Next departures for Boston to Chicago on November 20
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
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
Brookline
Downtown Greyhound Station
No tags
Next departures for Boston to Chicago on November 21
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 November 22
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 November 24
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
CheapestFastest
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
FlixBus + Greyhound Lines, Inc.
Bus
Boston (South Station)
Downtown Greyhound Station
No tags
Next departures for Boston to Chicago on November 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
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: Last Saturday at 3:01 PM EST.
Compare 2 ways to go 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, 7 hours 20 minutes, and with fares starting at just $97, it presents an excellent value for a comfortable ride.
Based on 87384 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 $99
Based on 11380 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 WiFi. FlixBus ticket prices on this trip start at $97
Based on 5594 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 $147
Frequently asked questions about travelling from Boston, MA, US to Chicago by bus
What is the distance between Boston and Chicago?
Boston and Chicago are 1370 km (849 miles) apart.
What are the departure and arrival locations for buses traveling from Boston to Chicago?
Buses departing from Back Bay Station in Boston will take you to Downtown Greyhound Station in Chicago.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11-18
$258
11-19
$271
Today
$230
11-21
$361
11-22
$277
11-23
$184
11-24
$227
11-25
$388
The cheapest trip from Boston, MA, US to Chicago was searched and found on Nov 23, 2025 with a price of $184
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 $184 to $1,328 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 $184 which is on 2025-11-23.
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