The cheapest and fastest trains from Brookline, MA to Chicago, IL
Cheapest price
$292
Average price
$292
Fastest journey
21 h 15 m
Average duration
21 h 15 m
Trains per day
1
Distance
1363 km
The best way to find a cheap train ticket from Brookline, MA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Brookline, MA to Chicago, IL will cost around $292 if you buy it on the day, but the cheapest tickets can be found for only $292.
Of the 1 trains that leave Brookline, MA for Chicago, IL on Fri, Nov 28, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Nov 28 the direct trains cover the 1363 km distance in an average of 21 h 15 m but if you time it right, some trains will get you there in just 21 h 15 m .
On Fri, Nov 28 the slowest trains will take 21 h 15 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.


Live departures
Brookline, MA to Chicago, IL train times
The table below shows live departures for Brookline, MA to Chicago, IL trains for today, Thursday, November 27. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 12:57 PM Brookline, MA | 21h15 | 10:12 AM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Brookline, MA to Chicago, IL by train
Compare train prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Nov 28
Nov 29
Nov 30
Dec 01
Dec 02
Dec 03
Dec 04
Why should you book Brookline to Chicago trains with Omio?
Amtrak operates all train services from Brookline to Chicago. Omio is the only official third party seller for Amtrak tickets.
Why book with Omio vs Amtrak?
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
Why book with Omio over Trainline and Rail Europe?
- Official reseller: Amtrak tickets can only be bought on Omio or Amtrak's website as Omio is the only official third party seller for Amtrak tickets. Trainline, RailEurope, and Rail.Ninja do not sell Amtrak tickets as they are not official sellers.
Journey information
Overview: Train from Brookline, MA to Chicago, IL
Trains from Brookline, MA to Chicago, IL run on average 1 times per day, taking around 21h 15m. Cheap train tickets for this journey start at $295 (€239) if you book in advance.
There are 1 trains per day. The earliest train runs at 12:57, the last at 12:57. The fastest train covers the 846 miles (1363 km) distance in 21h 15m.
Distance 846 miles (1363 km) |
Average train duration 21h 15m |
Cheapest ticket price $295 (€239) |
Trains per day 1 |
Direct trains 1 |
Fastest train 21h 15m |
First train 12:57 |
Last train 12:57 |
Train companies: Amtrak from Brookline, MA to Chicago, IL trainsAmtrak trains will get you between Brookline, MA and Chicago, IL from $295 (€239). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Brookline, MA to Chicago, IL
Find answers to the most common questions about traveling from Brookline, MA to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

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