Southwest Airlines
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United States
Midway International Airport
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Mexico
Cancún International Airport
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Scan through all non-stop flights from Chicago to Cancún. The full flight schedule below gives an overview of all non-stop flights from MDW to CUN, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Cancún is a tropical destination known for its warm climate, with temperatures between 25°C and 30°C (77°F to 86°F) throughout the year. The area is characterized by high humidity and frequent rainfall.
Being located north of the equator, Cancún experiences its dry season from November to April, making this the perfect time to visit. In this period, you can expect mostly dry conditions, while the wet season will see days of rain. Humidity and temperatures are consistently high all year long.
In total there are 2 airlines operating nonstop flights from Chicago MDW to Cancún CUN. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their MDW CUN flight schedule.
Flights from MDW to CUN are operated 10 times a week, with an average of 1 flight per day. Departure times vary between 06:05 - 16:35. The earliest flight departs at 06:05, the last flight departs at 16:35. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Chicago to Cancún takes 3 hours and 50 minutes. The flight distance between Chicago and Cancún is 1,433 miles (or 2,306 km).
There is 1 airport in Cancún: Cancún International Airport (CUN).
There are 10 flights per week flying from Chicago to Cancún (as of April 2026).
3 hours and 50 minutes is the average flight time from Chicago to Cancún.
The distance from Chicago to Cancún is 1,433 miles (2,306 kilometers).
Frontier Airlines and Southwest Airlines are flying nonstop from Chicago to Cancún.
There are no alliances flying direct from Chicago to Cancún at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to Cancún:
The earliest flight departs at 06:05 from Chicago and arrives at 09:50 at Cancún.
The latest flight departs at 16:35 from Chicago and arrives at 20:15 at Cancún.
1,433 miles (2,306 km) · 3h 50m
06:05
09:50
Southwest Airlines
WN 228
Southwest Airlines
Boeing 757
Y
W
J
F
06:10
09:45
Southwest Airlines
WN 228
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:15
12:00
Southwest Airlines
WN 228
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:15
12:00
Southwest Airlines
WN 228
Southwest Airlines
Boeing 757
Y
W
J
F
08:20
12:05
Southwest Airlines
WN 228
Southwest Airlines
Boeing 757
Y
W
J
F
08:30
12:20
Frontier Airlines
F9 235
Frontier Airlines
Airbus A320neo
Y
W
J
F
08:30
12:10
Southwest Airlines
WN 228
Southwest Airlines
Boeing 757
Y
W
J
F
09:35
13:10
Southwest Airlines
WN 218
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:30
14:00
Southwest Airlines
WN 218
Southwest Airlines
Boeing 757
Y
W
J
F
10:40
14:10
Southwest Airlines
WN 218
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:00
14:35
Southwest Airlines
WN 218
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:25
17:00
Southwest Airlines
WN 218
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:05
19:45
Southwest Airlines
WN 218
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:25
20:05
Southwest Airlines
WN 218
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:35
20:15
Southwest Airlines
WN 218
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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