Cheap Flight Deals From Chicago (CHI) to Key West (EYW) Starting at $134

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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 $134 One Way, $217 Round Trip from Chicago to Key West

Prices starting at $217 for return flights and $134 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

Ambrosia Key West
Hilton Garden Inn Key West,The Keys Collection
Courtyard by Marriott Key West Waterfront
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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 5:50PM UTC
Latest Flight Arrival 6:54PM UTC

Chicago to Key West

Whether you want to book cheap flights from Chicago to Key West or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to Key West flights.

Make the Most of Your Vacation

Not only does Orbitz have cheap deals for Chicago to Key West flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Key West.

Planning on the Go

Book your flights from Chicago to Key West wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Chicago to Key West flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

Craft Your Perfect Vacation

Orbitz takes the stress out of vacation planning with great deals on flights from Chicago to Key West, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.

Keep Informed With Orbitz

With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Chicago to Key West flights. The alerts can be sent straight to your mobile phone or email.

Frequently asked questions

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.