S$183 Cheap Flights from Chicago to Cancun

View S$183 flight on Sat, 16 Aug, 2025Opens in a new window

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

  • 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 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Cancun (ORD-CUN)

Prices were available within the past 7 days and start at S$183 for one-way flights and S$467 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 13 Nov - Sun, 16 Nov
ORD
Chicago
CUN
Cancun
S$467 Return, found 2 days ago
S$467
Return
found 2 days ago
Select Delta flight, departing Thu, 13 Nov from Chicago to Cancun, returning Sun, 16 Nov, priced at S$467 found 2 days ago
Delta
Sat, 16 Aug - Sat, 23 Aug
ORD
Chicago
CUN
Cancun
S$486 Return, found 3 days ago
S$486
Return
found 3 days ago
Select Delta flight, departing Sat, 16 Aug from Chicago to Cancun, returning Sat, 23 Aug, priced at S$486 found 3 days ago
Delta
Thu, 13 Nov - Sun, 16 Nov
ORD
Chicago
CUN
Cancun
S$495 Return, found 2 days ago
S$495
Return
found 2 days ago
Select Delta flight, departing Thu, 13 Nov from Chicago to Cancun, returning Sun, 16 Nov, priced at S$495 found 2 days ago
Delta
Thu, 13 Nov - Sun, 16 Nov
ORD
Chicago
CUN
Cancun
S$509 Return, found 2 days ago
S$509
Return
found 2 days ago
Select Delta flight, departing Thu, 13 Nov from Chicago to Cancun, returning Sun, 16 Nov, priced at S$509 found 2 days ago
United
Thu, 13 Nov - Sun, 16 Nov
ORD
Chicago
CUN
Cancun
S$512 Return, found 2 days ago
S$512
Return
found 2 days ago
Select United flight, departing Thu, 13 Nov from Chicago to Cancun, returning Sun, 16 Nov, priced at S$512 found 2 days ago
Delta
Sat, 16 Aug - Sat, 23 Aug
ORD
Chicago
CUN
Cancun
S$520 Return, found 3 days ago
S$520
Return
found 3 days ago
Select Delta flight, departing Sat, 16 Aug from Chicago to Cancun, returning Sat, 23 Aug, priced at S$520 found 3 days ago
Delta
Sat, 16 Aug - Sat, 23 Aug
ORD
Chicago
CUN
Cancun
S$525 Return, found 3 days ago
S$525
Return
found 3 days ago
Select Delta flight, departing Sat, 16 Aug from Chicago to Cancun, returning Sat, 23 Aug, priced at S$525 found 3 days ago
American Airlines
Thu, 13 Nov - Sun, 16 Nov
ORD
Chicago
CUN
Cancun
S$542 Return, found 2 days ago
S$542
Return
found 2 days ago
Select American Airlines flight, departing Thu, 13 Nov from Chicago to Cancun, returning Sun, 16 Nov, priced at S$542 found 2 days ago
avianca
Thu, 5 Mar - Thu, 12 Mar
ORD
Chicago
CUN
Cancun
S$575 Return, just found
S$575
Return
just found
Select avianca flight, departing Thu, 5 Mar from Chicago to Cancun, returning Thu, 12 Mar, priced at S$575 just found
Air Canada
Thu, 13 Nov - Sun, 16 Nov
ORD
Chicago
CUN
Cancun
S$653 Return, found 2 days ago
S$653
Return
found 2 days ago
Select Air Canada flight, departing Thu, 13 Nov from Chicago to Cancun, returning Sun, 16 Nov, priced at S$653 found 2 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$543 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$466
Distance
2316 km
Average flight time
3 hours 46 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$467. 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

*Available to Expedia members.