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Chicago, IL, USA to Key West, FL, USA from $95: 7 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Key West, United States of America

How to Get from Chicago to Key West: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$95 by busBest price
2012 kmDistance
4h 58m Fastest

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.

Company
various
Plane
Average Duration
4h  58m
Estimated price
$204-668
Recommended
Company
various
Train
Bus
Average Duration
47h  25m
Estimated price
$95-633
Cheapest
route map
Distance: 2012 km
Duration: 4h 58m

See more options

Company
various
Plane
Average Duration
6h  52m
Estimated price
$124-618
Company
various
Train
Plane
Average Duration
8h  17m
Estimated price
$287-2040
Company
various
Train
Plane
Average Duration
8h  17m
Estimated price
$347-927
Company
Palmland, FlixBus
Bus
Average Duration
34h  5m
Estimated price
$2041-2042
Company
various
Drive
Average Duration
26h 
Estimated price
$2043-2044
Browse car rentalsExplore flights

Traveling From Chicago to Key West

Embarking on a journey from Chicago, with its bustling city life and architecture, to the laid-back, sun-soaked vibes of Key West reveals a striking contrast between urban energy and island relaxation.

Best Neighbourhoods in Key West

Key West boasts vibrant neighborhoods full of character and charm.

Old Town
• Lively nightlife and many bars nearby.
• Historic architecture and landmarks throughout.
New Town
• Offers shopping and dining options galore.
• Family-friendly parks and local amenities available.
Sunset Waterside
• Stunning sunset views every evening.
• Ideal for waterfront dining and relaxation.

Best Times To Visit Key West's Attractions

Timing your visits can greatly enhance your Key West experience.

Duval Street
Visit early morning or late evening to enjoy quieter strolls and vibrant nightlife.
Mallory Square
Arrive 30 minutes before sunset for the best views without the crowds.
Ernest Hemingway Home and Museum
Weekdays early in the morning often mean fewer visitors and a serene experience.

Key West Weather: What to Expect Year-Round

Key West enjoys a tropical climate, characterized by warm temperatures and sunny days, making it an inviting destination throughout the year. However, visiting during the winter months ensures pleasant weather and fewer rain showers, enhancing your overall experience.

Dining Recommendation

At Blue Heaven, savor the iconic Key West dish of lobster eggs benedict, where fresh local seafood meets a charming outdoor setting filled with roosters and vibrant art. This contrast to Chicago's bustling dining scene offers a relaxed atmosphere, allowing you to enjoy vibrant flavors crafted from the freshest island ingredients.

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 Show flights
Website
aa.com

Plane from Chicago O'Hare to Key West

Average Duration
3h 16m
Estimated price
$2048-6681

Plane from Chicago Midway to Key West via Miami

Average Duration
5h 19m
Estimated price
$2046-6685

Plane from South Bend to Key West via Charlotte

Average Duration
5h 36m
Estimated price
$6686-6687

Plane from South Bend to Key West via Dallas/Ft.Worth

Average Duration
9h 25m
Estimated price
$6688-6689

Plane from South Bend to Key West via Chicago O'Hare

Average Duration
6h 41m
Estimated price
$950-6687

Plane from Milwaukee to Key West via Charlotte

Average Duration
5h 38m
Estimated price
$951-950

Plane from Milwaukee to Key West via Miami

Average Duration
7h 39m
Estimated price
$951-950
Website
united.com

Plane from Chicago O'Hare to Key West

Average Duration
3h 9m
Estimated price
$2043-952

Plane from Chicago O'Hare to Key West via Tampa

Average Duration
5h 22m
Estimated price
$2043-952

Plane from South Bend to Key West via Chicago O'Hare

Average Duration
5h 19m
Estimated price
$953-6687

Plane from Milwaukee to Key West via Orlando

Average Duration
5h 25m
Estimated price
$951-954
Website
delta.com

Plane from Chicago O'Hare to Key West via Atlanta

Average Duration
5h 28m
Estimated price
$2048-2049

Plane from Chicago Midway to Key West via Atlanta

Average Duration
5h 44m
Estimated price
$6680-6681

Plane from South Bend to Key West via Atlanta

Average Duration
5h 49m
Estimated price
$6682-6683

Plane from Milwaukee to Key West via Atlanta

Average Duration
5h 38m
Estimated price
$6684-2047
Train
Contact phone
+1-800-872-7245
Website
amtrak.com

