$135 Cheap Flights from Chicago (MDW) to Cancun (CUN)

View $135 flight on Sun, Nov 16, 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 $135 for one-way flights and $271 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Dec 15 - Sat, Dec 20
MDW
Chicago
CUN
Cancun
$271 Roundtrip, found 8 hours ago
$271
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Mon, Dec 15 from Chicago to Cancun, returning Sat, Dec 20, priced at $271 found 8 hours ago
Southwest Airlines
Mon, Sep 8 - Sat, Sep 13
MDW
Chicago
CUN
Cancun
$276 Roundtrip, found 11 hours ago
$276
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Sep 8 from Chicago to Cancun, returning Sat, Sep 13, priced at $276 found 11 hours ago
Southwest Airlines
Sat, Sep 27 - Sat, Oct 4
MDW
Chicago
CUN
Cancun
$281 Roundtrip, found 12 hours ago
$281
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sat, Sep 27 from Chicago to Cancun, returning Sat, Oct 4, priced at $281 found 12 hours ago
Southwest Airlines
Sat, Sep 6 - Sat, Sep 20
MDW
Chicago
CUN
Cancun
$286 Roundtrip, found 13 hours ago
$286
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Chicago to Cancun, returning Sat, Sep 20, priced at $286 found 13 hours ago
Southwest Airlines
Fri, Dec 12 - Thu, Dec 18
MDW
Chicago
CUN
Cancun
$291 Roundtrip, just found
$291
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Dec 12 from Chicago to Cancun, returning Thu, Dec 18, priced at $291 just found
Southwest Airlines
Sat, Sep 27 - Sat, Oct 4
MDW
Chicago
CUN
Cancun
$296 Roundtrip, found 12 hours ago
$296
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sat, Sep 27 from Chicago to Cancun, returning Sat, Oct 4, priced at $296 found 12 hours ago
Aeromexico
Sun, Nov 16 - Sat, Nov 22
MDW
Chicago
CUN
Cancun
$297 Roundtrip, found 12 hours ago
$297
Roundtrip
found 12 hours ago
Select Aeromexico flight, departing Sun, Nov 16 from Chicago to Cancun, returning Sat, Nov 22, priced at $297 found 12 hours ago
Delta
Sun, Nov 16 - Thu, Nov 20
MDW
Chicago
CUN
Cancun
$308 Roundtrip, just found
$308
Roundtrip
just found
Select Delta flight, departing Sun, Nov 16 from Chicago to Cancun, returning Thu, Nov 20, priced at $308 just found
Frontier Airlines
Sat, Oct 25 - Fri, Oct 31
MDW
Chicago
CUN
Cancun
$329 Roundtrip, found 13 hours ago
$329
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Chicago to Cancun, returning Fri, Oct 31, priced at $329 found 13 hours ago
Volaris
Sun, Feb 1 - Fri, Feb 6
MDW
Chicago
CUN
Cancun
$371 Roundtrip, found 8 hours ago
$371
Roundtrip
found 8 hours ago
Select Volaris flight, departing Sun, Feb 1 from Chicago to Cancun, returning Fri, Feb 6, priced at $371 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 $246 - $664 per traveler.

Graph displaying average flight prices per month

Alternative airports near Cancun

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

Select flight to Cancun Intl. CUN. Cheapest and Closest option available. Average driving time to city center is 18 minutes. Flights from $406
CUN
Cancun Intl.
CheapestClosest
Average driving time to city center18 min
Flights from $406
Flights from Chicago (MDW) to Cancun (CUN)
Origin airport
Midway Intl.
Destination airport
Cancun Intl.
Airlines serving
Aeromexico, Delta, Frontier Airlines, Southwest Airlines, Volaris
Roundtrip price
$271
Distance
1434 mi
Average flight time
3 hours 35 mins

Chicago to Cancun Flights

The cheapest times to fly from Chicago to Cancun

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Cancun are during the month of December. You can find some of the cheapest flights from Chicago to Cancun with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Cancun

Sunday is one of the best days to book for cheap flights from Chicago to Cancun: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Cancun

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Cancun in 2025. You can also book with separate airlines for your outbound and return journeys, from $135 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Cancun flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Cancun airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN) cost?
Grab a cheap one-way flight from $135 or cheap return flight from $271 from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
December is the cheapest month to fly from MDW to CUN. Avoiding peak travel times is often the key to finding better deals on flights.
Which airlines fly direct from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
When setting off from Midway Intl. Airport (MDW), you can hop on a nonstop flight to Cancun Intl. Airport (CUN) with Southwest Airlines.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to CUN flight.
How many flights per day from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
On average, Midway Intl. Airport (MDW) only has 1 nonstop flight to Cancun Intl. Airport (CUN) daily. To explore more options, try Expedia's easy-to-use filters. Simply enter your dates, then choose "1 Stop" or "2+ Stops" to find flights with layovers.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
More people fly between MDW and CUN at 9 AM than at any other point in the day. Rather go when it's quieter? Travel outside of rush hours and there's a chance you'll save on your fare as well.
What day of the week has the most flights from MDW to CUN?
Jet off on a Friday if you're searching for the largest selection of flights from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN).
What is the earliest flight from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
Midway Intl. Airport (MDW)'s earliest flight to Cancun Intl. Airport (CUN) departs at approximately 7:55AM UTC-6. With a total journey time of 3h 50m, you'll touch down at around 12:45PM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
It takes roughly 3 hours and 50 minutes to cover the 1,450 mi from MDW to CUN.
What is the best time to fly from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN) route, aim to travel before 3 PM. Later departures have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Cancun from Midway Intl. Airport (MDW)?
If you're boarding a direct flight from Midway Intl. Airport (MDW) to Cancun, Cancun Intl. Airport (CUN) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN) last-minute?
Waiting until just before your trip to book your flight from MDW to CUN often results in higher prices. While you may come across some last-minute deals, there's no guarantee. Be flexible with your itinerary to boost your chances of landing a bargain.
Is it cheaper to book a MDW to CUN flight and hotel package?
Opting for a MDW to CUN flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Select from our impressive range of accommodations and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
Typically, it's possible to cancel or reschedule your MDW to CUN flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.