Chicago, IL, USA to Key West, FL, USA from $95: 7 ways by bus, train, flight or car
Compare Travel Options and Prices
How to Get from Chicago to Key West: Cheapest, Fastest and Best Way
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Compare Train, Bus, Flight, and Driving Options
Get detailed, step-by-step directions below for your trip from Chicago to Key West with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.
Chicago - Key West operators
Explore transport companies operating between Chicago and Key West, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.
Plane from Chicago O'Hare to Key West
Plane from Chicago Midway to Key West via Miami
Plane from South Bend to Key West via Charlotte
Plane from South Bend to Key West via Dallas/Ft.Worth
Plane from South Bend to Key West via Chicago O'Hare
Plane from Milwaukee to Key West via Charlotte
Plane from Milwaukee to Key West via Miami
Plane from Chicago O'Hare to Key West
Plane from Chicago O'Hare to Key West via Tampa
Plane from South Bend to Key West via Chicago O'Hare
Plane from Milwaukee to Key West via Orlando
Plane from Chicago O'Hare to Key West via Atlanta
Plane from Chicago Midway to Key West via Atlanta
Plane from South Bend to Key West via Atlanta
Plane from Milwaukee to Key West via Atlanta
Train from Chicago Union Station to Washington Union Station
Train from Washington Union Station to Hollywood Amtrak Station
Train from Chicago Union Station to Milwaukee
Train from Van Buren St. to South Bend Airport
Bus from Chicago IL to Miami FL
Bus from Downtown Miami to Key West
Bus from Miami Airport Station to Key West
Drive from Chicago to Key West
Chicago to Key West: Overview of Bus, Train, Flight, and Car Trips
Traveling between Chicago and Key West offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.
Frequently asked questions
Find out more about the route from Chicago to Key West.