Find Deals on Flights from Chicago Midway to Mexico

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

Book cheap flights from Chicago Midway to Mexico

(Round-trip)
Depart: Fri Jan 20 2017 Return: Sat Feb 11 2017 Trip spans 23 days
Delta
Delta
MDW
1:00a
MEX
7:43a
6h 43m
1 stop
MEX
2:12a
MDW
10:01a
7h 49m
1 stop
Depart: Fri Feb 3 2017 Return: Mon Feb 6 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
2:35a
CUN
1:45a
23h 10m
1 stop
CUN
8:45p
MDW
2:45a
6h 00m
1 stop
Depart: Tue Jan 17 2017 Return: Tue Jan 24 2017 Trip spans 8 days
Volaris
Volaris
MDW
7:15a
DGO
11:36a
4h 21m
nonstop
DGO
2:04a
MDW
5:42a
3h 38m
nonstop
Depart: Thu Feb 9 2017 Return: Sun Feb 12 2017 Trip spans 4 days
Delta
Delta
MDW
9:08a
MEX
5:13p
8h 05m
1 stop
MEX
3:55a
MDW
12:22p
8h 27m
1 stop
Depart: Mon Dec 12 2016 Return: Tue Dec 20 2016 Trip spans 9 days
Major Airline
Major Airline
MDW
9:10p
CUN
4:02a
6h 52m
1 stop
CUN
5:55a
MDW
1:21p
7h 26m
1 stop
Depart: Wed Feb 22 2017 Return: Wed Mar 1 2017 Trip spans 8 days
Delta
Delta
MDW
7:15a
MEX
2:30p
7h 15m
1 stop
MEX
8:05a
MDW
5:13p
9h 08m
1 stop
Depart: Sat Jan 21 2017 Return: Tue Jan 24 2017 Trip spans 4 days
Volaris
Volaris
MDW
7:15a
DGO
11:36a
4h 21m
nonstop
DGO
2:04a
MDW
5:42a
3h 38m
nonstop
Depart: Tue Jan 24 2017 Return: Sat Jan 28 2017 Trip spans 5 days
Volaris
Volaris
MDW
7:15a
DGO
11:36a
4h 21m
nonstop
DGO
2:04a
MDW
5:42a
3h 38m
nonstop
Depart: Mon Dec 5 2016 Return: Mon Dec 12 2016 Trip spans 8 days
Volaris
Volaris
MDW
12:48p
GDL
5:40p
4h 52m
nonstop
GDL
2:23a
MDW
6:27a
4h 04m
nonstop
Depart: Sun Mar 19 2017 Return: Thu Mar 23 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
10:00p
CUN
6:07a
8h 07m
2 stops
CUN
10:45p
MDW
6:44a
7h 59m
2 stops
Depart: Fri Jan 13 2017 Return: Sat Jan 21 2017 Trip spans 9 days
Delta
Delta
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
CUN
2:37p
MDW
6:28a
15h 51m
1 stop
Depart: Wed Mar 1 2017 Return: Wed Mar 8 2017 Trip spans 8 days
Volaris
Volaris
MDW
12:50p
GDL
5:27p
4h 37m
nonstop
GDL
2:30a
MDW
6:27a
3h 57m
nonstop
Depart: Sun Feb 5 2017 Return: Sat Feb 11 2017 Trip spans 7 days
Delta
Delta
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
CUN
1:45a
MDW
11:01a
9h 16m
1 stop
Depart: Thu Mar 2 2017 Return: Thu Mar 9 2017 Trip spans 8 days
Volaris
Volaris
MDW
12:50p
GDL
5:27p
4h 37m
nonstop
GDL
2:30a
MDW
6:27a
3h 57m
nonstop
Depart: Wed Jan 25 2017 Return: Sat Jan 28 2017 Trip spans 4 days
Delta
Delta
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
CUN
1:45a
MDW
9:01a
7h 16m
1 stop
Depart: Wed Apr 5 2017 Return: Wed Apr 12 2017 Trip spans 8 days
Major Airline
Major Airline
MDW
10:00p
GDL
12:27p
14h 27m
nonstop
GDL
11:00p
MDW
6:44a
7h 44m
nonstop
Depart: Fri Mar 3 2017 Return: Tue Mar 7 2017 Trip spans 5 days
Volaris
Volaris
MDW
12:50p
GDL
5:27p
4h 37m
nonstop
GDL
2:30a
MDW
6:27a
3h 57m
nonstop
Depart: Tue Jan 31 2017 Return: Sat Feb 4 2017 Trip spans 5 days
Delta
Delta
MDW
9:08a
CUN
3:00p
5h 52m
1 stop
CUN
3:30a
MDW
11:01a
7h 31m
1 stop
Depart: Sun Apr 9 2017 Return: Sun Apr 16 2017 Trip spans 8 days
Major Airline
Major Airline
MDW
10:00p
GDL
12:27p
14h 27m
1 stop
GDL
11:00p
MDW
2:09p
15h 09m
1 stop
Depart: Sat Mar 4 2017 Return: Sat Mar 11 2017 Trip spans 8 days
Volaris
Volaris
MDW
12:50p
GDL
5:27p
4h 37m
nonstop
GDL
2:30a
MDW
6:27a
3h 57m
nonstop
* 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

Chicago
$225
Destination

Cancun
$228
Durango
$251
Guadalajara
$262
Mexico City
$225