Previously seen journeys
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Greyhound + FlixBus | Bus | Caroline St | 537-517 W. Jackson Blvd | No tags | ||||
FlixBus + Greyhound | Bus | Caroline St | Downtown Greyhound Station | No tags | ||||
FlixBus + Greyhound | Bus | Caroline St | Chicago 95Th & Dan Ryan | No tags | ||||
Greyhound + FlixBus | Bus | Caroline St | Downtown Greyhound Station | No tags | ||||
 | Bus | Key West Bus Station | Downtown Greyhound Station | No tags |
Get from Key West to Chicago
The journey takes about 1 day, 16 hours, and with fares starting at just R 4 345, it presents an excellent value for a comfortable ride.
Where are the popular stops in Key West and Chicago?
Stops in Key West
- A908 Caroline St, Key West, FL 33040, USA
- B
EYW Airport
3535 Florida A1A, Key West, FL 33040, USA
Stops in Chicago
- A630 W Harrison St, Chicago, IL 60607, USA
- C
Polk St & Canal St
500-536 W Polk St, Chicago IL 60607, USA - D
Tornado Bus S Kedzie Ave
2807 S Kedzie Ave, Chicago, IL 60623, USA - E
Cumberland CTA
5800 N Cumberland Ave, Chicago, IL 60631, USA - F
Turimex California Ave
2139 S California Ave, Chicago, IL 60608, USA
Compare bus companies
Based on 87531 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained about the Wi-Fi. Greyhound ticket prices on this trip start at R 5 489
Frequently asked questions about travelling from Key West to Chicago by bus
Please note that timetables, routes, or operator details shown here may be updated or differ at the time of your trip.
How much is the bus ticket from Key West to Chicago?
The cheapest bus tickets from Key West to Chicago start at R 4 345. The average price for this route is around R 5 211. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Key West to Chicago?
The average bus journey time from Key West to Chicago is 1d 16h, covering a distance of 1985 km. The fastest bus gets you there in 1d 16h and is operated by Greyhound.
Which bus companies service the Key West to Chicago route?
Several major bus companies operate on this route with 5 buses available per day.
What is the earliest and latest departure time for the bus from Key West to Chicago?
The earliest bus departs from Key West to Chicago at 10:00. And the latest bus departs at 17:00.
What are the CO₂ emissions for the bus trip from Key West to Chicago?
A bus trip from Key West to Chicago produces an estimated 49.612700000000004 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Key West to Chicago was searched and found on 04 Apr 2026 with a price of R 6 162To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Key West to Chicago as early as possible.
