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CUN (Cancun) to MDW (Chicago) Flights $299.4

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Cheap CUN to MDW Flights

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



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

Question : Do prices fluctuate more for this route than others?
Answer : Prices for this trip tend to fluctuate more than other flights from Mexico. They can range from $430 to $873. Prices tend to be lower the further out you book.

Question : If traveling from CUN to MDW, how long can you expect to be in the air?
Answer : Flying from CUN to MDW typically takes about three hours and 45 minutes.

Question : How many days should you spend in Chicago?
Answer : Travelers from CUN to MDW stay two weeks on average.

Question : How many departure times from Cancun International Airport (CUN) to Chicago Midway International Airport (MDW) are there on a daily basis?
Answer : The number of flight times varies by day, but on average, CUN to MDW sees only one choice. That is lower than the national average of five.

Question : Have you considered flying into O'Hare International Airport instead of Chicago Midway International Airport?
Answer : Luckily for you, there is another airport near Chicago. O'Hare International Airport (ORD) is 16 miles away, and over the next two months flights are being booked 24% cheaper than flights to Chicago Midway International Airport.

Question : Will you do what it takes to get the absolute cheapest flight?
Answer : The cheapest day to fly in August is Thursday. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : What is the shortest flight from CUN to MDW?
Answer : The shortest direct flight is three hours and 45 minutes via Southwest Airlines. If you catch the 3:00 PM EST departure, you'll arrive at 5:45 PM CDT (remember, there is a one-hour time change).