₹12,307 Cheap Flights from Chicago (MDW) to Cancun (CUN)

View ₹12,307 flight on Mon, 18 Aug 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at ₹12,307 for one-way flights and ₹33,600 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, 17 Aug - Wed, 20 Aug
MDW
Chicago
CUN
Cancun
₹33,600 Return, found 5 days ago
₹33,600
Return
found 5 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Cancun, returning Wed, 20 Aug, priced at ₹33,600 found 5 days ago
Delta
Mon, 1 Dec - Mon, 15 Dec
MDW
Chicago
CUN
Cancun
₹33,979 Return, found 4 days ago
₹33,979
Return
found 4 days ago
Select Delta flight, departing Mon, 1 Dec from Chicago to Cancun, returning Mon, 15 Dec, priced at ₹33,979 found 4 days ago
Delta
Sun, 17 Aug - Wed, 20 Aug
MDW
Chicago
CUN
Cancun
₹34,460 Return, found 5 days ago
₹34,460
Return
found 5 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Cancun, returning Wed, 20 Aug, priced at ₹34,460 found 5 days ago
Delta
Sun, 17 Aug - Wed, 20 Aug
MDW
Chicago
CUN
Cancun
₹38,240 Return, found 5 days ago
₹38,240
Return
found 5 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Cancun, returning Wed, 20 Aug, priced at ₹38,240 found 5 days ago
Delta
Sun, 17 Aug - Wed, 20 Aug
MDW
Chicago
CUN
Cancun
₹39,100 Return, found 5 days ago
₹39,100
Return
found 5 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Cancun, returning Wed, 20 Aug, priced at ₹39,100 found 5 days ago
Delta
Sun, 17 Aug - Wed, 20 Aug
MDW
Chicago
CUN
Cancun
₹46,835 Return, found 5 days ago
₹46,835
Return
found 5 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Cancun, returning Wed, 20 Aug, priced at ₹46,835 found 5 days ago
Delta
Sun, 17 Aug - Wed, 20 Aug
MDW
Chicago
CUN
Cancun
₹47,695 Return, found 5 days ago
₹47,695
Return
found 5 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Cancun, returning Wed, 20 Aug, priced at ₹47,695 found 5 days ago
Delta
Sun, 17 Aug - Wed, 20 Aug
MDW
Chicago
CUN
Cancun
₹50,785 Return, found 5 days ago
₹50,785
Return
found 5 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Cancun, returning Wed, 20 Aug, priced at ₹50,785 found 5 days ago
Delta
Mon, 1 Dec - Mon, 15 Dec
MDW
Chicago
CUN
Cancun
₹51,179 Return, found 4 days ago
₹51,179
Return
found 4 days ago
Select Delta flight, departing Mon, 1 Dec from Chicago to Cancun, returning Mon, 15 Dec, priced at ₹51,179 found 4 days ago
Delta
Mon, 1 Dec - Mon, 15 Dec
MDW
Chicago
CUN
Cancun
₹52,899 Return, found 4 days ago
₹52,899
Return
found 4 days ago
Select Delta flight, departing Mon, 1 Dec from Chicago to Cancun, returning Mon, 15 Dec, priced at ₹52,899 found 4 days ago

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

July is typically the cheapest month to fly

From ₹21,070 - ₹49,731 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to Cancun route information
Origin airport
Midway Intl.
Destination airport
Cancun Intl.
Return price
₹33,600
Distance
2294 km
Average flight time
3 hours 37 mins

Chicago to Cancun Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Cancun will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Cancun.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with MDW to CUN flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to CUN with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
The lowest price advertised for a round-trip flight between Midway Airport and CUN is ₹33,600. But you better act soon. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to Cancun Intl. Airport (CUN)?
Most flights can be cancelled online, but each airline has its own set of terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Airport to Cancun Intl. Airport (CUN) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Chicago Airport to Cancun Intl. Airport (CUN) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Midway Airport to CUN?
The flight distance from Chicago Airport to Cancun Intl. Airport (CUN) is 2,300 kilometres. Listen to your favourite tunes or get stuck into a book and the trip will fly by.
Which airlines fly direct from Chicago Airport to Cancun Airport?
Southwest Airlines (WN) will fly you from Chicago Airport to Cancun Intl. Airport (CUN) comfortably and reliably. Choose from 34 direct flights each month on this route.
Are Midway Airport to Cancun Intl. Airport (CUN) flight tickets cheaper when they're purchased at the last minute?
It is possible to score a great last-minute deal from Midway Airport to Cancun Airport, but there's no guarantee. As many airlines release prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can feel confident knowing you're always seeing the latest offers.

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to Cancun
₹29,650.00
*Available to Expedia members.