S$227 Cheap Flights from Cancun to Chicago

View S$227 flight on Sat, 24 Jan, 2026Opens in a new window

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

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Cheap Flights from Cancun to Chicago (CUN-ORD)

Prices were available within the past 7 days and start at S$227 for one-way flights and S$414 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$414 Return, found 2 days ago
S$414
Return
found 2 days ago
Select American Airlines flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$414 found 2 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$417 Return, found 2 days ago
S$417
Return
found 2 days ago
Select Delta flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$417 found 2 days ago
Delta
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$421 Return, found 2 days ago
S$421
Return
found 2 days ago
Select Delta flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$421 found 2 days ago
American Airlines
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$423 Return, found 2 days ago
S$423
Return
found 2 days ago
Select American Airlines flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$423 found 2 days ago
American Airlines
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$434 Return, found 2 days ago
S$434
Return
found 2 days ago
Select American Airlines flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$434 found 2 days ago
United
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$440 Return, found 2 days ago
S$440
Return
found 2 days ago
Select United flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$440 found 2 days ago
American Airlines
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$446 Return, found 2 days ago
S$446
Return
found 2 days ago
Select American Airlines flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$446 found 2 days ago
United
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$447 Return, found 2 days ago
S$447
Return
found 2 days ago
Select United flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$447 found 2 days ago
Arajet
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$476 Return, found 2 days ago
S$476
Return
found 2 days ago
Select Arajet flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$476 found 2 days ago
Air Canada
Fri, 5 Dec - Mon, 8 Dec
CUN
Cancun
ORD
Chicago
S$529 Return, found 2 days ago
S$529
Return
found 2 days ago
Select Air Canada flight, departing Fri, 5 Dec from Cancun to Chicago, returning Mon, 8 Dec, priced at S$529 found 2 days ago

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

January is typically the cheapest month to fly

From S$242 - S$599 per traveller.

Frequently asked questions

How much is a flight from Cancun Airport to O'Hare Airport?
Pack your bags, because round-trip flights between Cancun Airport and ORD start from S$414. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can go up quickly, so book today to secure 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 Cancun Airport to O'Hare Intl. Airport (ORD)?
This differs between air carriers, as each one has its own terms and conditions. Head to the Customer Service Portal, where there are easy instructions on how to cancel online.
How do I find cheap flights from CUN to O'Hare Intl. Airport (ORD) 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 CUN to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from CUN to O'Hare Intl. Airport (ORD)?
The flight distance from Cancun Intl. Airport (CUN) to ORD is 2,300 kilometres. Squeeze in a nap or get stuck into a book and the journey will fly by.
Which airlines fly direct from Cancun Airport to O'Hare Airport?
With a nice range of airlines to take your pick of, you should be able to find the perfect flight from Cancun Airport to O'Hare Intl. Airport (ORD) in a few easy clicks. Here are some of the top carriers with services between these airports:

  • 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 CUN to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Booking last minute from CUN to O'Hare Airport can be hit-or-miss. It is possible to find a bargain, but you could also miss out entirely! If you'd rather start planning early, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines list their prices so far in advance. Our suggestion? Check back often as prices are updated frequently.

Travel information

Origin airport
Cancun Intl.
Destination airport
O'Hare Intl.
Return price
S$413
Distance
2316 km
Average flight time
3 hours 58 mins

Book with confidence

Flights from Cancun to Chicago

There are several airlines that operate frequent flights from Cancun (CUN) to Chicago (ORD) including

The earliest flight leaves Cancun Intl. Airport at 07:00 and arrives at O'Hare Intl. Airport at 10:50. The last flight of the day departs Cancun at 19:35 and arrives at Chicago at 22:25.

The flight distance from Cancun to Chicago is about 2343 km, the shortest flight is 03 hours 45 minutes with Virgin Atlantic.

Expedia lets you search across the largest number of airlines and Chicago 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 Cancun Chicago 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 Cancun to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago 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 Cancun to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Flights from Cancun to Chicago

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