$142 Cheap American Airlines flights Cancun (CUN) to Chicago (ORD)

Apply the “Price (lowest to highest)” filter on Expedia to search for cheap American Airlines round-trip flights from $244 from CUN to ORD. Affordable one-way fares from $142 are available as well.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

American Airlines flights to Chicago are typically cheaper in the quieter months of January and February. Whether you’re in search of a round-trip or one-way ticket, you could find a better deal then.

To find cheap flights from CUN to ORD with American Airlines, begin searching about one month before your intended departure. You can save 17% when you book your international tickets 18 to 29 days ahead instead of booking four to five months in advance. Another helpful tip? Booking on Sunday can lead to average savings of 17% compared to Friday (the most expensive day).**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

Choose from one of American Airlines’s 12 direct weekly flights from Cancun Intl. Airport (CUN) to O’Hare Intl. Airport (ORD). To see your options, enter your origin, dates and destination and hit search. Then select the “Nonstop” and “Airline” filters.

It takes around 4h 5m to fly nonstop from Cancun Intl. Airport (CUN) to O’Hare Intl. Airport (ORD) with American Airlines.

If you’re looking for flexibility, Thursday offers the most choice for American Airlines flights from Cancun Intl. Airport (CUN) to O’Hare Intl. Airport (ORD). Take your pick of 2 different departures.

The first American Airlines flight from CUN to ORD departs at 2:33PM UTC-5, landing at 5:38PM UTC-6. If you want to head off later in the day, the last American Airlines flight leaves CUN at 3:47PM UTC-5 and lands at ORD at 6:52PM UTC-6. Flying earlier is generally a good option as morning and mid-morning flights tend to experience fewer cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

American Airlines flights from Cancun Intl. Airport (CUN) to Chicago touch down at O’Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). The primary Chicago gateway serviced by this airline is ORD. It’s worth exploring flights landing at nearby airports on Expedia as there may be lower prices.

Most likely, you’ll catch a Boeing 737-800 for your American Airlines flight from Cancun Intl. Airport (CUN) to O’Hare Intl. Airport (ORD). However, you may end up on a different aircraft for operational reasons.

Changes are usually free within 24 hours of booking, but your airline may charge a fee after that. For further information about altering your flights, check out your “Trips,” select your flight and click on “Manage Booking.” If you want the flexibility to change your itinerary without being charged, tick the “Changes included” or “No cancel fee” filter when organizing your next break.