¥41,050 Cheap Flights from Cancun (CUN) to Chicago (MDW)

Bundle Your Flight + Hotel & Save!

Featured airlines

    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

Cheap Flights from Cancun to Chicago (CUN-MDW)

Prices were available within the past 7 days and start at ¥41,050 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flights from Cancun (CUN) to Chicago (MDW)
Origin airport
Cancun Intl.
Destination airport
Midway Intl.
Distance
2294 km

Cancun to Chicago 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 Cancun to 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 Chicago.

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 CUN to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Cancun 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 MDW 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.

Frequently asked questions

How much is a flight from Cancun Airport to Midway Airport?
If you’re planning on traveling between Cancun Intl. Airport (CUN) and Midway Airport, round-trip journeys start from . This price is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don’t let a good deal slip through your fingers. Book today and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Cancun Airport to Midway Airport?
We understand that things come up unexpectedly, so we’ve made it as hassle-free as possible for you to cancel your flight online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from CUN to Chicago Airport 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 Cancun Airport to Chicago Airport flights, you’ll see a “no change fees” filter for you to select.
How many hours is the flight from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
The flight time from CUN to Chicago Airport is approximately 5 hours and 47 minutes. Put your headphones on, listen to a good podcast and your time in the air will whiz by.
How far is the flight from Cancun Airport to Midway Intl. Airport (MDW)?
The flight distance from Cancun to Chicago is 2,300 kilometers. Pack yourself a drink, a snack and a good movie. Keep yourself occupied and the hours will fly by.
Which airlines fly direct from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
Unfortunately, there are no airlines that directly fly between Cancun Intl. Airport (CUN) and Midway Intl. Airport (MDW). You’ll need to book a flight with at least one stop.
Are Cancun Airport to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can occasionally pick up a bargain, with some super cheap fares from Cancun Intl. Airport (CUN) to MDW showing up a few weeks before the date of departure. If you’d rather plan ahead, Expedia compares and updates the best flight deals continuously — as early as a year in advance in some cases. It depends on the carrier though, as not every airline advertises prices that far in advance.
Chicago nearby Airports

Chicago

*Available to Expedia members.