Next departures from Boston to Chicago on 27 November
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)
537-517 W. Jackson Blvd
Cheapest
Bus
Brookline
Chicago 95Th & Dan Ryan
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
Brookline
537-517 W. Jackson Blvd
No tags
Next departures from Boston to Chicago on 28 November
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 from Boston to Chicago on 1 December
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)
537-517 W. Jackson Blvd
Cheapest
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Bus
Boston (South Station)
537-517 W. Jackson Blvd
No tags
Next departures from Boston to Chicago on 2 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Boston (South Station)
Chicago 95Th & Dan Ryan
Cheapest
Bus
Boston (South Station)
Downtown Greyhound Station
Fastest
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Next departures from Boston to Chicago on 3 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
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)
Downtown Greyhound Station
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Next departures from Boston to Chicago on 4 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
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)
Downtown Greyhound Station
No tags
Bus
Brookline
Downtown Greyhound Station
No tags
Last refresh of the prices: Yesterday at 23:09 EST.
Compare 2 ways to travel from Boston 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, 8 hours 50 minutes and with fares starting at just £52, it presents an excellent value for a comfortable ride.
Based on 87402 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 11456 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 5608 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
Please note that timetables, routes, or operator details shown here may be updated or vary at the time of your journey.
How much is the bus ticket from Boston to Chicago?
The cheapest coach tickets from Boston to Chicago start from £52. The average price for this route is around £105. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus journey from Boston to Chicago?
The average bus journey time from Boston to Chicago is 1d 8h, covering a distance of 849 miles. The fastest bus can take 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 31 buses available per day, including services from Greyhound, FlixBus, Amtrak.
What is the earliest and latest departure time for the bus from Boston to Chicago?
The earliest bus departs from Boston to Chicago at 00:59. And the latest bus departs at 21:50.
What are the CO₂ emissions for the bus trip from Boston to Chicago?
A bus journey from Boston to Chicago produces an estimated 34 kg of CO₂, making it a highly eco-friendly choice and a mode of travel recommended by Busbud.
Which 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 5597 reviews.
Which company has the best Wi-Fi from Boston to Chicago?
Based on Busbud reviews, the bus company Amtrak has the best Wi-Fi rating with a score of 3.6.
Which bus company offers the most punctual service 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
25/11
£195
26/11
£227
Today
£171
28/11
£180
29/11
£222
30/11
£246
01/12
£158
02/12
£91
The cheapest trip from Boston, MA, US to Chicago was searched and found on 2 Dec 2025 with a price of £91
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 £91 to £713 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 £91, which is on 2025-12-02.
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