S$194 Cheap Flights from Chicago to Cancun

View S$194 flight on Mon, 8 Dec, 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$194 for one-way flights and S$460 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$460 Return, found 5 days ago
S$460
Return
found 5 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$460 found 5 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$469 Return, found 5 days ago
S$469
Return
found 5 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$469 found 5 days ago
American Airlines
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$480 Return, found 5 days ago
S$480
Return
found 5 days ago
Select American Airlines flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$480 found 5 days ago
American Airlines
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$489 Return, found 5 days ago
S$489
Return
found 5 days ago
Select American Airlines flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$489 found 5 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$508 Return, found 5 days ago
S$508
Return
found 5 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$508 found 5 days ago
Air Canada
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$518 Return, found 5 days ago
S$518
Return
found 5 days ago
Select Air Canada flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$518 found 5 days ago
American Airlines
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$527 Return, found 5 days ago
S$527
Return
found 5 days ago
Select American Airlines flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$527 found 5 days ago
American Airlines
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$528 Return, found 5 days ago
S$528
Return
found 5 days ago
Select American Airlines flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$528 found 5 days ago
United
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$551 Return, found 5 days ago
S$551
Return
found 5 days ago
Select United flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$551 found 5 days ago
Aeromexico
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$1,404 Return, found 5 days ago
S$1,404
Return
found 5 days ago
Select Aeromexico flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$1,404 found 5 days ago

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

January is typically the cheapest month to fly

From S$238 - S$453 per traveller.

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$460. 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.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Cancun Intl.
Return price
S$460
Distance
2316 km
Average flight time
3 hours 44 mins

Book with confidence

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!

Flights from Chicago to Cancun

Explore a world of travel with Expedia

Chicago Airports

Chicago

Midway Intl. to Cancun
S$409.80
*Available to Expedia members.