1map logoGo to main page

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
to
Key West, United States

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

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
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
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.

Or choose the category:
The cheapest way to get from Chicago to Key West is by taking a bus. The bus journey typically costs between $95 and $170 and takes approximately 34 hours and 5 minutes.
The fastest way to travel from Chicago to Key West is by flying. The flight duration is approximately 6 hours, making it the quickest option available. The cost of a flight ticket from Chicago to Key West can range from $220 to $1700, depending on the airline and time of booking.
The distance between Chicago and Key West is approximately 2012 kilometers. If you prefer to travel by road, the distance is around 2483 kilometers.
The most convenient way to travel from Chicago to Key West without a car is by bus. There are several bus companies that offer direct routes from Chicago to Key West, with travel times varying around 34 hours and 5 minutes. The cost for a bus ticket ranges from $95 to $170, depending on the bus company and the time of year you are traveling.
The quickest way to get from Chicago to Key West is by flying. There are multiple airlines that offer direct flights, with a travel time of approximately 3 hours and 30 minutes. It is also possible to drive from Chicago to Key West, which takes around 18 hours, depending on the route and traffic conditions. Another option is to take a train and bus combination, which generally takes around 34 hours.
There are numerous accommodation options available near Key West. With over 466 hotels to choose from, travelers can find a range of options to suit their budget and preferences. Prices start at $142 per night, with choices ranging from luxury resorts to budget-friendly guesthouses and everything in between.
Yes, you can drive from Chicago to Key West. The driving distance is around 2483 km, which would take approximately 26 hours without stops.
Yes, there is no direct bus between Chicago and Key West. However, you can take a bus from Chicago to Key West with transfers in Downtown Miami. This journey typically takes around 34 hours and 5 minutes.
You can catch the bus from Chicago to Key West at the Chicago IL bus station. The bus service is operated by Palmland Bus Lines.
The bus from Chicago to Key West arrives at the Key West station.
United Airlines, Delta, and American Airlines offer flights from Chicago O'Hare Airport to Key West Airport. United Airlines operates direct flights between the two cities, while Delta and American Airlines may have layovers.
The fastest way to get from Chicago to Key West is by taking a direct flight from Chicago O'Hare Airport to Key West Airport. This flight typically takes around 3 hours and 11 minutes. United Airlines, Delta, and American Airlines are a few airlines that offer flights between these two cities. The prices for these flights can range from $224 to $1609.
The flight from Chicago to Key West takes approximately 3 hours and 11 minutes.
The cost of a flight from Chicago to Key West can range from $224 to $1609, depending on factors such as the airline, time of booking, and availability.
The cost of a bus ticket from Chicago to Key West can range from $95 to $170.
The cost to drive from Chicago to Key West varies depending on factors such as gas prices, tolls, and vehicle efficiency. On average, you can expect to spend approximately $280 to $410 on fuel for the round trip.