- Must visit
Art Institute Of Chicago
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
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The cheapest and fastest trains from Brookline, MA to Chicago, IL
Showing times and prices for Jun 16
Cheapest price
$456
Average price
$456
Fastest journey
21 h 15 m
Average duration
21 h 15 m
Trains per day
1
Distance
1363 km
Cheap tickets
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 $456 if you buy it on the day, but the cheapest tickets can be found for only $456.
Fast trains
Of the 1 trains that leave Brookline, MA for Chicago, IL on Tue, Jun 16, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Jun 16 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 Tue, Jun 16 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.
12:57 PM21h15Brookline, MA10:12 AMChicago, IL$4561One-way0 transfers
- 12:57 PM21h15Brookline, MA10:12 AMChicago, IL$4561One-way0 transfers
Travel Information
Compare train, bus, and flight for Brookline, MA to Chicago, IL
Omio recommends booking the train 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 $255. For those with little time consider booking a flight which can get you there in 3h 0m. The ticket price range depends on the travel mode: a flight costs an average of $255, and a train costs an average of $880.
Distance: 846 miles (1363 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$880 Average price | $255 Average price Cheapest | $314 Average price | $200 Average price (fuel + tolls) |
26h 55m Average total duration 26h 25m Onboard + 30m Additional time* | 6h 0m Average total duration Fastest 3h 0m Onboard + 3h 0m Additional time* | 34h 45m Average total duration 34h 15m Onboard + 30m Additional time* | 14h 45m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Brookline, MA to Chicago, IL is a flight with an average price of $255 (€207).
This is compared to other travel options from Brookline, MA to Chicago, IL:
A flight is $59 (€47) less than a bus for this route with tickets for a bus from Brookline, MA to Chicago, IL costing on average $314 (€254).
A flight is $625 (€507) less than a train for this route with tickets for a train from Brookline, MA to Chicago, IL costing on average $880 (€714).
The fastest way to travel from Brookline, MA to Chicago, IL is by flight with an average journey time of 3h 0m.
Other travel options to Chicago, IL take longer:
Train takes on average 26h 25m.
Bus takes on average 34h 15m.
It's helpful to compare your options as there are 3 ways to travel between Brookline, MA and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Brookline, MA to Chicago, IL among Omio's users.
Take the train. It's the cheaper option, and the extra time on board is usually more relaxing than driving it.
Tickets start at around $880 (€714) compared to roughly $200 (€162) in fuel and tolls — a saving of about $-679.75 (€-551.39). The journey takes 26h 25m versus 14h 45m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
Live departures
Brookline, MA to Chicago, IL train times
The table below shows live departures for Brookline, MA to Chicago, IL trains for today, Monday, June 15. You can also manually refresh the results below to see updated train journeys.
Last updated at
| 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.
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Journey information
Overview: Train from Brookline, MA to Chicago, IL
USAUSA
Trains from Brookline, MA to Chicago, IL run on average 6 times per day, taking around 26h 25m. Cheap train tickets for this journey start at $880 (€714) but you can travel from only $255 (€207) by flight.
There are 2 trains per day. The earliest train runs at 11:20, the last at 11:20. The fastest train covers the 846 miles (1363 km) distance in 26h 25m.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Flight from $255 (€207)
Distance 846 miles (1363 km) |
Average train duration 26h 25m |
Cheapest ticket price $880 (€714) |
Trains per day 6 |
Direct trains 2 |
Fastest train 26h 25m |
First train 11:20 AM |
Last train 11:20 AM |
Cheapest Month Jan |
Cheapest Day Wed |
High Season Apr - Jun |
Low Season Oct - Dec |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Flight from $255 (€207)
Train companies: Amtrak from Brookline, MA to Chicago, IL trainsAmtrak trains will get you between Brookline, MA and Chicago, IL from $255 (€207). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
About
Amtrak is the main passenger train operator in the United States, providing medium- and long-distance intercity services across 46 states and three Canadian provinces. Operating over 300 trains daily and serving more than 500 destinations, Amtrak connects cities and regions nationwide through routes such as the high-speed Acela in the Northeast Corridor, the scenic Coast Starlight along the West Coast, and the Empire Builder linking Chicago to the Midwest and the Pacific Northwest. Other notable services include the Northeast Regional, Keystone Service, and the unique Auto Train, which allows passengers to bring their cars onboard. Amtrak offers a variety of classes to suit different budgets and travel needs, including Coach, Business, First Class, and Sleeper Class with options like Roomettes, Bedrooms, and Bedroom Suites for overnight journeys. Ticket types include Saver, Value, Flexible, Business, and Premium. Onboard amenities vary by service but may include comfortable seating, Wi-Fi, power outlets, dining options, and lounge access on select trains. Popular routes include Washington, D.C.–Boston, San Diego–San Luis Obispo, San Jose–Sacramento, and Chicago–Seattle.
