Cheap Flight Deals From Chicago (CHI) to Key West (EYW) Starting at $117

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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 $117 One Way, $213 Round Trip from Chicago to Key West

Prices starting at $213 for return flights and $117 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

Paradise Inn Key West-Adults Only
Almond Tree Inn Hotel - Adults Only
Oceans Edge Key West Resort, Hotel & Marina
Don't see what you're looking for?
See all available trips from Chicago to Key West
View all trips

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 5:57PM UTC
Latest Flight Arrival 7:10PM UTC

Chicago to Key West

Trip-Planning Made Easy

Your search engine may give you thousands of pages of results when you search for cheap flights from Chicago to Key West, but you can save yourself a lot of hassle and money by going straight to Orbitz.com. Not only do we offer great deals on Chicago to Key West flights, but we make it easy to book hotels, car rentals, cruises, or a complete vacation package of your dreams.

Discount Chicago to Key West Flights

Orbitz’s low price guarantee means you get the best fares around. Find the lowest prices for international and domestic tickets and for flights from Chicago to Key West when you use Orbitz. It’s easy to add activities to your booking, so you can take advantage of all that Key West has to offer.

Easily Book, Change, Cancel Flights From Chicago to Key West

Orbitz now offers free mobile device apps, so even the busiest multi-taskers can plan their vacations while away from their desktop computer. Plus, instant alerts to your email or mobile phone help you stay on top of any delays or travel updates, so you avoid unpleasant surprises before boarding your Chicago to Key West flights. Our Customer Service representatives are ready to assist you if you need to change your air travel plans.

Take Advantage of Frequent Flyer Options Through Orbitz

With Orbitz, you do not have to choose between a low fare and earning frequent flyer miles. Simply provide your frequent flyer information when you book your Chicago to Key West flights.

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.