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Fares from $121 One Way, $230 Round Trip from Chicago to Key West

Prices starting at $230 for return flights and $121 for one-way flights to Key West were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Key West from Chicago

Route Information for Flights from Chicago to Key West

Origin Airport IATA CodeCHI
Destination Airport IATA CodeEYW
Distance1254 mi
Direct Flight AirlinesAmerican Airlines, United Airlines
Earliest Flight Arrival5:40PM UTC
Latest Flight Arrival8:12PM UTC

Chicago to Key West

Looking for cheap Chicago to Key West flights? Orbitz has the cheapest air fares for flights from Chicago to Key West. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

Mobile Deals and Steals

Orbitz is dedicated to providing low fares on Chicago to Key West flights. Now you can find the latest deals on-the-go with Orbitz’s mobile apps for iPhone, iPad, Android phones, and tablets. Instantly see discounted rates for hotels, cruises, vacations, and air tickets for a great vacation.

Book Hotels With Confidence

When you’re looking for hotel rooms to go with your bargain flights from Chicago to Key West, Orbitz provides you descriptions, photos, reviews, and location maps so you know exactly what you are booking. With easy-to-use Orbitz map tools, you can search for nearby hotels on your mobile device.

Access Your Flight Information Anytime

Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Chicago to Key West flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Chicago to Key West on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Chicago to Key West flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Key West. Need hotels too? You can book them last minute on your mobile phone.

Flights from Chicago to Key West - Frequently Asked Questions

Are there non-stop flights from Chicago to Key West?

Yes, you can jet from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) with American Airlines, the only airline that offers direct services on this route.

What is the shortest flight from Chicago to Key West?

With the journey from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) taking a minimum of 3 hours and 5 minutes, there's plenty of time to sit back and enjoy the experience. Grab a glass of wine and get cozy in your seat with an absorbing movie or novel.

What airlines fly from Chicago (and vicinity) to Key West most frequently?

American Airlines is the most frequent airline servicing the Chicago (and vicinity) to Key West route. Choose from 10 flights per month with this carrier.

If I am not able to travel due to COVID-19, can I cancel my flight to Key West?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Key West have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Key West with flexible change policies?

In most cases you'll have the option to reschedule your flight to Key West without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.