A coastal cityscape with a beach, clear turquoise waters, and high-rise hotels.

₹21,552 Cheap Flights from Chicago (MDW) to Cancun (CUN)

Flight 1

Cheap Flights from Chicago to Cancun (MDW-CUN)

Prices were available within the past 7 days and start at ₹21,552 for one-way flights and ₹45,758 for return, for the period specified. Prices and availability are subject to change.
Delta
Sat, 30 Jan - Wed, 3 Feb
MDW
Chicago
CUN
Cancun
₹45,758
Return
Found 6 days ago
Select Delta flight, departing Sat, 30 Jan from Chicago to Cancun, returning Wed, 3 Feb, priced at ₹45,758 Found 6 days ago
Delta
Sun, 15 Nov - Thu, 19 Nov
MDW
Chicago
CUN
Cancun
₹47,611
Return
Found 6 days ago
Select Delta flight, departing Sun, 15 Nov from Chicago to Cancun, returning Thu, 19 Nov, priced at ₹47,611 Found 6 days ago
Delta
Sun, 15 Nov - Thu, 19 Nov
MDW
Chicago
CUN
Cancun
₹49,133
Return
Found 3 days ago
Select Delta flight, departing Sun, 15 Nov from Chicago to Cancun, returning Thu, 19 Nov, priced at ₹49,133 Found 3 days ago
Delta
Sat, 30 Jan - Wed, 3 Feb
MDW
Chicago
CUN
Cancun
₹50,898
Return
Found 6 days ago
Select Delta flight, departing Sat, 30 Jan from Chicago to Cancun, returning Wed, 3 Feb, priced at ₹50,898 Found 6 days ago
Delta
Sun, 15 Nov - Thu, 19 Nov
MDW
Chicago
CUN
Cancun
₹52,176
Return
Found 6 days ago
Select Delta flight, departing Sun, 15 Nov from Chicago to Cancun, returning Thu, 19 Nov, priced at ₹52,176 Found 6 days ago
Delta
Sat, 30 Jan - Sat, 6 Feb
MDW
Chicago
CUN
Cancun
₹56,513
Return
Found 6 days ago
Select Delta flight, departing Sat, 30 Jan from Chicago to Cancun, returning Sat, 6 Feb, priced at ₹56,513 Found 6 days ago
Delta
Sun, 15 Nov - Thu, 19 Nov
MDW
Chicago
CUN
Cancun
₹57,311
Return
Found 6 days ago
Select Delta flight, departing Sun, 15 Nov from Chicago to Cancun, returning Thu, 19 Nov, priced at ₹57,311 Found 6 days ago
Delta
Sun, 15 Nov - Thu, 19 Nov
MDW
Chicago
CUN
Cancun
₹58,848
Return
Found 3 days ago
Select Delta flight, departing Sun, 15 Nov from Chicago to Cancun, returning Thu, 19 Nov, priced at ₹58,848 Found 3 days ago
Delta
Sat, 30 Jan - Sat, 6 Feb
MDW
Chicago
CUN
Cancun
₹61,653
Return
Found 6 days ago
Select Delta flight, departing Sat, 30 Jan from Chicago to Cancun, returning Sat, 6 Feb, priced at ₹61,653 Found 6 days ago
Delta
Sat, 30 Jan - Sat, 6 Feb
MDW
Chicago
CUN
Cancun
₹67,273
Return
Found 6 days ago
Select Delta flight, departing Sat, 30 Jan from Chicago to Cancun, returning Sat, 6 Feb, priced at ₹67,273 Found 6 days ago

Alternative airports near Cancun

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Cozumel Intl. CZM. Average driving time to city centre is 5 hours 15 minutes.
CZM
Cozumel Intl.
Average driving time to city centre5 h 15 min
Search flights

Book with confidence

Perfect flights from Chicago to Cancun

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Cancun. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
Our flexible Midway Intl. to Cancun Intl. ticket options cater to your travel preferences, with incredible one-way fares from ₹21,552 and roundtrip prices ₹45,758. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Cancun Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your MDW to CUN travel arrangements today and embark on the journey of a lifetime in Cancun.

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 ₹45,758. 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 cancelled 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 kilometres. Listen to your favourite 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

Origin airport
Chicago Midway Airport
Destination airport
Cancun Intl. Airport
Distance
2,308 km away
Airlines serving
Southwest Airlines, Delta, Frontier Airlines, Aeromexico
Popular airline
Southwest Airlines
Return price
₹45,758
Average flight time
3 hours 45 mins
*Available to Expedia members.