$137 Cheap Flights from Cancun (CUN) to Chicago (MDW)

View $137 flight on Tue, Jun 10, 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.

Cheap Flights from Cancun to Chicago (CUN-MDW)

Prices were available within the past 7 days and start at $137 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Jul 31 - Sun, Aug 3
CUN
Cancun
MDW
Chicago
$249 Roundtrip, found 5 hours ago
$249
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Cancun to Chicago, returning Sun, Aug 3, priced at $249 found 5 hours ago
Southwest Airlines
Wed, Jul 16 - Sat, Jul 19
CUN
Cancun
MDW
Chicago
$259 Roundtrip, found 16 hours ago
$259
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Wed, Jul 16 from Cancun to Chicago, returning Sat, Jul 19, priced at $259 found 16 hours ago
Southwest Airlines
Sat, Jul 19 - Fri, Jul 25
CUN
Cancun
MDW
Chicago
$270 Roundtrip, found 2 days ago
$270
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Jul 19 from Cancun to Chicago, returning Fri, Jul 25, priced at $270 found 2 days ago
Southwest Airlines
Thu, May 1 - Thu, May 8
CUN
Cancun
MDW
Chicago
$282 Roundtrip, found 15 hours ago
$282
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Thu, May 1 from Cancun to Chicago, returning Thu, May 8, priced at $282 found 15 hours ago
Delta
Thu, Jul 10 - Mon, Jul 14
CUN
Cancun
MDW
Chicago
$289 Roundtrip, found 4 hours ago
$289
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Jul 10 from Cancun to Chicago, returning Mon, Jul 14, priced at $289 found 4 hours ago
Southwest Airlines
Thu, Jul 31 - Sun, Aug 3
CUN
Cancun
MDW
Chicago
$290 Roundtrip, found 5 hours ago
$290
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Cancun to Chicago, returning Sun, Aug 3, priced at $290 found 5 hours ago
Southwest Airlines
Sat, Jul 19 - Fri, Jul 25
CUN
Cancun
MDW
Chicago
$292 Roundtrip, found 2 days ago
$292
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Jul 19 from Cancun to Chicago, returning Fri, Jul 25, priced at $292 found 2 days ago
Aeromexico
Wed, Jun 11 - Sat, Jun 14
CUN
Cancun
MDW
Chicago
$299 Roundtrip, found 3 days ago
$299
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Wed, Jun 11 from Cancun to Chicago, returning Sat, Jun 14, priced at $299 found 3 days ago
Frontier Airlines
Fri, Jul 11 - Sat, Jul 19
CUN
Cancun
MDW
Chicago
$335 Roundtrip, just found
$335
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 11 from Cancun to Chicago, returning Sat, Jul 19, priced at $335 just found
Volaris
Sun, Feb 8 - Thu, Feb 12
CUN
Cancun
MDW
Chicago
$527 Roundtrip, found 5 hours ago
$527
Roundtrip
found 5 hours ago
Select Volaris flight, departing Sun, Feb 8 from Cancun to Chicago, returning Thu, Feb 12, priced at $527 found 5 hours ago

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 flight leaving CUN on May 15 2025 and touching down at MDW. The price was last updated on April 22 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 $137. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from CUN on July 17 2025. Prices were last updated on April 22 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.
*Available to One Key members.