S$197 Cheap Flights from Chicago to Cancun

View S$197 flight on Fri, 23 Jan, 2026Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    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$197 for one-way flights and S$420 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$420 Return, found 15 hours ago
S$420
Return
found 15 hours ago
Select Delta flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$420 found 15 hours ago
Delta
Wed, 18 Mar - Tue, 24 Mar
ORD
Chicago
CUN
Cancun
S$421 Return, found 5 days ago
S$421
Return
found 5 days ago
Select Delta flight, departing Wed, 18 Mar from Chicago to Cancun, returning Tue, 24 Mar, priced at S$421 found 5 days ago
Delta
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$433 Return, found 15 hours ago
S$433
Return
found 15 hours ago
Select Delta flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$433 found 15 hours ago
Delta
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$446 Return, found 15 hours ago
S$446
Return
found 15 hours ago
Select Delta flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$446 found 15 hours ago
United
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$470 Return, found 15 hours ago
S$470
Return
found 15 hours ago
Select United flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$470 found 15 hours ago
Delta
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$471 Return, found 15 hours ago
S$471
Return
found 15 hours ago
Select Delta flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$471 found 15 hours ago
American Airlines
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$476 Return, found 15 hours ago
S$476
Return
found 15 hours ago
Select American Airlines flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$476 found 15 hours ago
United
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$477 Return, found 15 hours ago
S$477
Return
found 15 hours ago
Select United flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$477 found 15 hours ago
Aeromexico
Sun, 1 Feb - Sat, 7 Feb
ORD
Chicago
CUN
Cancun
S$502 Return, found 15 hours ago
S$502
Return
found 15 hours ago
Select Aeromexico flight, departing Sun, 1 Feb from Chicago to Cancun, returning Sat, 7 Feb, priced at S$502 found 15 hours ago
Arajet
Wed, 4 Feb - Sun, 8 Feb
ORD
Chicago
CUN
Cancun
S$548 Return, found 1 day ago
S$548
Return
found 1 day ago
Select Arajet flight, departing Wed, 4 Feb from Chicago to Cancun, returning Sun, 8 Feb, priced at S$548 found 1 day ago

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

January is typically the cheapest month to fly

From S$239 - S$455 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$420. 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.
Airlines serving
Aeromexico, Air Canada, American Airlines, Arajet, Copa, Delta, United, avianca
Return price
S$420
Distance
2316 km
Average flight time
4 hours 56 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

*Available to Expedia members.