The average bus between Key West and Chicago takes 39h 20m and the fastest bus takes 37h 31m. The bus service runs several times per day from Key West to Chicago. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Buses run twice daily between Key West and Chicago. The earliest departure is at 7:39 AM in the morning, and the last departure from Key West is at 4:15 PM which arrives into Chicago at 8:25 AM. All services require a transfer at Big Pine Key - Auto Store / NAPA MM30 and take an average of 39h 20m. The schedules shown below are for the next available departures.
Arrives next day



36h 31m • 3 changes
Arrives +2 days



40h 10m • 3 changes
Arrives next day



36h 31m • 3 changes
Arrives +2 days



40h 10m • 3 changes
Arrives next day



36h 31m • 3 changes
Arrives +2 days



40h 10m • 3 changes
Want to know about travelling from Key West to Chicago? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.
No, there is no direct bus from Key West to Chicago. However, there are services departing from Key West station and arriving at Chicago station via Big Pine Key - Auto Store / NAPA MM30. The journey, including transfers, takes approximately 39h 20m.
Key West to Chicago bus services, operated by Key West Transit, depart from N Roosevelt & 3rd Street station.
Key West to Chicago bus services, operated by Key West Transit, arrive at Chicago Bus Station.
The distance between Key West and Chicago is 1,999.9 km. The road distance is 2,507 km.
You can take a bus from N Roosevelt & 3rd Street to Chicago Bus Station via Big Pine Key - Auto Store / NAPA MM30, Big Pine Key, Miami Airport Station, and Atlanta Bus Station in around 36h 52m.