
Popular airlines from Chicago Midway Airport (MDW) to Cancun Intl. Airport (CUN)
- Southwest Airlines
Southwest Airlines
- Delta
Delta
- Aeromexico
Aeromexico
- Frontier Airlines
Frontier Airlines
- Volaris
Volaris
- Plan, book, fly with confidence
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Cheap flights from Chicago to Cancun (MDW-CUN)
Prices were available within the past 7 days and start at €127 for one-way flights and €277 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, 6 Sep - Sat, 13 Sep
MDW
Chicago
CUN
Cancun
€277 Return, found 1 day ago
€277
Return
found 1 day ago

Sat, 6 Sep - Sat, 13 Sep
MDW
Chicago
CUN
Cancun
€277 Return, found 1 day ago
€277
Return
found 1 day ago

Sat, 6 Sep - Sat, 13 Sep
MDW
Chicago
CUN
Cancun
€277 Return, found 1 day ago
€277
Return
found 1 day ago

Sat, 6 Sep - Sat, 13 Sep
MDW
Chicago
CUN
Cancun
€280 Return, found 1 day ago
€280
Return
found 1 day ago

Sat, 6 Sep - Sat, 13 Sep
MDW
Chicago
CUN
Cancun
€285 Return, found 1 day ago
€285
Return
found 1 day ago

Sat, 6 Sep - Sat, 13 Sep
MDW
Chicago
CUN
Cancun
€303 Return, found 1 day ago
€303
Return
found 1 day ago

Fri, 5 Sep - Tue, 9 Sep
MDW
Chicago
CUN
Cancun
€307 Return, found 1 day ago
€307
Return
found 1 day ago

Fri, 5 Sep - Tue, 9 Sep
MDW
Chicago
CUN
Cancun
€312 Return, found 1 day ago
€312
Return
found 1 day ago

Sat, 6 Sep - Sat, 13 Sep
MDW
Chicago
CUN
Cancun
€330 Return, found 1 day ago
€330
Return
found 1 day ago

Mon, 19 Jan - Mon, 26 Jan
MDW
Chicago
CUN
Cancun
€555 Return, found 8 hours ago
€555
Return
found 8 hours ago
Find the cheapest month to fly from Chicago (MDW) to Cancun (CUN)
July is typically the cheapest month to fly
From €213 - €348 per traveller.
Graph displaying average flight prices per month
Origin airport | Midway Intl. |
Destination airport | Cancun Intl. |
Airlines serving | Aeromexico, Delta, Volaris |
Return price | €277 |
Distance | 2294 km |
Average flight time | 2 hours 35 mins |
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 €127 and roundtrip prices from €277. 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 to travel arrangements today and embark on the journey of a lifetime in Cancun.
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Top Routes from Chicago
Top Routes to Cancun
- Newark Liberty Intl. Airport to Cancun (EWR - CUN)
- Brussels to Cancun (BRU - CUN)
- Paris to Cancun (CDG - CUN)
- New York to Cancun (JFK - CUN)
- Dublin to Cancun (DUB - CUN)
- Madrid to Cancun (MAD - CUN)
- Vienna to Cancun (VIE - CUN)
- Frankfurt to Cancun (FRA - CUN)
- Lisbon to Cancun (LIS - CUN)
- London to Cancun (LHR - CUN)
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*Available to Expedia members.