- Must visit
Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum lets visitors tour the writer's residence, gardens, and rooms tied to his Key West years.
The best way to find a cheap bus ticket from Chicago, IL to Key West, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Key West, FL will cost around CHF 221 if you buy it on the day, but the cheapest tickets can be found for only CHF 221.
On Tue, Nov 03, we found 1 buses from Chicago, IL to Key West, FL, including 1 direct services.
On Tue, Nov 03 the direct buses cover the 1998 km distance in an average of 1 d 22 h 30 m but if you time it right, some buses will get you there in just 1 d 22 h 30 m .
On Tue, Nov 03 the slowest buses will take 1 d 22 h 30 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

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Buses from Chicago, IL to Key West, FL run on average 3 times per day, taking around 33h 43m. Cheap bus tickets for this journey start at CHF 89 if you book in advance.
The earliest bus runs at 10:00, the last at 17:00. The fastest bus covers the 1241 miles (1998 km) distance in 32h 20m.
Plan this route
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Chicago, IL to Key West, FL.
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator FlixBus | Departure Time 12:00AM | Arrival Time 02:30PM | Duration 38h30 | Departure days Sat | Cheapest price CHF 247 |
Operator Greyhound | Departure Time 10:15AM | Arrival Time 09:30AM | Duration 46h15 | Departure days Wed | Cheapest price CHF 206 |
Operator Greyhound | Departure Time 02:45PM | Arrival Time 09:30AM | Duration 41h45 | Departure days Wed | Cheapest price CHF 208 |
Operator Greyhound | Departure Time 03:00PM | Arrival Time 01:30PM | Duration 46h30 | Departure days Tue, Fri, Sat | Cheapest price CHF 128 |
Operator Greyhound | Departure Time 03:15PM | Arrival Time 01:30PM | Duration 46h15 | Departure days Fri | Cheapest price CHF 264 |
Operator FlixBus | Departure Time 11:00PM | Arrival Time 01:30PM | Duration 38h30 | Departure days Thu, Sat | Cheapest price CHF 176 |
The table below shows live departures for Chicago, IL to Key West, FL buses for tomorrow, Tuesday, November 3. You can also manually refresh the results below to see updated bus journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 3:00 PM Chicago, IL | 46h30 | 1:30 PM Key West, FL | 0 transfersDirect | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Buses from Chicago, IL to Key West, FL with Greyhound and FlixBus. Overnight buses available on this route with Greyhound and FlixBus. Use the details below to compare onboard facilities.
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
Discover the best of Key West, FL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Key West, FL trip today.
The Ernest Hemingway Home and Museum lets visitors tour the writer's residence, gardens, and rooms tied to his Key West years.
The Key West Butterfly and Nature Conservatory features a glass habitat with butterflies, birds, and tropical plants in a calm setting.
The Key West Museum of Art and History at the Custom House presents island history, art, and rotating exhibitions in a grand landmark building.
Duval Street is Key West's main historic thoroughfare, lined with shops, galleries, and lively architecture across the old town.
Mallory Square is a waterfront plaza known for harbor views, public space, and easy access to the historic seaport district.
Fort Zachary Taylor Historic State Park combines a coastal fort, walking paths, shaded grounds, and one of the island's best natural beaches.
Tangy pie made with Key lime juice, sweetened condensed milk, and a graham cracker crust. It is the island's signature dessert and a classic Florida Keys specialty.
Fresh local pink shrimp, usually simply peeled and chilled or lightly cooked. They are prized in the Keys for their sweet flavor and local waters.
Whole snapper, often yellowtail, seasoned and grilled or baked. It reflects Key West's strong fishing culture and the abundance of fresh local catch.
Polished seafood restaurant focused on Florida fish, oysters, and seasonal ingredients in a refined but approachable dining room.
Beloved casual spot for Cuban coffee, breakfast, sandwiches, and Cuban toast. A dependable choice for everyday local flavors.
Historic seafood house known for pink shrimp, conch dishes, and classic Key lime pie in a lively, casual Old Town setting.
Very pricey versus many US beach towns; hotels, seafood, and drinks run high, while transit is limited and parking can add costs.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and small change at cafes.
Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Key West, FL.
Find answers to the most common questions about traveling from Chicago, IL to Key West, FL by bus. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest bus, the cheapest option, or tips for making the most of your visit at Key West, FL, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Key West, FL buses use the Chicago, Union Station (Amtrak) to Key West, South Roosevelt Boulevard (Key West International Airport) station pair. Use this guide to compare Chicago, IL and Key West, FL bus stations on this route, check city-centre transport, alongside checking practicalities like bus station facilities and services.
Chicago, Greyhound Bus Station is 2 km from Chicago city centre. Public transport options include:
Chicago, Greyhound Bus Station has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food options include: Snack shop and vending machines available
Free Wi-Fi in waiting area. ATMs are located near entrance.
Ticket office support is available at Chicago, Greyhound Bus Station.
Available at Chicago, Greyhound Bus Station: Parking, Taxis, WC.
Accessibility facilities are available at Chicago, Greyhound Bus Station: Wheelchair accessible entrances and seating.
Chicago, Union Station (Amtrak) is 3 km from Chicago city centre. Public transport options include:
Chicago, Union Station (Amtrak) has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food options include: Multiple dining options are available inside the station.
Free Wi-Fi is available in waiting areas. ATMs are aTMs are located near the main entrance.
Ticket office support is available at Chicago, Union Station (Amtrak).
Available at Chicago, Union Station (Amtrak): Parking, Taxis, WC.
Accessibility facilities are available at Chicago, Union Station (Amtrak): Station is accessible with elevators and ramps.
Key West, South Roosevelt Boulevard (Key West International Airport) is 2 km from Key West city centre. Public transport options include:
Key West, South Roosevelt Boulevard (Key West International Airport) has practical services for this route, including Wifi, Parking, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Wi-Fi is available at Key West, South Roosevelt Boulevard (Key West International Airport). ATMs are available at Key West, South Roosevelt Boulevard (Key West International Airport).
Ticket office support is available at Key West, South Roosevelt Boulevard (Key West International Airport).
Available at Key West, South Roosevelt Boulevard (Key West International Airport): Parking, Taxis, WC.
Accessibility facilities are available at Key West, South Roosevelt Boulevard (Key West International Airport): The station is wheelchair accessible.
Check bus stations information for Chicago, IL and Key West, FL, including where buses depart and arrive on this route.