A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.

Cheap Flights from Cancun (CUN) to Chicago (ORD)

View AU$318 flight on Thu, 23 July 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 35% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Cancun (CUN) to Chicago (ORD)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Aeromexico
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$545 Return, found 6 days ago
AU$545
Return
found 6 days ago
Select Aeromexico flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$545 found 6 days ago
Delta
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$553 Return, found 6 days ago
AU$553
Return
found 6 days ago
Select Delta flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$553 found 6 days ago
American Airlines
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$612 Return, found 6 days ago
AU$612
Return
found 6 days ago
Select American Airlines flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$612 found 6 days ago
American Airlines
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$620 Return, found 6 days ago
AU$620
Return
found 6 days ago
Select American Airlines flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$620 found 6 days ago
Delta
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$634 Return, found 6 days ago
AU$634
Return
found 6 days ago
Select Delta flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$634 found 6 days ago
Delta
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$640 Return, found 6 days ago
AU$640
Return
found 6 days ago
Select Delta flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$640 found 6 days ago
Aeromexico
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$642 Return, found 6 days ago
AU$642
Return
found 6 days ago
Select Aeromexico flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$642 found 6 days ago
United
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$643 Return, found 6 days ago
AU$643
Return
found 6 days ago
Select United flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$643 found 6 days ago
Delta
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$648 Return, found 6 days ago
AU$648
Return
found 6 days ago
Select Delta flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$648 found 6 days ago
Air Canada
Wed, 2 Sept - Mon, 7 Sept
CUN
Cancun
ORD
Chicago
AU$713 Return, found 6 days ago
AU$713
Return
found 6 days ago
Select Air Canada flight, departing Wed, 2 Sept from Cancun to Chicago, returning Mon, 7 Sept, priced at AU$713 found 6 days ago

Frequently asked questions

How much does a flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find one-way and return flights from CUN to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when CUN to ORD ticket fares go up or down.
What is the cheapest month to fly from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD)?
The cheapest months to fly from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are 5 airlines offering direct flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.). Here are some of the top carriers:
  • United operates 18 direct flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • American Airlines operates 14 direct flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • Frontier Airlines operates 7 direct flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • Southwest Airlines operates 7 direct flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • Spirit Airlines operates 7 direct flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
How do I find cheap flights from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD)?
To find a cheap flight from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, Spirit Airlines offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. American Airlines offers the most daily flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
October is a fantastic time to fly from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD). It's one of the cheapest months, with return flights averaging around AU$464, and it's also a popular time to travel, meaning you'll have plenty of flight options to choose from. If you're looking for another affordable option, February also offers similar low prices.
How many flights per day from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll find approximately 6 nonstop flights per day from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.). For even more choices, look at flights that include layovers, as there are around 116 connecting flights per day. Some common connection points include Mexico City Intl. (MEX), Dallas-Fort Worth Intl. (DFW), and Pearson Intl. (YYZ).
What is the earliest flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 12:10 AM local time, operated by Viva. This is a seasonal service active in January. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you're flying from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.), you'll typically find the most flights on a Sunday, with around 86 flights available. This gives you plenty of options to choose from for your travel plans. Major airlines on this route include Delta, American Airlines, and Viva. Flight options are notably more plentiful on Sundays compared to other days of the week, offering you greater flexibility.
What are the most popular departure times for flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the afternoon, from 12pm to 3pm. Many major carriers, including American Airlines, Delta and United, offer flights during this window. Many travelers prefer this because it allows for a relaxed morning before heading to the airport, and you'll arrive in Chicago in the late afternoon or early evening.
How long does it take to fly from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically takes around 4 hours. This route covers a distance of approximately 2,330 kilometers. If you opt for a flight with one stop, your travel time will be longer, usually around 7 hours 30 minutes. Flights with two or more stops can take significantly longer, often around 23 hours. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some flexibility in your travel plans.
Can you fly business or first class from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Yes, you can fly business class or first class between CUN and ORD. Airlines that offer business class service on this route include:
  • Frontier Airlines
  • Aeromexico
  • Air Canada
  • Avianca
  • United
  • Delta
  • American Airlines
First class cabins are available on Alaska Airlines and Spirit Airlines.
How do I earn miles on a Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) flight with Expedia?
It's easy to earn miles on a Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (ORD) from Cancun, Quintana Roo (CUN)?
If you're planning to travel to Chicago from Cancun Intl. (CUN), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Los Angeles Intl. (LAX), Seattle - Tacoma Intl. (SEA), or San Francisco Intl. (SFO) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) at the last minute?
Typically, booking a last minute flight from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) flight and hotel package?
Securing a Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Cancun, Quintana Roo (CUN) to Chicago, IL (ORD)?
If you booked your Cancun, Quintana Roo (CUN) to Chicago, IL (ORD) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Cancun Intl.
Destination airport
O'Hare Intl.
Return price
AU$544
Distance
2316 km
Average flight time
4 hours 6 mins

Book with confidence

Your quick guide to flights from Cancun to Chicago

Pick up great flights from Cancun to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Cancun to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Cancun to Chicago that take around hours.

Find cheap flights from Cancun to Chicago

From the great flight deals with prices currently ranging from AU$545 to AU$713, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Cancun to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in September.

Reasons to book your flight from Cancun to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Cancun to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Your quick guide to flights from Cancun to Chicago

Explore a world of travel with Expedia

*Available to Expedia members.