$144 Cheap flight deals from Chicago (CHI) to Key West (EYW)
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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 $144 One Way, $249 Round Trip from Chicago to Key West
Prices starting at $249 for return flights and $144 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
Key West first class flight packages
Southernmost Beach Resort
Jun 8 - Jun 13
Chicago (ORD) to Key West (EYW)
Reviewed on Apr 1, 2025
Almond Tree Inn Hotel - Adults Only
Jun 8 - Jun 13
Chicago (ORD) to Key West (EYW)
Reviewed on Feb 18, 2025
Orchid Key Inn - Adults Only
Jun 8 - Jun 13
Chicago (ORD) to Key West (EYW)
Reviewed on Jan 20, 2025
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 |
Earliest Flight Arrival | 4:22PM UTC |
Latest Flight Arrival | 4:22PM 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
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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.
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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.
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Top Trending
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.