AED720 Cheap Flights from Chicago (MDW) to Cancun (CUN)

View AED720 flight on Sat, 25 April 2026Opens 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 AED720 for one-way flights and AED1,050 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED1,050 Roundtrip, found 1 day ago
AED1,050
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED1,050 found 1 day ago
Frontier Airlines
Friday, 24 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED1,290 Roundtrip, found 1 day ago
AED1,290
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Friday, 24 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED1,290 found 1 day ago
Delta
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED1,500 Roundtrip, found 1 day ago
AED1,500
Roundtrip
found 1 day ago
Select Delta flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED1,500 found 1 day ago
Aeromexico
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED1,650 Roundtrip, found 1 day ago
AED1,650
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED1,650 found 1 day ago
Delta
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED1,670 Roundtrip, found 1 day ago
AED1,670
Roundtrip
found 1 day ago
Select Delta flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED1,670 found 1 day ago
Aeromexico
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED1,810 Roundtrip, found 1 day ago
AED1,810
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED1,810 found 1 day ago
Delta
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED1,940 Roundtrip, found 1 day ago
AED1,940
Roundtrip
found 1 day ago
Select Delta flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED1,940 found 1 day ago
Aeromexico
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED2,090 Roundtrip, found 1 day ago
AED2,090
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED2,090 found 1 day ago
Delta
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED2,110 Roundtrip, found 1 day ago
AED2,110
Roundtrip
found 1 day ago
Select Delta flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED2,110 found 1 day ago
Delta
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED2,170 Roundtrip, found 1 day ago
AED2,170
Roundtrip
found 1 day ago
Select Delta flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED2,170 found 1 day ago
Aeromexico
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED2,250 Roundtrip, found 1 day ago
AED2,250
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED2,250 found 1 day ago
Aeromexico
Saturday, 25 April, 2026 - Saturday, 2 May, 2026
MDW
Chicago
CUN
Cancun
AED2,310 Roundtrip, found 1 day ago
AED2,310
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Saturday, 25 April, 2026 from Chicago to Cancun, returning Saturday, 2 May, 2026, priced at AED2,310 found 1 day ago

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 AED 1,050
CUN
Cancun Intl.
CheapestClosest
Average driving time to city center18 min
Flights from AED 1,050

Frequently asked questions

Is it cheaper to buy a plane ticket from MDW to CUN last minute?
When it comes to booking your flights, being organized pays off. While it's possible to pick up a deal on a MDW to CUN flight at the last minute, prices usually don't get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days in advance. For international trips it's between three and four months.
What airports do you fly into for Cancun from Chicago?
From Chicago, you can get to Cancun via Cancun Intl. Airport (CUN), Cozumel Intl. Airport (CZM) and Isla Mujeres Airport (ISJ). Do some research into which airport works best for you before making your decision. If you settle on Cancun Intl. Airport (CUN), it's about 14 kilometers south of downtown. Use the money you save when booking your fare with Expedia to tour the city's well-known sights, such as Puerto Cancun Marina Town Center and Cancun Mall.
Can I change the date of my flight from Chicago Airport to Cancun Intl. Airport (CUN)?
It's a breeze to make changes to your Midway Intl. Airport (MDW) to Cancun Airport trip yourself. Just go to the Expedia Trips portal and select "change flight." Look around for new flights and secure the one that fits your new plans. You'll get an estimate of your flight change fee, if applicable. Alternatively, head to our Customer Service portal to connect with our Virtual Agent and quickly get answers to your questions.

Travel information

Origin airport
Midway Intl.
Destination airport
Cancun Intl.
Roundtrip price
AED1,050
Distance
2294 km
Average flight time
3 hours 32 mins

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Chicago nearby Airports

Chicago