$149 Cheap Southwest Airlines flights Cancun (CUN) to Chicago (MDW)

Scoring cheap one-way Southwest Airlines flights from CUN to MDW from $149 on Expedia couldn't be simpler --- just filter by "Price (lowest to highest)." Alternatively, check out our budget-friendly round-trip fares from $273 for your next exciting adventure.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

To get cheap flights from CUN to MDW with Southwest Airlines, begin searching about one month before your intended departure. You can save 17% when you lock in your international tickets 18 to 29 days ahead instead of booking four to five months in advance. Another helpful tip? Booking on Sunday can lead to average savings of 17% compared to Friday (the most expensive day).**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

The earliest flight from CUN to MDW with Southwest Airlines leaves at 10:50AM UTC-5. You'll land at 1:45PM UTC-6. The final Southwest Airlines flight of the day leaves at 3:00PM UTC-5 and arrives at 5:50PM UTC-6. With approximately 20% fewer cancellations for early and mid-morning flights, beginning your travel day early is usually the best way to go.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.