Train from Chicago Union Station to Washington Union Station

Average Duration
17h 25m
Estimated price
$9590-2048

Train from Washington Union Station to Hollywood Amtrak Station

Average Duration
22h 57m
Estimated price
$6332-6682

Train from Chicago Union Station to Milwaukee

Average Duration
1h 29m
Estimated price
$9590-9575
Contact phone
+1 219-926-5744
Website
mysouthshoreline.com

Train from Van Buren St. to South Bend Airport

Average Duration
2h 35m
Estimated price
$955-956
Bus Show bus routes
Website
palmlandlines.com

Bus from Chicago IL to Miami FL

Average Duration
28h 45m
Estimated price
$1246-6337
Contact phone
+1 (855) 626-8585
Website
flixbus.com

Bus from Downtown Miami to Key West

Average Duration
4h 20m
Estimated price
$1247-9555

Bus from Miami Airport Station to Key West

Average Duration
3h 55m
Estimated price
$956-9550
Drive

Drive from Chicago to Key West

Average Duration
26h
Estimated price
$2043-2044

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.

🚗 Embark on an epic road trip from bustling Chicago to the sun-soaked paradise of Key West, covering a scenic distance of 1,543 miles over the course of approximately 26 hours behind the wheel. 💸 Budget-savvy travelers can expect car trip expenses to range from $280 to $410, offering the freedom to explore charming roadside attractions and savory local cuisine along the way.
Average price
$280 - $410
🌴 Traveling from Chicago to Key West by plane is a convenient option, with direct flights taking around 3 hours and 9 minutes. Several major airlines, including American Airlines, Silver Airways, United Airlines, and Delta, operate flights on this route. 🏖️ The total travel time to reach Key West from Chicago by plane is approximately 4 hours and 58 minutes. This allows for a relatively quick and efficient journey to the beautiful destination in Florida. 🛫 Flight prices between Key West and Chicago can vary, with tickets typically ranging from $204 to $668.
Departure Point
Chicago O'Hare Airport
Arrival Point
Key West Airport
🚌 Embark on an adventurous bus journey from Chicago to Key West, although there is no direct route available. The trip involves transfers and a layover in Downtown Miami, totaling approximately 34 hours and 5 minutes. 💵 Experience this budget-friendly travel option with bus ticket prices ranging from $96 to $164 for a one-way trip between Chicago and Key West. Sit back, relax, and soak in the beauty of the journey as you head towards your sunny destination.
Departure Point
Chicago IL station
Arrival Point
Key West station

Frequently asked questions

Find out more about the route from Chicago to Key West.

