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Cheap Flights from Chicago to Cancun $245.16

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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 : In the next four weeks, what day should you book your trip?
Answer : January 25th offers bookings (as of January 16th) that are 24% below the average price for this route. Saving on booking fees means you'll have more cash in your pocket for the trip.

Question : Can you cut down on flight costs by changing the day of the week you travel to Cancun?
Answer : The best day to fly on a budget this month is Monday. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.

Question : How long does it take to get from MDW to CUN?
Answer : Southwest Airlines can get you there in 3 hours and 40 minutes. So, if you were to leave Chicago at 8:10 AM, you would arrive in Cancun at 12:50 PM EST (remember, there is a one-hour time difference).

Question : How many days should you spend in Cancun if you're flying in from Chicago?
Answer : Over the next two months, travelers from MDW to CUN are planning on staying for seven days on average.