$149 Cheap Flights from Cancun (CUN) to Chicago (MDW)

View $149 flight on Wed, Jul 16, 2025Opens in a new window

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 $149 for one-way flights and $273 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Aug 21 - Mon, Aug 25
CUN
Cancun
MDW
Chicago
$273 Roundtrip, found 18 hours ago
$273
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Thu, Aug 21 from Cancun to Chicago, returning Mon, Aug 25, priced at $273 found 18 hours ago
Southwest Airlines
Sat, Sep 20 - Sat, Sep 27
CUN
Cancun
MDW
Chicago
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Cancun to Chicago, returning Sat, Sep 27, priced at $278 found 1 day ago
Southwest Airlines
Wed, Aug 27 - Wed, Sep 3
CUN
Cancun
MDW
Chicago
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Cancun to Chicago, returning Wed, Sep 3, priced at $279 found 1 day ago
Southwest Airlines
Sat, Sep 20 - Sat, Sep 27
CUN
Cancun
MDW
Chicago
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Cancun to Chicago, returning Sat, Sep 27, priced at $288 found 1 day ago
Southwest Airlines
Fri, Sep 19 - Mon, Sep 22
CUN
Cancun
MDW
Chicago
$296 Roundtrip, found 2 days ago
$296
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Sep 19 from Cancun to Chicago, returning Mon, Sep 22, priced at $296 found 2 days ago
Delta
Fri, Sep 5 - Sun, Sep 7
CUN
Cancun
MDW
Chicago
$303 Roundtrip, found 2 days ago
$303
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 5 from Cancun to Chicago, returning Sun, Sep 7, priced at $303 found 2 days ago
Southwest Airlines
Thu, Aug 21 - Fri, Aug 22
CUN
Cancun
MDW
Chicago
$308 Roundtrip, found 3 days ago
$308
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Aug 21 from Cancun to Chicago, returning Fri, Aug 22, priced at $308 found 3 days ago
Aeromexico
Mon, Nov 3 - Fri, Nov 7
CUN
Cancun
MDW
Chicago
$329 Roundtrip, found 3 days ago
$329
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Mon, Nov 3 from Cancun to Chicago, returning Fri, Nov 7, priced at $329 found 3 days ago
Frontier Airlines
Sat, Aug 30 - Sat, Sep 6
CUN
Cancun
MDW
Chicago
$335 Roundtrip, found 5 days ago
$335
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Cancun to Chicago, returning Sat, Sep 6, priced at $335 found 5 days ago
Volaris
Thu, Oct 16 - Sat, Oct 25
CUN
Cancun
MDW
Chicago
$551 Roundtrip, found 1 day ago
$551
Roundtrip
found 1 day ago
Select Volaris flight, departing Thu, Oct 16 from Cancun to Chicago, returning Sat, Oct 25, priced at $551 found 1 day ago

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

June is typically the cheapest month to fly

From $259 - $715 per traveler.

Graph displaying average flight prices per month

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. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $248
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $248
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
$273
Distance
1434 mi
Average flight time
3 hours 40 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 August. 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 $149 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?
You can book cheap return fares starting at $249 from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving CUN on July 24 2025 and touching down at MDW. The price was last updated on July 1 2025 and has not changed since.
What is the cheapest month to fly from CUN to MDW?
The cheapest flights from CUN to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 CUN to MDW?
Book a flight from CUN to MDW with Southwest Airlines. This carrier currently offers the cheapest one-way ticket on this route, starting at $148. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from CUN on September 9 2025. Prices were last updated on July 1 2025 and have not changed since.
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.