Southwest® flights from Cancun to Chicago (Midway)

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Explore flights from Cancun to Chicago (Midway)

Flight Details

Departing from:
Cancún International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
3 hours 37 minutes
Distance:
1430 miles

Route Information

113† Weekly flights
  • 1‡ Nonstop flight per day Monday through Friday
  • 2‡ Nonstop flights on Saturday
  • 2‡ Nonstop flights on Sunday

† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

Questions we hear the most

The average flight time from Cancun to Chicago (Midway) is 3 hours 37 minutes.
There are 113 weekly flights from Cancun to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Cancun to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Cancun to Chicago (Midway) 2 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Cancun to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from Cancun to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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