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
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
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 87400 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 11454 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
What's the distance between Boston and Chicago by coach?
The journey from Boston to Chicago by coach covers an approximate distance of 849 miles (1370 km).
What is the best way to go from Boston to Chicago without flying?
To travel from Boston to Chicago without flying, you can take the coaches. Choosing the coach guarantees a comfortable and sustainable travel experience, allowing you to admire the views on your way to your destination. You also have the option of utilising carpooling services.
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
£172
28/11
£180
29/11
£223
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 £714 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