$159 Cheap United flights Key West (EYW) to Chicago (ORD)

Use the “Price (lowest to highest)” filter on Expedia to find cheap United Airlines return flights from $306 from EYW to ORD. Affordable one-way options from $159 are also available.**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.

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

To find cheap United Airlines fares from Key West Intl. Airport (EYW) to O’Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also impact the overall cost. Sunday is generally the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your journey on a Sunday.**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.

Jet off on one of United Airlines’s 7 weekly direct flights from Key West Intl. Airport (EYW) to O’Hare Intl. Airport (ORD). To see your choices, enter your dates, origin and destination and hit search. Then apply the “Nonstop” and “Airline” filters.

On average, it takes 3h 31m to fly nonstop from Key West Intl. Airport (EYW) to O’Hare Intl. Airport (ORD) with United Airlines.

The first flight from EYW to ORD with United Airlines departs at 3:50PM UTC-5. You’ll land at 6:21PM UTC-6. The last United Airlines flight of the day leaves at 3:50PM UTC-5 and arrives at 6:21PM UTC-6. With approximately 20% fewer cancellations for morning and mid-morning departures, jetting out early is typically 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.

United Airlines flights from Key West Intl. Airport (EYW) to Chicago come in to O’Hare Intl. Airport (ORD). This is the main entry point to this city.

Offering a rewarding loyalty program, United Airlines is a top choice for many travelers journeying from EYW to ORD. Plus, as a United Mileage Plus and One Key™ member booking through Expedia, you can earn OneKeyCash™* on eligible flights along with your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

You’ll probably travel on a Boeing 737-700 for your United Airlines flight from Key West Intl. Airport (EYW) to O’Hare Intl. Airport (ORD). However, you could end up on a different aircraft if there’s an operational need.

Depending on the type of fare you purchased, a fee is typically charged if you cancel or reschedule your flight more than 24 hours after it’s been confirmed. To secure flexible plane tickets, select our “Changes included” and “No cancel fee” boxes while searching for flights. For more details on canceling or changing your reservation, go to “Trips,” select your flight and click on “Manage Booking.”