Cheap Flight Deals From Chicago (CHI) to Key West (EYW) Starting at $168

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This Weekend's Flight Deals from Chicago to Key West

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $168 One Way, $248 Round Trip from Chicago to Key West

Prices starting at $248 for return flights and $168 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.

Key West economy flight packages

Kimpton Winslow's Bungalows, an IHG Hotel
Margaritaville Beach House Key West
Ibis Bay Beach Resort
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Key West first class flight packages

Paradise Inn Key West - Adults Only
Ibis Bay Beach Resort
The Guesthouses at Southernmost Beach Resort - Adults only
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More About Flying To Key West from Chicago

Route Information for Flights from Chicago to Key West

Origin Airport IATA Code CHI
Destination Airport IATA Code EYW
Distance 1254 mi
Direct Flight Airlines American Airlines, United Airlines
Earliest Flight Arrival 7:20PM UTC
Latest Flight Arrival 8:07PM UTC

Chicago to Key West

For guaranteed low prices on flights from Chicago to Key West, search no further than Orbitz. Planning the perfect trip is simple with Orbitz; our range of bargain holiday packages and cutting edge mobile tools makes it quick and easy.

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All-in-One

With Orbitz’s Display Matrix, it is so easy to book your perfect vacation package. Just add in flights from Chicago to Key West, decide if you want hotels and car rental included and click the button! Orbitz’s Display Matrix clearly shows all the deals and great savings available, including extra discounts, such as free nights.

Cheap Flights Equals Extra Miles

Enjoy great deals on Chicago to Key West flights and rack up those air miles at the same time! With Orbitz you just add in your frequent flyer number when asked and your qualifying miles are instant. Store your number to your account profile and next time you book your miles will be automatically added.

Safeguard with our Low Price Guarantee

Feel confident when you book your Chicago to Key West 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.

Frequently asked questions

Am I able to catch a flight from Chicago to Key West now?
The Covid-19 Travel Advisor can answer all your queries about travel restrictions and quarantine when flying from Chicago to Key West.
Are there non-stop flights from Chicago to Key West?
Two carriers operate nonstop flights from Chicago, IL Airport (ORD-O’Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.) — United Airlines and American Airlines. They’ll take you where you need to go in style and comfort.
What is the shortest flight from Chicago to Key West?
The shortest flight from Midway Intl. Airport (MDW) to EYW is around 3 hours and 32 minutes. Order a wine from the drink trolley, hone your travel itinerary or get to know your seat mate — you’ll have plenty of time on this medium-haul trip.
What airlines fly from Chicago to Key West most frequently?
There are a few airlines offering frequent flights from O’Hare Airport to Key West, FL Airport (EYW-Key West Intl.), including United Airlines (UA). A top pick for many travelers, it operates 60 flights on this route each month. Alternatively, book your favorite aisle (or window) seat with American Airlines (AA). You’ll have 52 monthly flights between Chicago and Key West to choose from 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 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. 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 August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.
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 2020 saved up to 45% on their airfares. Get mixing and matching today!

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.