Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Greyhound Lines, Inc. + FlixBus | Bus | Key West Bus Station | Chicago 95Th & Dan Ryan | Cheapest | ||||
 | Bus | Key West Bus Station | Downtown Greyhound Station | Fastest | ||||
| Bus | Key West Bus Station | Downtown Greyhound Station | No tags | ||||
| Bus | Key West Bus Station | 537-517 W. Jackson Blvd | No tags | ||||
| Bus | Key West Bus Station | Chicago 95Th & Dan Ryan | No tags |
Last refresh of the prices: Last Wednesday at 2:22 AM EST.
Get from Key West to Chicago
The journey takes about 1 day, 16 hours, and with fares starting at just $325, 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
Frequently asked questions about travelling from Key West to Chicago by bus
Please note that schedules, routes, or operator details shown here may be updated or vary 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 from $325. The average price for this route is around $437. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Key West to Chicago?
The average bus travel time from Key West to Chicago is 1d 16h, covering a distance of 1985 km. The quickest bus can get you there in 1d 11h and is operated by Greyhound.
Which bus companies service the Key West to Chicago route?
What are the earliest and latest departure times for the bus from Key West to Chicago?
The earliest bus departs from Key West to Chicago at 10:00am. And the latest bus departs at 5:00pm.
What are the CO₂ emissions for the bus trip from Key West to Chicago?
A bus trip from Key West to Chicago generates an estimated 50 kg of CO₂, making it a highly eco-friendly travel option and a mode of travel recommended by Busbud.
What is the best bus company from Key West to Chicago?
According to Busbud customers, the highest-rated bus company on this route is Greyhound, with an average rating of 3.5 out of 5 stars based on 87463 reviews.
Which bus company has the best Wi-Fi from Key West to Chicago?
Based on Busbud reviews, the bus company FlixBus has the highest Wi-Fi rating with a score of 2.7.
Which bus company has the best on-time performance from Key West to Chicago?
According to Busbud traveller reviews, the most punctual bus company on this route is FlixBus, with a punctuality rating of 3.9 out of 5 stars.
Which bus company has the cleanest buses from Key West to Chicago?
According to Busbud traveller reviews, the bus company with the cleanest buses on this route is FlixBus, with a cleanliness rating of 4.1 out of 5 stars.
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 Jan 13, 2026 with a price of $315To 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.
You can expect to pay from $315 to $394 for a bus ticket from Key West to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $315 which is on 2026-01-13.
