Next departures for Boston to Chicago on December 26
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
151 Steel Pl, Cambridge
Chicago 95Th & Dan Ryan
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Next departures for Boston to Chicago on December 27
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Brookline
Chicago 95Th & Dan Ryan
Cheapest
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Next departures for Boston to Chicago on December 28
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
Downtown Greyhound Station
Cheapest
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Next departures for Boston to Chicago on December 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
151 Steel Pl, Cambridge
Chicago 95Th & Dan Ryan
Cheapest
Greyhound Lines, Inc. + FlixBus
Bus
Boston (South Station)
Chicago 95Th & Dan Ryan
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Next departures for Boston to Chicago on December 30
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Next departures for Boston to Chicago on December 31
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
151 Steel Pl, Cambridge
Chicago 95Th & Dan Ryan
Cheapest
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Next departures for Boston to Chicago on January 1
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Brookline
Chicago 95Th & Dan Ryan
Cheapest
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
Greyhound Lines, Inc. + FlixBus
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Last refresh of the prices: Today at 6:40 PM EST.
Compare 2 ways to go from Boston to Chicago
We recommend taking the train
Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 1 day, 2 hours 25 minutes, and with fares starting at just $118, it presents an excellent value for a comfortable ride.
Based on 87451 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 WiFi. Greyhound ticket prices on this trip start at $103
Based on 11737 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 WiFi. FlixBus ticket prices on this trip start at $102
Based on 5676 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 WiFi. Amtrak ticket prices on this trip start at $427
Frequently asked questions about travelling from Boston, MA, US to Chicago by bus
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the bus ticket from Boston to Chicago?
The cheapest bus tickets from Boston to Chicago start from $102. The average price for this route is around $163. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Boston to Chicago?
The average bus travel time from Boston to Chicago is 1d 9h, covering a distance of 1363 km. The quickest bus can get you there in 22h 22m and is operated by Amtrak.
Which bus companies service the Boston to Chicago route?
Several major bus companies operate on this route with 28 buses available per day, including services from Greyhound, FlixBus, Amtrak.
What are the earliest and latest departure times for the bus from Boston to Chicago?
The earliest bus departs from Boston to Chicago at 1:30am. And the latest bus departs at 9:50pm.
What are the CO₂ emissions for the bus trip from Boston to Chicago?
A bus trip from Boston to Chicago generates an estimated 34 kg of CO₂, making it a highly eco-friendly travel option and a mode of travel recommended by Busbud.
What is the best bus company from Boston to Chicago?
According to Busbud customers, the highest-rated bus company on this route is Amtrak, with an average rating of 4.1 out of 5 stars based on 5654 reviews.
Which bus company has the best Wi-Fi from Boston to Chicago?
Based on Busbud reviews, the bus company Amtrak has the highest Wi-Fi rating with a score of 3.6.
Which bus company has the best on-time performance from Boston to Chicago?
According to Busbud traveller reviews, the most punctual bus company on this route is FlixBus, with a punctuality rating of 3.9 out of 5 stars.
Which bus company has the cleanest buses from Boston to Chicago?
According to Busbud traveller reviews, the bus company with the cleanest buses on this route is Amtrak, with a cleanliness rating of 4.5 out of 5 stars.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
12-23
$365
12-24
$350
Today
$359
12-26
$400
12-27
$330
12-28
$268
12-29
$232
12-30
$240
The cheapest trip from Boston, MA, US to Chicago was searched and found on Dec 29, 2025 with a price of $232
To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Boston, MA, US to Chicago, as early as possible.
You can expect to pay from $232 to $521 for a bus ticket from Boston, MA, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $232 which is on 2025-12-29.
Usually Greyhound will charge you higher prices for tickets closer to the departure date. To find the best prices, you should be flexible on your date of travel.
What's the cheapest way to go from Boston, MA, US to Chicago?
The bus is the cheapest travel choice for this destination