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Fares from $135 One Way, $293 Round Trip from Key West to Chicago

Prices starting at $293 for return flights and $135 for one-way flights to Chicago 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 Chicago from Key West

Flights from Key West to Chicago - Frequently Asked Questions

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

There sure are, which is great news if you're not a fan of stopovers. United Airlines and American Airlines operate direct flights from Key West, FL (EYW-Key West Intl.) to Chicago, IL (ORD-O'Hare Intl.).

What is the shortest flight from Key West to Chicago?

From Key West, the thrilling sights and sounds of Chicago are at least 3 hours and 15 minutes away. Book your favorite seat, or perhaps even one with a bit more legroom, and fly to your destination in comfort.

What airlines have the most flights from Key West to Chicago?

United Airlines (UA) offers 37 flights every month between Key West, FL (EYW-Key West Intl.) to Chicago, IL (ORD-O'Hare Intl.). Your next exciting adventure is only a few clicks away. Alternatively, secure your favorite seat with American Airlines (AA). You'll have 22 monthly flights between Key West and Chicago to choose from with this airline.

Route Information for Flights from Key West to Chicago

Origin Airport IATA CodeEYW
Destination Airport IATA CodeCHI
Distance1254 mi
Direct Flight AirlinesAmerican Airlines, United Airlines
Earliest Flight Arrival8:57PM UTC
Latest Flight Arrival7:54PM UTC

Flights Review

Jun 1, 2018

Flight attendant stepped in and addressed my elderly fathers shivering by turning up the heat in our area. He also found a blanket for him quickly. We had accidentally packed his coat in the checked bag.

May 8, 2018

Had no idea we had to pay for carry on! It made it not such a good price after all will never fly this again

May 2, 2018

I don't normally fly with United but I will more in the future mainly because I was so impressed with your in-flight United WiFi that provided entertainment that we could enjoy on our phones etc. My only complaint is the location to charge our devices is in a terrible spot below your seat where it is very difficult to even see the outlet to plug in your phone. They should be moved to where your feet are so you can see them.

Feb 18, 2018

Most of those don’t apply. I didn’t check a bag, could not upgrade, there wasn’t and wifi.

Feb 15, 2018

flights on time and LOVE the nonstop service between ORD-EYW!!

Key West to Chicago

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Safeguard with our Low Price Guarantee

Feel confident when you book your Key West to Chicago flights, a great hotel or a full vacation package that you are getting the best deal around. Orbitz’s low price guarantee assures you of peace of mind.

^Savings based on all package bookings with Flight + Hotel made on 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.