The cheapest and fastest trains from Brookline, MA to Chicago, IL
Cheapest price
$171
Average price
$171
Fastest journey
22 h 15 m
Average duration
22 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 $171 if you buy it on the day, but the cheapest tickets can be found for only $171.
Of the 1 trains that leave Brookline, MA for Chicago, IL on Wed, Apr 29, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, Apr 29 the direct trains cover the 1363 km distance in an average of 22 h 15 m but if you time it right, some trains will get you there in just 22 h 15 m .
On Wed, Apr 29 the slowest trains will take 22 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.
5:57 PM22h15Brookline, MA4:12 PMChicago, IL$1711One-way0 transfers
5:57 PM22h15Brookline, MA4:12 PMChicago, IL$1711One-way0 transfers
Travel Information
Compare train, bus, and flight for Brookline, MA to Chicago, IL
Omio recommends booking the flight 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 $84. 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 $84, and a train costs an average of $171.
Distance: 846 miles (1363 km)
Compare train with
| Train | Most popular Flight | Bus |
|---|---|---|
$171 Average price | $84 Average price Cheapest | $152 Average price |
22h 45m Average total duration 22h 15m Onboard + 30m Additional time* | 6h 5m Average total duration Fastest 3h 5m Onboard + 3h 0m Additional time* | 36h 35m Average total duration 36h 5m Onboard + 30m 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 tomorrow, Wednesday, April 29. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 5:57 PM Brookline, MA | 22h15 | 4:12 PM 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.
Apr 29
Apr 30
May 01
May 02
May 03
May 04
May 05
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 $171 (€137) but you can travel from only $84 (€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 $171 (€137) |
Trains per day 5 |
Direct trains 2 |
Fastest train 22h 15m |
First train 5:57 PM |
Last train 5:57 PM |
Cheapest Month Jan |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Oct - Dec |
Train companies: Amtrak from Brookline, MA to Chicago, IL trainsAmtrak trains will get you between Brookline, MA and Chicago, IL from $84 (€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.

popular train stations
Popular train stations from Brookline, MA to Chicago, IL
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
More options for your journey from Brookline, MA to Chicago, IL
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