Next departures for Chicago to Boston on November 26
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Downtown Greyhound Station
Brookline
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Bus
Chicago 95Th & Dan Ryan
Brookline
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
151 Steel Pl, Cambridge
No tags
Next departures for Chicago to Boston on November 27
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Bus
Downtown Greyhound Station
Brookline
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Next departures for Chicago to Boston on November 28
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Downtown Greyhound Station
Boston (South Station)
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Bus
Downtown Greyhound Station
Brookline
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
151 Steel Pl, Cambridge
No tags
Next departures for Chicago to Boston on November 29
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Bus
Downtown Greyhound Station
Brookline
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Next departures for Chicago to Boston on November 30
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Chicago 95Th & Dan Ryan
Brookline
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Bus
Downtown Greyhound Station
Brookline
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Next departures for Chicago to Boston on December 1
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Brookline
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Boston (South Station)
Fastest
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Downtown Greyhound Station
Brookline
No tags
Next departures for Chicago to Boston on December 2
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Downtown Greyhound Station
Brookline
Cheapest
Bus
Downtown Greyhound Station
Boston (South Station)
Fastest
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Greyhound Lines, Inc. + FlixBus
Bus
537-517 W. Jackson Blvd
Brookline
No tags
Bus
537-517 W. Jackson Blvd
Boston (South Station)
No tags
Next departures for Chicago to Boston on December 3
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Brookline
Cheapest
Bus
Downtown Greyhound Station
Boston (South Station)
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Downtown Greyhound Station
Boston (South Station)
No tags
Bus
537-517 W. Jackson Blvd
Boston (South Station)
No tags
Greyhound Lines, Inc. + FlixBus
Bus
Downtown Greyhound Station
Brookline
No tags
Last refresh of the prices: Last Monday at 5:43 AM CST.
Compare 2 ways to go from Chicago to Boston
We recommend taking the train
Among the sustainable travel choices, the train stands out as the good way to reach Boston. The journey takes about 1 day, 2 hours 18 minutes and with fares starting at just $85, 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.
Greyhound Chicago Boston recent customer reviews
Good services, Caring Drivers, but buses not on time, i missed my 1pm bus to Boston because the bus to newyork didnt arrive on time
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.
Frequently asked questions about traveling from Chicago to Boston, MA, US by bus
What is the travel distance from Chicago to Boston?
The distance separating Chicago and Boston is 849 miles (1370 km).
What are the departure and arrival stations when taking the bus from Chicago to Boston?
The majority of buses traveling from Chicago to Boston start their journey at Downtown Greyhound Station and wind up at Back Bay Station. These are the most popular pick-up and drop-off locations on this route, but you can find others that could fit better into your travel plans.
What are the best sights and things to do in Boston?
Once in Boston, you can start exploring the city and discover its surroundings. The top sights and things to do are Boston Celtics at TD Garden, Museum of Fine Art, New England Aquarium, Boston Blazers at TD Garden and Boston Red Sox at Fenway Park.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/24
$309
11/25
$334
Today
$203
11/27
$180
11/28
$202
11/29
$387
11/30
$264
12/01
$171
The cheapest trip from Chicago to Boston, MA, US was searched and found on Dec 1, 2025 with a price of $171
To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Chicago to Boston, MA, US, as early as possible.
You can expect to pay from $171 to $428 for a bus ticket from Chicago to Boston, MA, US based on the last 2 days. You can expect to find the cheapest price for the trip at $171 which is on 2025-12-01.
What's the cheapest way to go from Chicago to Boston, MA, US?
The bus is the cheapest travel choice for this destination