Direct flights from Chicago to Cancun
All flights from MDW to CUN non-stop. There are direct flights from Chicago Midway International, Illinois, USA to Cancun International Airport (CUN), Mexico every day of the week with Southwest Airlines. The flight distance is 1442 miles and the trip usually takes about 3 hours and 40 minutes.
Airlines with non-stop routes:

Southwest Airlines

Frontier Airlines
No flights anymore
Flight schedule from Chicago to Cancun with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2025-04-22
Chicago to Cancun flight departures
Select a date to see all scheduled flight departures between MDW to CUN.
MDW - CUN information
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Distance1442 miles (2320 km)
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Flight time3 hours and 40 minutes
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Airlines
Southwest
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AlliancesOne WorldSky TeamStar Alliance
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ClassesEconomyBusinessFirst Class
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Southwest AircraftBoeing 737 Passenger
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Arrival TerminalTerminal 4 (Southwest)
Direct flights from Chicago to Mexico

From Chicago to San Jose Cabo
SJD Los Cabos International

From Chicago to Guadalajara
GDL Guadalajara International Airport

From Chicago to Leon/Guanajuato
BJX Guanajuato

From Chicago to Morelia
MLM General Francisco J Mujica

From Chicago to Aguascalientes
AGU Jesus Teran International

From Chicago to Zacatecas
ZCL La Calera Airport

From Chicago to Durango
DGO Durango International