The average bus between South Station and Chicago takes 25h 38m and the fastest bus takes 21h 10m. The bus service runs several times per day from South Station 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 South Station and Chicago. The earliest departure is at 1:30 AM at night, and the last departure from South Station is at 5:15 PM which arrives into Chicago at 1:25 PM. All services require a transfer, and take on average 25h 38m. The schedules shown below are for the next available departures.
Arrives next day

28h 40m • 1 change
Arrives next day

20h 10m • 1 change
Arrives next day

28h 40m • 1 change
Arrives next day

20h 10m • 1 change
Arrives next day

28h 40m • 1 change
Arrives next day

20h 10m • 1 change
Arrives next day

28h 40m • 1 change
Arrives next day

20h 10m • 1 change
Want to know about travelling from South Station 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 South Station to Chicago. However, there are services departing from South Station station and arriving at Chicago station via Newark Penn Station station. The journey, including transfers, takes approximately 25h 38m.
South Station to Chicago bus services, operated by Greyhound USA, depart from Boston station.
South Station to Chicago bus services, operated by Greyhound USA, arrive at Chicago Bus Station.
Book your South Station to Chicago bus tickets online with Greyhound USA and Flixbus USA.
The distance between South Station and Chicago is 1,365.9 km. The road distance is 1,760 km.
You can take a bus from Boston to Chicago Bus Station via Newark Penn Station in around 22h 40m.