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
Train
Back Bay Station
Chicago (Union Station), IL
CheapestFastest
Train
Back Bay Station
Chicago (Union Station), IL
No tags
Train
Back Bay Station
Chicago (Union Station), IL
No tags
Train
South Station (Train Terminal)
Chicago (Union Station), IL
No tags
Train
South Station (Train Terminal)
Chicago (Union Station), IL
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
Train
Back Bay Station
Chicago (Union Station), IL
CheapestFastest
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
Chicago (Union Station), IL
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
Train
Back Bay Station
Chicago (Union Station), IL
CheapestFastest
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
Chicago (Union Station), IL
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
Train
Back Bay Station
Chicago (Union Station), IL
Cheapest
Train
Back Bay Station
Chicago (Union Station), IL
Fastest
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Next departures from Boston to Chicago on 5 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
Back Bay Station
Chicago (Union Station), IL
CheapestFastest
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Next departures from Boston to Chicago on 6 December
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
Back Bay Station
Chicago (Union Station), IL
CheapestFastest
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Train
Boston Route 128, MA
Chicago (Union Station), IL
No tags
Last refresh of the prices: Yesterday at 17:31 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 £53, it presents an excellent value for a comfortable ride.
Based on 5618 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 £66
Frequently asked questions about travelling from Boston, MA, US to Chicago by train
How much does a cheap train ticket from Boston to Chicago cost?
The average train ticket price from Boston to Chicago is £152. The best way to find cheap train tickets from Boston to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Boston to Chicago?
A train trip between Boston and Chicago is around 1d 2h, although the fastest train will take about 22h 15m. This is the time it takes to travel the 849 miles that separates the two cities.
How many daily train are there between Boston and Chicago?
The number of trains from Boston to Chicago can differ depending on the day of the week. On average, there are 8. Some trains are direct while others include transferring trains. Simplify your train trip from Boston to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Boston to Chicago?
When taking the train from Boston to Chicago, you can travel comfortably and safely with Amtrak.
What are the departure and arrival stations for a train from Boston to Chicago?
Trains travelling between Boston and Chicago leave from Back Bay Station or North Station and arrive at Union Station.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
29/11
£544
30/11
£544
Today
£228
02/12
£156
03/12
£130
04/12
£158
05/12
£156
06/12
£110
The cheapest trip from Boston, MA, US to Chicago was searched and found on 6 Dec 2025 with a price of £110
To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Boston, MA, US to Chicago as early as possible.
You can expect to pay from £110 to £1,686 for a train 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 £110, which is on 2025-12-06.