₩375,300 Cheap Flights from Chicago (MDW) to Cancun (CUN)

View ₩375,300 flight on Sun, Nov 23, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Cancun Intl. Airport (CUN)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Cancun (MDW-CUN)

Prices were available within the past 7 days and start at ₩375,300 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Chicago (MDW) to Cancun (CUN)

July is typically the cheapest month to fly

From ₩340,738 - ₩1,086,705 per traveler.

Frequently asked questions

How much is a flight from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
The lowest price advertised for a round-trip flight between Midway Airport and CUN is . But you better act soon. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to Cancun Intl. Airport (CUN)?
Most flights can be canceled online, but each airline has its own set of terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Airport to Cancun Intl. Airport (CUN) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Chicago Airport to Cancun Intl. Airport (CUN) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Midway Airport to CUN?
The flight distance from Chicago Airport to Cancun Intl. Airport (CUN) is 2,300 kilometers. Listen to your favorite tunes or get stuck into a book and the trip will fly by.
Which airlines fly direct from Chicago Airport to Cancun Airport?
Southwest Airlines (WN) will fly you from Chicago Airport to Cancun Intl. Airport (CUN) comfortably and reliably. Choose from 34 direct flights each month on this route.
Are Midway Airport to Cancun Intl. Airport (CUN) flight tickets cheaper when they're purchased at the last minute?
It is possible to score a great last-minute deal from Midway Airport to Cancun Airport, but there's no guarantee. As many airlines release prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can feel confident knowing you're always seeing the latest offers.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Cancun Intl.
Distance
2294 km
Average flight time
3 hours 35 mins

Book with confidence

Book with confidence

Chicago to Cancun Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Cancun will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Cancun.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with MDW to CUN flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to CUN with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Chicago to Cancun Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

O'Hare Intl. to Cancun
₩431,100
*Available to Expedia members.