S$271 Cheap Flights from Chicago to Cancun

View S$271 flight on Fri, 5 Dec, 2025Opens in a new window

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

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Cheap Flights from Chicago to Cancun (MDW-CUN)

Prices were available within the past 7 days and start at S$271 for one-way flights and S$410 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$410 Return, found 6 days ago
S$410
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$410 found 6 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$429 Return, found 6 days ago
S$429
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$429 found 6 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$591 Return, found 6 days ago
S$591
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$591 found 6 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$668 Return, found 6 days ago
S$668
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$668 found 6 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$687 Return, found 6 days ago
S$687
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$687 found 6 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$787 Return, found 5 days ago
S$787
Return
found 5 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$787 found 5 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$829 Return, found 6 days ago
S$829
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$829 found 6 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$1,116 Return, found 6 days ago
S$1,116
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$1,116 found 6 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
MDW
Chicago
CUN
Cancun
S$1,135 Return, found 6 days ago
S$1,135
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$1,135 found 6 days ago

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

July is typically the cheapest month to fly

From S$317 - S$1,066 per traveller.
Chicago to Cancun route information
Origin airport
Midway Intl.
Destination airport
Cancun Intl.
Return price
S$410
Distance
2294 km
Average flight time
3 hours 37 mins

Perfect flights from Chicago to Cancun

Your Journey from Chicago to Cancun

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Cancun caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Midway Intl. to Cancun Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 11 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Cancun Flights

Experience the joy of finding cheap flights from Midway Intl. to Cancun Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$271 and roundtrip prices from S$410*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Cancun with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Cancun

Picture yourself stepping off the plane in Cancun and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Cancun Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Cancun.
 

Beyond the Flight – Exploring Cancun

With Expedia, your adventure extends beyond the flight. Explore Cancun at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Cancun with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Cancun with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

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 S$410. 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.

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to Cancun
S$459.90
*Available to Expedia members.