1 stop
Depart: Sun Jan 11 2015 Return: Thu Jan 15 2015 Trip spans 5 days
Delta
Delta
MDW
7:05a
CUN
2:48p
7h 43m
1 stop
CUN
7:02a
MDW
1:50p
6h 48m
1 stop
Depart: Mon Jan 12 2015 Return: Wed Jan 14 2015 Trip spans 3 days
Delta
Delta
MDW
7:05a
CUN
2:48p
7h 43m
1 stop
CUN
7:02a
MDW
1:50p
6h 48m
1 stop
Depart: Tue Jan 13 2015 Return: Wed Jan 21 2015 Trip spans 9 days
Delta
Delta
MDW
1:00a
CUN
6:26a
5h 26m
1 stop
CUN
3:10a
MDW
9:40a
6h 30m
1 stop
Depart: Wed Jan 14 2015 Return: Sun Jan 18 2015 Trip spans 5 days
Delta
Delta
MDW
4:19a
CUN
12:17p
7h 58m
1 stop
CUN
1:07p
MDW
3:44a
14h 37m
1 stop
Depart: Fri Jan 16 2015 Return: Sun Jan 18 2015 Trip spans 3 days
Delta
Delta
MDW
12:59p
CUN
5:11a
16h 12m
1 stop
CUN
7:40a
MDW
3:00p
7h 20m
1 stop
Depart: Sat Jan 17 2015 Return: Tue Jan 20 2015 Trip spans 4 days
Delta
Delta
MDW
7:46a
CUN
1:33p
5h 47m
1 stop
CUN
1:07p
MDW
3:44a
14h 37m
1 stop
Depart: Sun Jan 18 2015 Return: Thu Jan 22 2015 Trip spans 5 days
Delta
Delta
MDW
2:10a
CUN
2:48p
12h 38m
1 stop
CUN
7:02a
MDW
1:50p
6h 48m
1 stop
Depart: Mon Jan 19 2015 Return: Sat Jan 24 2015 Trip spans 6 days
Delta
Delta
MDW
1:30a
CUN
8:14a
6h 44m
1 stop
CUN
1:07p
MDW
5:34a
16h 27m
1 stop
Depart: Tue Jan 20 2015 Return: Sun Jan 25 2015 Trip spans 6 days
Delta
Delta
MDW
1:00a
CUN
6:26a
5h 26m
1 stop
CUN
2:00a
MDW
8:05a
6h 05m
1 stop
Depart: Wed Jan 21 2015 Return: Wed Jan 28 2015 Trip spans 8 days
Delta
Delta
MDW
2:10a
CUN
2:48p
12h 38m
1 stop
CUN
7:02a
MDW
1:50p
6h 48m
1 stop
Depart: Thu Jan 22 2015 Return: Mon Jan 26 2015 Trip spans 5 days
Delta
Delta
MDW
8:40a
CUN
2:48p
6h 08m
1 stop
CUN
10:00a
MDW
4:34p
6h 34m
1 stop
Depart: Sat Jan 24 2015 Return: Wed Jan 28 2015 Trip spans 5 days
Delta
Delta
MDW
7:30a
CUN
1:33p
6h 03m
1 stop
CUN
7:26a
MDW
2:55p
7h 29m
1 stop
Depart: Sun Jan 25 2015 Return: Wed Jan 28 2015 Trip spans 4 days
Delta
Delta
MDW
8:40a
CUN
2:48p
6h 08m
1 stop
CUN
6:01a
MDW
12:18p
6h 17m
1 stop
Depart: Mon Jan 26 2015 Return: Wed Jan 28 2015 Trip spans 3 days
Delta
Delta
MDW
1:00a
CUN
6:26a
5h 26m
1 stop
CUN
3:10a
MDW
9:40a
6h 30m
1 stop
Depart: Tue Jan 27 2015 Return: Wed Jan 28 2015 Trip spans 2 days
Delta
Delta
MDW
1:00a
CUN
6:26a
5h 26m
1 stop
CUN
3:10a
MDW
9:40a
6h 30m
1 stop
Depart: Thu Jan 15 2015 Return: Thu Jan 22 2015 Trip spans 8 days
Sun Country Air
Sun Country Air
MDW
1:35p
CUN
5:05a
15h 30m
1 stop
CUN
9:20a
MDW
4:05a
18h 45m
2 stops
Depart: Wed Dec 24 2014 Return: Mon Dec 29 2014 Trip spans 6 days
Frontier
Frontier
MDW
1:45p
CUN
10:35a
20h 50m
1 stop
CUN
11:25a
MDW
6:44a
19h 19m
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
216 7:00 am 11:00 am Dec 18 - Jan 4
218 8:55 am 12:55 pm Jan 6 - Mar 6
218 9:00 am 12:55 pm Jan 5 - Jan 5
218 9:05 am 1:00 pm Dec 18 - Jan 2
218 9:05 am 1:00 pm Jan 3 - Jan 4
228 9:10 am 1:05 pm Dec 20 - Dec 27
228 9:50 am 1:50 pm Jan 17 - Feb 28
228 11:10 am 3:10 pm Jan 10 - Jan 10
4940 2:55 pm 6:50 pm Jan 3 - Jan 3
Airports
Origin

Chicago
$436
Destination

Cancun
$436