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The cheapest way to travel from Chicago to Key West is by bus. There are several bus companies that offer routes from Chicago to Key West, with prices ranging from $95 to $170. The journey takes about 34 hours and 5 minutes, so be prepared for a long ride. While it may not be the fastest option, it is a cost-effective way to reach your destination.
The fastest way to travel from Chicago to Key West is by flying. There are direct flights available, and the journey takes approximately 6 hours. The cost of the flight can vary, ranging from $220 to $1,700 depending on the airline and the time of booking. It is recommended to compare prices and book in advance to secure the best deal.
The distance between Chicago and Key West is approximately 1250 miles. If you choose to travel by road, the distance is around 1542.9 miles. This journey can be completed by car or bus, depending on your preference. Keep in mind that travel times may vary depending on the route and traffic conditions.
The best way to travel from Chicago to Key West without a car is by bus. Several bus companies offer routes from Chicago to Key West, with an average travel time of 34 hours and 5 minutes. The cost of a bus ticket generally ranges from $95 to $170. This option is convenient for those who do not want to drive or fly to their destination.
The journey from Chicago to Key West takes approximately 6 hours, including transfers. The most common way to travel this distance is by flying, with several airlines offering direct flights from Chicago to Key West. Alternatively, you can also drive, which takes around 18 hours, depending on the route and traffic conditions. Another option is to take a combination of train and bus, which may take longer but can be a more cost-effective choice for some travelers.
There are numerous accommodation options available in Key West, ranging from hotels to vacation rentals. Some popular hotel options include The Perry Hotel Key West and Ocean Key Resort & Spa. Prices for hotels in Key West start at $142 per night, and it is advisable to book in advance as the availability may vary depending on the season. Additionally, there are also vacation rental options available for those who prefer a more private stay.
Yes, it is possible to drive from Chicago to Key West. The driving distance is approximately 1543 miles and it takes around 26 hours to complete the journey. It is important to note that this is a long drive and requires proper planning, rest stops, and breaks along the way. Additionally, make sure to have a valid driver's license, insurance, and a well-maintained vehicle before embarking on this road trip.
Yes, there is no direct bus between Chicago and Key West. However, you can take a bus from Chicago to Key West with a transfer in Downtown Miami. The journey takes approximately 34 hours and 5 minutes. During the transfer, you will need to switch buses to reach Key West.
You can catch the bus from Chicago to Key West at the Chicago IL station. The bus services are operated by Palmland Bus Lines. Make sure to check the schedule and arrive at the station ahead of time to ensure a smooth departure.
The bus from Chicago to Key West arrives at Key West station. Key West station is located in the heart of downtown Key West, making it convenient for travelers to access popular tourist attractions and accommodations. From Key West station, travelers can easily explore the beautiful beaches, historic sites, and vibrant nightlife that Key West has to offer.
To get to Key West from the airport, you can take a connecting flight to Key West International Airport. There are several airlines that offer direct flights from Chicago O'Hare Airport to Key West. The flight duration is approximately 3 hours and prices can vary depending on the airline and time of booking. Once you arrive at Key West International Airport, you can easily reach the city center by taxi, shuttle service, or rental car.
United Airlines, Delta, and American Airlines all offer flights from Chicago O'Hare Airport to Key West Airport. United Airlines operates daily flights with multiple departure times, while Delta and American Airlines offer flights with varying frequencies throughout the week. It is recommended to check with the respective airlines for the most up-to-date flight schedules and prices.
The fastest way to travel from Chicago to Key West is by taking a direct flight. The quickest flight from Chicago O'Hare Airport to Key West Airport takes approximately 3 hours and 11 minutes. United Airlines, Delta, and American Airlines offer flights on this route. The flight duration from Chicago to Key West is around 6 hours. The prices for a flight between these two cities range from $224 to $1609, depending on the airline and time of booking.
The flight from Chicago to Key West typically takes around 3 hours and 11 minutes. However, it is important to note that flight durations can vary depending on factors such as weather conditions and air traffic. It is recommended to check with the airline for the most accurate and up-to-date information regarding flight times. Additionally, travelers should arrive at the airport at least 2 hours prior to their scheduled departure time to allow for check-in and security procedures.
The cost of a flight from Chicago to Key West can range from $224 to $1609. The price will depend on factors such as the airline, time of booking, and availability. It is recommended to check multiple airlines and online travel agencies to find the best deals. Additionally, booking in advance and being flexible with travel dates can help secure cheaper fares.
The cost of a bus ticket from Chicago to Key West can range between $96 to $164 depending on the bus company and the type of ticket purchased. It is recommended to book in advance to secure the best deals and lower prices. Additionally, prices may also vary depending on the time of year and demand. It is always a good idea to compare prices from different bus operators to find the most affordable option for your trip.
The cost of driving from Chicago to Key West can range from $280 to $410, depending on factors such as fuel prices and the type of vehicle you have. This estimate includes the cost of gas, tolls, and potential overnight accommodations. It's important to note that these expenses may fluctuate, so it's a good idea to budget for any unforeseen costs that may arise during the trip.

Trips from Chicago

Trips to Key West