Next departures for Boston to Chicago on November 19
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
Boston Route 128, MA
Chicago (Union Station), IL
Cheapest
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
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 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
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
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 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
Train
Boston Route 128, MA
Chicago (Union Station), IL
Cheapest
Train
Boston Route 128, MA
Chicago (Union Station), IL
Fastest
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
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
Train
Boston Route 128, MA
Chicago (Union Station), IL
Cheapest
Amtrak Acela + Amtrak
Train
Boston Route 128, MA
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
Last refresh of the prices: Today at 6:48 AM 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 the good way to reach Chicago. The journey takes about 1 day, 7 hours 10 minutes and with fares starting at just $69, it presents an excellent value for a comfortable ride.
Based on 5591 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $85
Frequently asked questions about traveling from Boston, MA, US to Chicago by train
How much does a train ticket from Boston to Chicago cost?
The average train ticket price from Boston to Chicago is $221. The best way to find 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 trains 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 have layovers. 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 traveling between Boston and Chicago leave from Back Bay Station or South Station and arrive at Union Station.
What are the best sights and things to do in Chicago?
Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/15
$372
11/16
$1,300
Today
$405
11/18
$377
11/19
$295
11/20
No data
11/21
$613
11/22
$467
The cheapest trip from Boston, MA, US to Chicago was searched and found on Nov 19, 2025 with a price of $295
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 $295 to $2,225 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 $295 which is on 2025-11-19.