Next departures for Boston to Chicago on December 6
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 for Boston to Chicago on December 8
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 for Boston to Chicago on December 9
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 for Boston to Chicago on December 10
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 for Boston to Chicago on December 11
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 for Boston to Chicago on December 12
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 for Boston to Chicago on December 13
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 12:38 AM EST.
Compare 2 ways to go from South Station to Chicago
We recommend taking the bus
Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 6 hours 15 minutes and with fares starting at just $68, it presents an excellent value for a comfortable ride.
Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.
Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.
Based on 5627 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $102
Frequently asked questions about traveling from Boston, MA, US to Chicago by bus
How much does a bus ticket from South Station to Chicago cost?
The bus ticket price from South Station to Chicago starts at $68. 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 you 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.
What are the best sights and things to do in Chicago?
Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.
