$149 Cheap United flights Cancun (CUN) to Chicago (ORD)

Scoring cheap one-way United Airlines flights from CUN to ORD from $149 on Expedia couldn't be simpler — just filter by "Price (lowest to highest)." Alternatively, check out our affordable return fares from $246 for your next getaway.**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.

Scoring the best United Airlines deals from CUN to ORD often comes down to booking at the right time. You can save 17% on international flights when you book 18 to 29 days before takeoff instead of four to five months ahead. To top it off, you can pocket 17% on average by buying your fare on a Sunday rather than a Friday, which is often the most expensive day to book.* It's a good idea to start checking out flights about one month before you want to travel.*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.

The first flight from CUN to ORD with United Airlines departs at 1:27PM UTC-5. You'll land at 4:23PM UTC-6. The final United Airlines flight of the day leaves at 4:40PM UTC-5 and arrives at 7:36PM UTC-6. With around 20% fewer cancellations for morning and mid-morning flights, starting your travel day early is often the wisest option.**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.

Travel from CUN to ORD with United Airlines and you can look forward to a range of perks starting with a rewarding loyalty program. When booking through Expedia as a United Mileage Plus and One Key™ member, you could also earn OneKeyCash™* to use on select future travel purchases.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.