S$182 Cheap Flights from Chicago to Cancun

View S$182 flight on Thu, 14 Aug, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)

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Cheap Flights from Chicago to Cancun (ORD-CUN)

Prices were available within the past 7 days and start at S$182 for one-way flights and S$432 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
CUN
Cancun
S$432 Return, found 5 hours ago
S$432
Return
found 5 hours ago
Select Delta flight, departing Thu, 14 Aug from Chicago to Cancun, returning Thu, 21 Aug, priced at S$432 found 5 hours ago
Delta
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
CUN
Cancun
S$436 Return, found 6 days ago
S$436
Return
found 6 days ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Cancun, returning Tue, 26 Aug, priced at S$436 found 6 days ago
American Airlines
Sat, 23 Aug - Fri, 29 Aug
ORD
Chicago
CUN
Cancun
S$458 Return, found 5 days ago
S$458
Return
found 5 days ago
Select American Airlines flight, departing Sat, 23 Aug from Chicago to Cancun, returning Fri, 29 Aug, priced at S$458 found 5 days ago
United
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
CUN
Cancun
S$468 Return, found 6 days ago
S$468
Return
found 6 days ago
Select United flight, departing Tue, 19 Aug from Chicago to Cancun, returning Tue, 26 Aug, priced at S$468 found 6 days ago
Delta
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
CUN
Cancun
S$477 Return, found 5 hours ago
S$477
Return
found 5 hours ago
Select Delta flight, departing Thu, 14 Aug from Chicago to Cancun, returning Thu, 21 Aug, priced at S$477 found 5 hours ago
American Airlines
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
CUN
Cancun
S$479 Return, found 5 hours ago
S$479
Return
found 5 hours ago
Select American Airlines flight, departing Thu, 14 Aug from Chicago to Cancun, returning Thu, 21 Aug, priced at S$479 found 5 hours ago
Delta
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
CUN
Cancun
S$483 Return, found 6 days ago
S$483
Return
found 6 days ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Cancun, returning Tue, 26 Aug, priced at S$483 found 6 days ago
Delta
Sat, 23 Aug - Fri, 29 Aug
ORD
Chicago
CUN
Cancun
S$483 Return, found 5 days ago
S$483
Return
found 5 days ago
Select Delta flight, departing Sat, 23 Aug from Chicago to Cancun, returning Fri, 29 Aug, priced at S$483 found 5 days ago
avianca
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
CUN
Cancun
S$594 Return, found 4 days ago
S$594
Return
found 4 days ago
Select avianca flight, departing Sun, 10 Aug from Chicago to Cancun, returning Sun, 17 Aug, priced at S$594 found 4 days ago
Aeromexico
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
CUN
Cancun
S$685 Return, found 6 days ago
S$685
Return
found 6 days ago
Select Aeromexico flight, departing Tue, 19 Aug from Chicago to Cancun, returning Tue, 26 Aug, priced at S$685 found 6 days ago

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

January is typically the cheapest month to fly

From S$236 - S$582 per traveller.

Graph displaying average flight prices per month

Chicago to Cancun route information
Origin airport
O'Hare Intl.
Destination airport
Cancun Intl.
Return price
S$431
Distance
2316 km
Average flight time
3 hours 48 mins

Flights from Chicago to Cancun

There are several airlines that operate frequent flights from Chicago (ORD) to Cancun (CUN) including

The earliest flight leaves O'Hare Intl. Airport at 06:00 and arrives at Cancun Intl. Airport at 09:45. The last flight of the day departs Chicago at 17:45 and arrives at Cancun at 22:35.

The flight distance from Chicago to Cancun is about 2343 km, the shortest flight is 03 hours 30 minutes with Virgin Atlantic.

Expedia lets you search across the largest number of airlines and Cancun flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago Cancun flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to Cancun trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Cancun flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to Cancun with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from O'Hare Airport to Cancun Intl. Airport (CUN)?
If you're travelling between O'Hare Intl. Airport (ORD) and Cancun Intl. Airport (CUN), round-trip journeys start from S$432. This price is based on airfares available within the last 7 days on Expedia for flights departing within the next year, so don't hang around. Book today and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Cancun Airport?
Every air carrier has its own terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from O'Hare Airport to Cancun Airport 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 ORD to CUN flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Cancun Intl. Airport (CUN)?
The flight distance between O'Hare Airport and Cancun Intl. Airport (CUN) is 2,300 kilometres. Bring a drink, a snack and an interesting book to read. Keep yourself entertained and time will zip by.
Which airlines fly direct from ORD to CUN?
Travelling from O'Hare Intl. Airport (ORD) to CUN is easy when you have a nice range of airlines to choose from. These are some of the best:

  • American Airlines - (AA) with 91 monthly flights
  • United Airlines - (UA) with 65 monthly flights
  • Frontier Airlines - (F9) with 30 monthly flights
  • Spirit Airlines - (NK) with 17 monthly flights

Are O'Hare Intl. Airport (ORD) to CUN flight tickets cheaper when they're purchased at the last minute?
Booking your trip from O'Hare Intl. Airport (ORD) to Cancun Airport last minute could be your ticket to a fantastic deal. However, you might miss out on a flight altogether! If you'd prefer not to take any chances, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back often as deals are updated all the time on Expedia.

Explore a world of travel with Expedia

Cancun Airports

Cozumel

Chicago to Cozumel Intl.
S$735.20
Chicago Airports

Chicago

Midway Intl. to Cancun
S$405.40
*Available to Expedia members.