Next departures from Boston to Chicago on 6 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
South Station (Train Terminal)
Chicago (Union Station), IL
CheapestFastest
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
FlixBus + Greyhound Lines, Inc.
Boston (South Station)
Downtown Greyhound Station
No tags
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
FlixBus + Greyhound Lines, Inc.
Boston (South Station)
Downtown Greyhound Station
No tags
Next departures from Boston to Chicago on 8 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
Boston (South Station)
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Boston (South Station)
Downtown Greyhound Station
No tags
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Next departures from Boston to Chicago on 9 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
South Station (Train Terminal)
Chicago (Union Station), IL
Fastest
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Boston (South Station)
Downtown Greyhound Station
No tags
Next departures from Boston to Chicago on 10 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
South Station (Train Terminal)
Chicago (Union Station), IL
Fastest
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Downtown Greyhound Station
No tags
Next departures from Boston to Chicago on 11 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
South Station (Train Terminal)
Chicago (Union Station), IL
Fastest
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Downtown Greyhound Station
No tags
Next departures from Boston to Chicago on 12 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
South Station (Train Terminal)
Chicago (Union Station), IL
Fastest
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Downtown Greyhound Station
No tags
Next departures from Boston to Chicago on 13 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
South Station (Train Terminal)
Chicago (Union Station), IL
Fastest
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Greyhound Lines, Inc. + FlixBus
Boston (South Station)
Downtown Greyhound Station
No tags
Boston (South Station)
Downtown Greyhound Station
No tags
Last refresh of the prices: Today at 00:38 EST.
Compare 2 ways to travel from South Station to Chicago
We recommend taking the bus
Among the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 1 day, 6 hours 15 minutes and with fares starting at just £52, it presents an excellent value for a comfortable ride.
Based on 87415 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained with the Wi-Fi. Greyhound ticket prices on this trip start at £53
Based on 11536 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the staff but often complained with the Wi-Fi. FlixBus ticket prices on this trip start at £52
Based on 5627 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at £79
Frequently asked questions about travelling by bus from Boston, MA, US to Chicago
How much does a bus ticket from South Station to Chicago cost?
The bus ticket price from South Station to Chicago starts at £52. The best way to find cheap bus tickets from South Station to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the bus ride from South Station to Chicago?
The average travel time between South Station and Chicago is around , although the fastest bus will take about 22h 22m. This is the time it takes to travel the 849 miles that separates the two cities.
How many daily bus connections are there between South Station and Chicago?
The number of buses from South Station to Chicago can differ depending on the day of the week. On average, there are 20 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from South Station to Chicago by comparing and selecting the bus that fits your travel style and budget on Busbud.
Which bus companies travel from South Station to Chicago?
When taking the bus from South Station to Chicago, you can travel comfortably and safely with Greyhound, Amtrak, FlixBus.
