
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
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 15% on select hotels after you book a flight*
Cheap flights from Chicago to Cancun (MDW-CUN)
Prices were available within the past 7 days and start at €131 for one-way flights and €279 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, 8 Jan - Thu, 15 Jan
MDW
Chicago
CUN
Cancun
€279 Return, found 3 days ago
€279
Return
found 3 days ago

Thu, 8 Jan - Thu, 15 Jan
MDW
Chicago
CUN
Cancun
€281 Return, found 3 days ago
€281
Return
found 3 days ago

Thu, 22 Jan - Mon, 2 Feb
MDW
Chicago
CUN
Cancun
€287 Return, found 5 days ago
€287
Return
found 5 days ago

Thu, 8 Jan - Thu, 15 Jan
MDW
Chicago
CUN
Cancun
€288 Return, found 3 days ago
€288
Return
found 3 days ago

Thu, 22 Jan - Mon, 2 Feb
MDW
Chicago
CUN
Cancun
€330 Return, found 5 days ago
€330
Return
found 5 days ago

Thu, 22 Jan - Mon, 2 Feb
MDW
Chicago
CUN
Cancun
€335 Return, found 5 days ago
€335
Return
found 5 days ago

Thu, 8 Jan - Thu, 15 Jan
MDW
Chicago
CUN
Cancun
€335 Return, found 3 days ago
€335
Return
found 3 days ago

Thu, 8 Jan - Thu, 15 Jan
MDW
Chicago
CUN
Cancun
€337 Return, found 3 days ago
€337
Return
found 3 days ago

Wed, 31 Dec - Thu, 8 Jan
MDW
Chicago
CUN
Cancun
€338 Return, found 1 day ago
€338
Return
found 1 day ago

Mon, 4 May - Sun, 10 May
MDW
Chicago
CUN
Cancun
€426 Return, found 2 days ago
€426
Return
found 2 days ago
Find the cheapest month to fly from Chicago (MDW) to Cancun (CUN)
July is typically the cheapest month to fly
From €212 - €563 per traveller.
Origin airport | Midway Intl. |
|---|---|
Destination airport | Cancun Intl. |
Return price | €279 |
Distance | 2294 km |
Average flight time | 4 hours 45 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 €131 and roundtrip prices from €279. 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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*Available to Expedia members.