$139 Cheap Flights from Cancun (CUN) to Chicago (MDW)

View $139 flight on Tue, Jan 13, 2026Opens in a new window

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

Cheap Flights from Cancun to Chicago (CUN-MDW)

Prices were available within the past 7 days and start at $139 for one-way flights and $255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Feb 26 - Mon, Mar 2
CUN
Cancun
MDW
Chicago
$255 Roundtrip, just found
$255
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Feb 26 from Cancun to Chicago, returning Mon, Mar 2, priced at $255 just found
Southwest Airlines
Sat, Nov 15 - Mon, Nov 17
CUN
Cancun
MDW
Chicago
$260 Roundtrip, found 19 hours ago
$260
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Cancun to Chicago, returning Mon, Nov 17, priced at $260 found 19 hours ago
Southwest Airlines
Sat, Feb 14 - Tue, Feb 17
CUN
Cancun
MDW
Chicago
$265 Roundtrip, found 2 hours ago
$265
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Cancun to Chicago, returning Tue, Feb 17, priced at $265 found 2 hours ago
Southwest Airlines
Mon, Nov 24 - Sat, Nov 29
CUN
Cancun
MDW
Chicago
$275 Roundtrip, found 1 hour ago
$275
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Mon, Nov 24 from Cancun to Chicago, returning Sat, Nov 29, priced at $275 found 1 hour ago
Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
CUN
Cancun
MDW
Chicago
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Cancun to Chicago, returning Sat, Nov 1, priced at $280 found 1 day ago
Southwest Airlines
Sat, Nov 1 - Sat, Nov 8
CUN
Cancun
MDW
Chicago
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Cancun to Chicago, returning Sat, Nov 8, priced at $280 found 2 days ago
Delta
Wed, Feb 11 - Tue, Feb 17
CUN
Cancun
MDW
Chicago
$295 Roundtrip, found 12 hours ago
$295
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Feb 11 from Cancun to Chicago, returning Tue, Feb 17, priced at $295 found 12 hours ago
Aeromexico
Fri, Oct 31 - Fri, Nov 7
CUN
Cancun
MDW
Chicago
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Fri, Oct 31 from Cancun to Chicago, returning Fri, Nov 7, priced at $302 found 1 day ago
Frontier Airlines
Thu, Jan 22 - Mon, Jan 26
CUN
Cancun
MDW
Chicago
$415 Roundtrip, found 11 hours ago
$415
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Cancun to Chicago, returning Mon, Jan 26, priced at $415 found 11 hours ago
Volaris
Mon, Feb 16 - Fri, Feb 27
CUN
Cancun
MDW
Chicago
$528 Roundtrip, found 4 days ago
$528
Roundtrip
found 4 days ago
Select Volaris flight, departing Mon, Feb 16 from Cancun to Chicago, returning Fri, Feb 27, priced at $528 found 4 days ago

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

July is typically the cheapest month to fly

From $260 - $669 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $314
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $314
Flights from Cancun (CUN) to Chicago (MDW)
Origin airport
Cancun Intl.
Destination airport
Midway Intl.
Airlines serving
Aeromexico, Delta, Frontier Airlines, Southwest Airlines, Volaris
Roundtrip price
$254
Distance
1434 mi
Average flight time
3 hours 35 mins

Cancun to Chicago Flights

The cheapest times to fly from Cancun to Chicago

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 Cancun to Chicago are during the month of February. You can find some of the cheapest flights from Cancun to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Cancun to Chicago

Sunday is one of the best days to book for cheap flights from Cancun to Chicago: 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 Cancun to Chicago

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 Cancun to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $139 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 Cancun to Chicago 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 Cancun to Chicago 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 Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $139 or cheap return flight from $255 from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
February is the cheapest month to fly from CUN to MDW. Traveling outside of peak seasons is often the key to scoring lower fares.
Which airlines fly direct from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
Board a direct flight with Southwest Airlines and travel straight from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from CUN to MDW, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
On average, just 1 direct flight departs each day from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW). Need other options? Use Expedia's filters to find flights with layovers and squeeze another destination into your itinerary.
What are the most popular departure times for flights from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
Flights between CUN and MDW are their busiest at 3 PM. If you're after a more relaxed atmosphere and potentially cheaper tickets, choose a time when demand is lower.
What day of the week has the most flights from CUN to MDW?
If you fly on a Friday, you'll get the biggest range of choices for flights from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW).
What is the earliest flight from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
The earliest flight leaving from Cancun Intl. Airport (CUN) is at around 10:50AM UTC-5. Board this flight and you'll land at Midway Intl. Airport (MDW) at approximately 1:45PM UTC-6. The total flight duration is 3h 55m.
How long does it take to fly from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
Flights from CUN to MDW have an average travel time of 3 hours and 50 minutes. The total distance between these two airports is 1,450 mi.
What is the best time to fly from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**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 Chicago from Cancun Intl. Airport (CUN)?
You can arrive at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Cancun Intl. Airport (CUN).
Is it cheaper to buy a plane ticket from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from CUN to MDW just before your journey is typically more expensive. However, if there's some wiggle room with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book a CUN to MDW flight and hotel package?
You can save money by booking a CUN to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. Once you've chosen your ideal flights and accommodations, consider other add-ons like car rentals, tours and activities.
Can I cancel or change the date of my flight from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
If you reserved your CUN to MDW flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

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*Available to One Key members.