The average bus between Chicago and South Boston takes 24h 45m and the fastest bus takes 22h 35m. The bus service runs several times per day from Chicago to South Boston. 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 Chicago and South Boston. The earliest departure is at 12:25 PM in the afternoon, and the last departure from Chicago is at 7:15 PM which arrives into South Boston at 9:50 PM. All services require a transfer, and take on average 24h 45m. The schedules shown below are for the next available departures.
Arrives next day

23h 35m • 1 change
Arrives next day

26h 35m • 1 change
Arrives next day

23h 35m • 1 change
Arrives next day

26h 35m • 1 change
Arrives next day

23h 35m • 1 change
Arrives next day

26h 35m • 1 change
Arrives next day

26h 10m • 1 change
Arrives next day

26h 35m • 1 change
Want to know about travelling from Chicago to South Boston? 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 Chicago to South Boston. However, there are services departing from Chicago station and arriving at South Boston station via Newark Penn Station station. The journey, including transfers, takes approximately 24h 45m.
Chicago to South Boston bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to South Boston bus services, operated by Flixbus USA, arrive at Boston station.
Book your Chicago to South Boston bus tickets online with Flixbus USA and Greyhound USA.
The distance between Chicago and South Boston is 1,366.4 km. The road distance is 1,748 km.
You can take a bus from Chicago Bus Station to Boston via Newark Penn Station in around 22h 30m.