S$184 Cheap Flights from Chicago to Cancun

View S$184 flight on Tue, 8 Jul, 2025Opens in a new window

Popular airlines from Chicago to Cancun, Quintana Roo (CUN-Cancun Intl.)

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Cheap Flights from Chicago to Cancun (CHI-CUN)

Prices were available within the past 7 days and start at S$184 for one-way flights and S$493 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 8 Jul - Fri, 11 Jul
ORD
Chicago
CUN
Cancun
S$493 Return, found 5 days ago
S$493
Return
found 5 days ago
Select American Airlines flight, departing Tue, 8 Jul from Chicago to Cancun, returning Fri, 11 Jul, priced at S$493 found 5 days ago
Delta
Tue, 8 Jul - Fri, 11 Jul
ORD
Chicago
CUN
Cancun
S$510 Return, found 5 days ago
S$510
Return
found 5 days ago
Select Delta flight, departing Tue, 8 Jul from Chicago to Cancun, returning Fri, 11 Jul, priced at S$510 found 5 days ago
American Airlines
Sat, 8 Nov - Sat, 15 Nov
ORD
Chicago
CUN
Cancun
S$513 Return, found 3 days ago
S$513
Return
found 3 days ago
Select American Airlines flight, departing Sat, 8 Nov from Chicago to Cancun, returning Sat, 15 Nov, priced at S$513 found 3 days ago
Delta
Thu, 4 Sep - Mon, 8 Sep
ORD
Chicago
CUN
Cancun
S$513 Return, found 5 days ago
S$513
Return
found 5 days ago
Select Delta flight, departing Thu, 4 Sep from Chicago to Cancun, returning Mon, 8 Sep, priced at S$513 found 5 days ago
United
Tue, 8 Jul - Fri, 11 Jul
ORD
Chicago
CUN
Cancun
S$517 Return, found 5 days ago
S$517
Return
found 5 days ago
Select United flight, departing Tue, 8 Jul from Chicago to Cancun, returning Fri, 11 Jul, priced at S$517 found 5 days ago
American Airlines
Tue, 8 Jul - Fri, 11 Jul
ORD
Chicago
CUN
Cancun
S$518 Return, found 5 days ago
S$518
Return
found 5 days ago
Select American Airlines flight, departing Tue, 8 Jul from Chicago to Cancun, returning Fri, 11 Jul, priced at S$518 found 5 days ago
American Airlines
Tue, 8 Jul - Fri, 11 Jul
ORD
Chicago
CUN
Cancun
S$521 Return, found 5 days ago
S$521
Return
found 5 days ago
Select American Airlines flight, departing Tue, 8 Jul from Chicago to Cancun, returning Fri, 11 Jul, priced at S$521 found 5 days ago
American Airlines
Sat, 8 Nov - Sat, 15 Nov
ORD
Chicago
CUN
Cancun
S$526 Return, found 3 days ago
S$526
Return
found 3 days ago
Select American Airlines flight, departing Sat, 8 Nov from Chicago to Cancun, returning Sat, 15 Nov, priced at S$526 found 3 days ago
Air Canada
Thu, 4 Sep - Mon, 8 Sep
ORD
Chicago
CUN
Cancun
S$591 Return, found 5 days ago
S$591
Return
found 5 days ago
Select Air Canada flight, departing Thu, 4 Sep from Chicago to Cancun, returning Mon, 8 Sep, priced at S$591 found 5 days ago
Aeromexico
Fri, 5 Dec - Mon, 8 Dec
ORD
Chicago
CUN
Cancun
S$844 Return, found 3 days ago
S$844
Return
found 3 days ago
Select Aeromexico flight, departing Fri, 5 Dec from Chicago to Cancun, returning Mon, 8 Dec, priced at S$844 found 3 days ago

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

January is typically the cheapest month to fly

From S$239 - S$609 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$493
Distance
2316 km

Flights from Illinois to Cancun

When looking for plane tickets from Illinois to Cancun, the ease and convenience of using Expedia simply can’t be beat. With tons of departure points and flights options from the top airline carriers, Expedia gives you the widest array of cheap flights to Cancun. Look for CHI to CUN airfare with the assurance that you have the largest online travel agency working for you.

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 Illinois 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 Illinois 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 Illinois 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 Chicago, IL (CHI-All Airports) to Cancun Airport?
Pack your bags, because round-trip journeys between Chicago, IL (CHI-All Airports) and CUN start from S$493. That's based on airfares available within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book now to get the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Chicago, IL (CHI-All Airports) to CUN?
This can vary between airlines, as each has its own terms and conditions. Visit the Customer Service Portal, where you'll find easy-to-follow instructions on how to cancel online.
How do I find cheap flights from Chicago, IL (CHI-All Airports) to CUN 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 Chicago, IL (CHI-All Airports) to CUN flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Chicago, IL (CHI-All Airports) to Cancun Intl. Airport (CUN)?
The flying distance between Chicago, IL (CHI-All Airports) and Cancun Intl. Airport (CUN) is 2,300 kilometres. Sneak in a nap or make a start on the latest bestseller and the trip will zip on by.
Which airlines fly direct from Chicago, IL (CHI-All Airports) to Cancun Airport?
Check out the deals on offer with these leading carriers and lock in your fare from Chicago, IL (CHI-All Airports) to Cancun Intl. Airport (CUN) today:
  • American Airlines - (AA) with 91 monthly flights
  • United Airlines - (UA) with 65 monthly flights
  • Southwest Airlines - (WN) with 43 monthly flights
  • Frontier Airlines - (F9) with 30 monthly flights

Are Chicago, IL (CHI-All Airports) to Cancun Airport flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Chicago, IL (CHI-All Airports) to Cancun Intl. Airport (CUN) can be hit-or-miss. You may be able to find a bargain, but then again, you could miss out entirely! If you'd prefer to play it safe and start your trip planning early, Expedia compares flight deals up to 12 months in advance. Just bear in mind that not all airlines advertise their prices that far in advance. Our top tip? Check back often as updates are made regularly.

Explore a world of travel with Expedia

Cancun Airports

Cozumel

Chicago to Cozumel Intl.
S$716.30
Chicago Airports

Chicago

O'Hare Intl. to Cancun
S$492.70
Midway Intl. to Cancun
S$840.30
*Available to Expedia members.