Skip to main content
Beginning of main content

Cheap Flights from Chicago to Cancun $244.76

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia’s Price Guarantee
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Chicago to Cancun (MDW to CUN)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Cancun (MDW to CUN)

Question : Is price more important than specific travel days for you?
Answer : Monday is your lowest-cost day to fly in December. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.

Question : Is there an alternative to Chicago Midway International Airport (MDW) for getting you to Cancun?
Answer : Luckily for you, there is another airport nearby. O'Hare International Airport (ORD) is 16 miles away, and over the upcoming months, flights are 39% cheaper than those from Chicago Midway International Airport.

Question : How often is the price changing when booking a trip from Chicago Midway International Airport (MDW) to Cancun International Airport (CUN)?
Answer : Prices are fluctuating a lot more for this route than most. Prices tend to be lower the further out you book.

Question : How many different departure times are there each day?
Answer : On average, you can expect five different choices of flight times when you book. The average route has 31 different flight times per day, so expect fewer choices than you're used to.

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : As of December 5th, the cheapest day to fly from Chicago to Cancun is December 19th. Tickets have been sold for 47% below the average price for this route.

Question : Which day has the most flight time options?
Answer : Saturday has the most flight times for Chicago to Cancun with 29.

Question : How many days should you spend in Cancun if you're flying in from Chicago?
Answer : Travelers from MDW to CUN stay seven days on average.