$144 Cheap Flights from Cancun (CUN) to Chicago (MDW)

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

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Cheap Flights from Cancun to Chicago (CUN-MDW)

Prices were available within the past 7 days and start at $144 for one-way flights and $265 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Southwest Airlines
Southwest Airlines
Southwest Airlines
Southwest Airlines
Southwest Airlines
Delta
Aeromexico
Frontier Airlines
Volaris

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.

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 $144 or cheap return flight from $265 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)?
November 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.

Travel information

Travel information

Origin airport
Cancun Intl.
Destination airport
Midway Intl.
Airlines serving
Aeromexico, Delta, Frontier Airlines, Southwest Airlines, Volaris
Roundtrip price
$265
Distance
1434 mi
Average flight time
3 hours 40 mins

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