S$190 Cheap Flights from Chicago to Cancun

View S$190 flight on Mon, 29 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$190 for one-way flights and S$416 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 18 Feb - Thu, 26 Feb
ORD
Chicago
CUN
Cancun
S$416 Return, found 7 hours ago
S$416
Return
found 7 hours ago
Select Delta flight, departing Wed, 18 Feb from Chicago to Cancun, returning Thu, 26 Feb, priced at S$416 found 7 hours ago
Delta
Wed, 18 Feb - Thu, 26 Feb
ORD
Chicago
CUN
Cancun
S$416 Return, found 7 hours ago
S$416
Return
found 7 hours ago
Select Delta flight, departing Wed, 18 Feb from Chicago to Cancun, returning Thu, 26 Feb, priced at S$416 found 7 hours ago
Delta
Wed, 18 Feb - Thu, 26 Feb
ORD
Chicago
CUN
Cancun
S$420 Return, found 7 hours ago
S$420
Return
found 7 hours ago
Select Delta flight, departing Wed, 18 Feb from Chicago to Cancun, returning Thu, 26 Feb, priced at S$420 found 7 hours ago
Delta
Mon, 19 Jan - Fri, 23 Jan
ORD
Chicago
CUN
Cancun
S$421 Return, found 2 days ago
S$421
Return
found 2 days ago
Select Delta flight, departing Mon, 19 Jan from Chicago to Cancun, returning Fri, 23 Jan, priced at S$421 found 2 days ago
Delta
Wed, 18 Feb - Thu, 26 Feb
ORD
Chicago
CUN
Cancun
S$424 Return, found 7 hours ago
S$424
Return
found 7 hours ago
Select Delta flight, departing Wed, 18 Feb from Chicago to Cancun, returning Thu, 26 Feb, priced at S$424 found 7 hours ago
Delta
Mon, 19 Jan - Fri, 23 Jan
ORD
Chicago
CUN
Cancun
S$426 Return, found 2 days ago
S$426
Return
found 2 days ago
Select Delta flight, departing Mon, 19 Jan from Chicago to Cancun, returning Fri, 23 Jan, priced at S$426 found 2 days ago
American Airlines
Mon, 19 Jan - Fri, 23 Jan
ORD
Chicago
CUN
Cancun
S$428 Return, found 2 days ago
S$428
Return
found 2 days ago
Select American Airlines flight, departing Mon, 19 Jan from Chicago to Cancun, returning Fri, 23 Jan, priced at S$428 found 2 days ago
Arajet
Wed, 18 Feb - Thu, 26 Feb
ORD
Chicago
CUN
Cancun
S$434 Return, found 7 hours ago
S$434
Return
found 7 hours ago
Select Arajet flight, departing Wed, 18 Feb from Chicago to Cancun, returning Thu, 26 Feb, priced at S$434 found 7 hours ago
Air Canada
Mon, 19 Jan - Fri, 23 Jan
ORD
Chicago
CUN
Cancun
S$455 Return, found 2 days ago
S$455
Return
found 2 days ago
Select Air Canada flight, departing Mon, 19 Jan from Chicago to Cancun, returning Fri, 23 Jan, priced at S$455 found 2 days ago
United
Wed, 18 Feb - Thu, 26 Feb
ORD
Chicago
CUN
Cancun
S$459 Return, found 7 hours ago
S$459
Return
found 7 hours ago
Select United flight, departing Wed, 18 Feb from Chicago to Cancun, returning Thu, 26 Feb, priced at S$459 found 7 hours ago

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

January is typically the cheapest month to fly

From S$241 - S$442 per traveller.
Chicago to Cancun route information
Origin airport
O'Hare Intl.
Destination airport
Cancun Intl.
Airlines serving
Air Canada, American Airlines, Arajet, Delta, United, avianca
Return price
S$416
Distance
2316 km
Average flight time
4 hours 50 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$416. 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$631.60
*Available to Expedia members.