The cheapest and fastest trains from Brookline, MA to Chicago, IL
Cheapest price
$452
Average price
$452
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 $452 if you buy it on the day, but the cheapest tickets can be found for only $452.
Of the 1 trains that leave Brookline, MA for Chicago, IL on Sun, Mar 15, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Mar 15 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 Sun, Mar 15 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.


Travel Information
Compare train, bus, and flight for Brookline, MA to Chicago, IL
Omio recommends booking the bus as it is the most popular option from Brookline, MA to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $82. For those with little time consider booking a flight which can get you there in 3h 5m. The ticket price range depends on the travel mode: a flight costs an average of $82, and a train costs an average of $168.
Distance: 846 miles (1363 km)
Compare train with
| Train | Most popular Bus | Flight |
|---|---|---|
$168 Average price | $149 Average price | $82 Average price Cheapest |
22h 45m Average total duration 22h 15m Onboard + 30m Additional time* | 36h 35m Average total duration 36h 5m Onboard + 30m Additional time* | 6h 5m Average total duration Fastest 3h 5m Onboard + 3h 0m Additional time* |
Direct Options | Direct Options | Direct Options |
Live departures
Brookline, MA to Chicago, IL train times
The table below shows live departures for Brookline, MA to Chicago, IL trains for today, Saturday, March 14. 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, bus, or flight
Compare train, bus, and flight 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.
Mar 15
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Mar 17
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Mar 21
Journey information
Overview: Train from Brookline, MA to Chicago, IL
Trains from Brookline, MA to Chicago, IL run on average 5 times per day, taking around 22h 15m. Cheap train tickets for this journey start at $168 (€137) but you can travel from only $82 (€67) by flight.
There are 2 trains per day. The earliest train runs at 17:57, the last at 17:57. The fastest train covers the 846 miles (1363 km) distance in 22h 15m.
Distance 846 miles (1363 km) |
Average train duration 22h 15m |
Cheapest ticket price $168 (€137) |
Trains per day 5 |
Direct trains 2 |
Fastest train 22h 15m |
First train 17:57 |
Last train 17:57 |
Train companies: Amtrak from Brookline, MA to Chicago, IL trainsAmtrak trains will get you between Brookline, MA and Chicago, IL from $82 (€67). 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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