Find Deals on Flights from Cancun to Chicago Midway (CUN - MDW)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Cancun to Chicago Midway

(Round-trip)
Depart: Fri Dec 9 2016 Return: Sat Dec 31 2016 Trip spans 23 days
Delta
Delta
CUN
3:30a
MDW
9:24a
5h 54m
1 stop
MDW
4:17a
CUN
1:43p
9h 26m
1 stop
Depart: Thu Dec 8 2016 Return: Sun Dec 11 2016 Trip spans 4 days
Major Airline
Major Airline
CUN
10:30p
MDW
6:02a
7h 32m
nonstop
MDW
7:59a
CUN
12:22a
16h 23m
nonstop
Depart: Tue Jan 3 2017 Return: Sat Jan 7 2017 Trip spans 5 days
Delta
Delta
CUN
11:20a
MDW
12:47p
25h 27m
1 stop
MDW
5:30a
CUN
2:45p
9h 15m
1 stop
Depart: Thu Jan 12 2017 Return: Sat Jan 21 2017 Trip spans 10 days
Delta
Delta
CUN
11:07a
MDW
6:46p
7h 39m
1 stop
MDW
5:30a
CUN
1:17p
7h 47m
1 stop
Depart: Sat Jan 21 2017 Return: Mon Jan 23 2017 Trip spans 3 days
Major Airline
Major Airline
CUN
10:19p
MDW
7:51a
9h 32m
nonstop
MDW
12:30a
CUN
10:00a
9h 30m
nonstop
Depart: Thu Dec 15 2016 Return: Tue Jan 3 2017 Trip spans 20 days
Delta
Delta
CUN
3:30a
MDW
11:02a
7h 32m
1 stop
MDW
7:47a
CUN
1:43p
5h 56m
1 stop
Depart: Wed Dec 21 2016 Return: Tue Jan 3 2017 Trip spans 14 days
Delta
Delta
CUN
1:30a
MDW
7:45a
6h 15m
1 stop
MDW
7:47a
CUN
1:43p
5h 56m
1 stop
Depart: Thu Dec 22 2016 Return: Sun Jan 8 2017 Trip spans 18 days
Delta
Delta
CUN
8:30a
MDW
4:39p
8h 09m
1 stop
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
Depart: Wed Dec 28 2016 Return: Wed Jan 4 2017 Trip spans 8 days
Delta
Delta
CUN
1:30a
MDW
6:21p
16h 51m
1 stop
MDW
2:00a
CUN
8:20a
6h 20m
1 stop
Depart: Tue Jan 31 2017 Return: Wed Feb 1 2017 Trip spans 2 days
Delta
Delta
CUN
1:45a
MDW
7:45a
6h 00m
1 stop
MDW
9:08a
CUN
2:58p
5h 50m
1 stop
Depart: Fri Feb 3 2017 Return: Mon Feb 6 2017 Trip spans 4 days
Delta
Delta
CUN
3:30a
MDW
11:03a
7h 33m
1 stop
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
Depart: Sun Jan 22 2017 Return: Mon Jan 23 2017 Trip spans 2 days
Delta
Delta
CUN
2:45a
MDW
9:33a
6h 48m
1 stop
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
Depart: Sat Jan 14 2017 Return: Sat Jan 21 2017 Trip spans 8 days
Delta
Delta
CUN
1:45a
MDW
9:01a
7h 16m
1 stop
MDW
8:45a
CUN
3:00p
6h 15m
1 stop
Depart: Tue Jan 10 2017 Return: Sat Jan 21 2017 Trip spans 12 days
Delta
Delta
CUN
1:45a
MDW
7:45a
6h 00m
1 stop
MDW
8:45a
CUN
3:00p
6h 15m
1 stop
Depart: Wed Jan 11 2017 Return: Sat Jan 21 2017 Trip spans 11 days
Delta
Delta
CUN
9:47a
MDW
4:02p
6h 15m
1 stop
MDW
8:45a
CUN
3:00p
6h 15m
1 stop
Depart: Fri Jan 13 2017 Return: Sat Jan 21 2017 Trip spans 9 days
Delta
Delta
CUN
1:45a
MDW
7:45a
6h 00m
1 stop
MDW
8:45a
CUN
3:00p
6h 15m
1 stop
Depart: Tue Dec 27 2016 Return: Tue Jan 3 2017 Trip spans 8 days
Delta
Delta
CUN
2:30a
MDW
10:53a
8h 23m
1 stop
MDW
4:17a
CUN
10:04a
5h 47m
1 stop
Depart: Tue Dec 20 2016 Return: Sun Jan 1 2017 Trip spans 13 days
Delta
Delta
CUN
3:30a
MDW
10:53a
7h 23m
1 stop
MDW
7:47a
CUN
1:43p
5h 56m
1 stop
Depart: Mon Jan 30 2017 Return: Tue Jan 31 2017 Trip spans 2 days
Delta
Delta
CUN
1:45a
MDW
7:45a
6h 00m
1 stop
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
Depart: Sat Dec 31 2016 Return: Tue Jan 3 2017 Trip spans 4 days
Delta
Delta
CUN
11:54a
MDW
4:49a
16h 55m
1 stop
MDW
2:55p
CUN
8:10a
17h 15m
1 stop
Select an airline:  Southwest
Direct flights CUN to MDW on Southwest
Flight # Depart CUN Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
238 8:00 am 10:45 am Jan 8 - Mar 5
217 12:55 pm 3:35 pm Dec 1 - Jan 4
219 3:00 pm 5:40 pm Dec 1 - Jan 4
219 3:00 pm 5:45 pm Jan 5 - Mar 8
219 3:00 pm 5:45 pm Jan 7 - Mar 4
209 4:35 pm 7:15 pm Dec 3 - Dec 31
231 5:00 pm 7:45 pm Jan 7 - Mar 4
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Cancun
$255
Destination

Chicago
$255
Airlines