Luggage & cancellation policy
Average Duration
26h 25m
Cheapest Price
$880 (€714)
Amtrak frequency
6 a day
Luggage included
2 personal items and 2 carry-on bags included free
Luggage storage
Overhead racks, under seats, and designated luggage areas at end of cars
Cancellation Policy
Cancellation policies depend on ticket type and timing
Refund
Full refund if train is canceled by Amtrak
Amenities on board the train
Wifi
Food sold onboard
Café car with snacks, beverages, and light meals. Long-distance trains have full-service dining cars
Seat reservation
Included in ticket price for Business and First Class. Optional fee for Coach Class
Toilets
USB plugs
Accessibility
Wheelchair spaces, accessible restrooms, Red Cap assistance service, accessible platforms and stations
Pets
Small pets under 20 pounds allowed for $26 fee. Must be in carrier. Service animals travel free
Quiet zone
Complete guide to Chicago
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
Major natural history museum known for Sue the T. rex, ancient cultures, and large family-friendly science exhibits.
- Must visit
Museum Of Science And Industry
Large hands-on science museum in Hyde Park with a U-505 submarine, aviation exhibits, and immersive interactive displays.
- Must visit
Millennium Park
Chicago’s signature public space, home to Cloud Gate and major events, with strong appeal for first-time visitors and photographers.
- Must visit
Chicago Riverwalk
Scenic pedestrian route along the Chicago River, popular for architecture views, strolling, and social-media-friendly city scenes.
- Must visit
Magnificent Mile
Famous stretch of North Michigan Avenue known for landmark architecture, flagship stores, and busy big-city energy.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, relish, tomato, pickle spear, sport peppers, and celery salt.
Italian Beef Sandwich
A classic Chicago sandwich of thin-sliced seasoned beef served on a roll, often dipped in jus and topped with giardiniera or sweet peppers.
The Purple Pig
A well-known Magnificent Mile restaurant serving Mediterranean-influenced small plates, charcuterie, and strong wine selections.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for inventive tasting menus and a polished, theatrical experience.
Lou Malnati's Pizzeria
A legendary Chicago pizzeria best known for buttery-crust deep-dish pizza in a casual, family-friendly setting.
United States Dollar
Moderate by U.S. big-city standards. Hotels can be pricey downtown, but food and transit offer good value.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 25-45 per person at a mid-range restaurant.
- Fine dining
- USD 80+ per person before drinks and tip.
- Coffee
- USD 4-7 for a regular café coffee.
Tipping culture
Tip 18-20% at sit-down restaurants; 20%+ for great service. USD 1-2 per drink at bars, round up or 10-15% for taxis, and USD 1-2 per bag for hotel staff.
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.
Train ticket prices from Brookline, MA to Chicago, IL can vary. The cheapest ticket starts at $880 (€714), while the average price is around $880 (€714).
The train from Brookline, MA to Chicago, IL takes 26h 25m and runs 6 per day.
The first train from Brookline, MA to Chicago, IL leaves at 11:20 AM.
The distance by train from Brookline, MA to Chicago, IL is 846 miles (1363 km).
The last train from Brookline, MA to Chicago, IL leaves at 11:20 AM.
There is no high speed train available from Brookline, MA to Chicago, IL.
Yes, there is a direct train from Brookline, MA to Chicago, IL. This service operates 2 times per day, provided by Amtrak.
Unfortunately, there is no night train available from Brookline, MA to Chicago, IL.
The train station in Brookline, MA that goes to Chicago, IL is South Station, Boston, MA, which connects to Chicago Union Station, Chicago, IL.
The cheapest way to get from Brookline, MA to Chicago, IL is by flight, with a cost of around $255 (€207).
The train journey from Brookline, MA to Chicago, IL offers a mix of urban and rural scenery, featuring picturesque views of New England landscapes, green forests, and stretches of the Midwest. However, it is not typically highlighted as one of the most scenic routes in the U.S.
A day trip from Brookline, MA to Chicago, IL is not feasible, as the journey takes 26h 25m and covers 846 miles (1363 km). The frequency is 1 per day for trains.
In Chicago, IL, you can explore the Museum of Science and Industry and its interactive exhibits, enjoy the vibrant neighborhoods like Wicker Park and Lincoln Park, take a river cruise to view iconic architecture, and attend a live performance at the historic Chicago Theatre. Visit Lincoln Park Zoo for a free and enjoyable day. For sights, don't miss Millennium Park with its modern art, the renowned Art Institute of Chicago, the entertainment hub of Navy Pier, panoramic views from Willis Tower Skydeck, and the fascinating exhibits at the Field Museum.
To fully experience Chicago, IL, plan for at least 3-4 days to visit key attractions such as Millennium Park, The Art Institute of Chicago, Navy Pier, and explore diverse neighborhoods.
Yes, you can take the train from Brookline, MA to Chicago, IL.
Since neither Brookline, MA nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
Popular day trips by train from Chicago, IL include Milwaukee, WI, South Bend, IN, New Buffalo, MI, Racine, WI, Elkhart, IN.
We recommend using the train as it is the most popular way to get from Brookline, MA to Chicago, IL among Omio's users.
Items not allowed on trains typically include hazardous materials such as explosives, flammable liquids, corrosive substances, and illegal drugs. Additionally, large or bulky items that may obstruct aisles or emergency exits, as well as pets without proper carriers, may be restricted. Specific prohibited items can vary by train operator and region, so please check the rules for your particular journey.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular train stations
Popular train stations from Brookline, MA to Chicago, IL
Brookline
Chicago
Amenities at train station
Wifi
Lockers
Parking
Dining
ATM
Taxis
Accessibility
WC
Hotel
Lounge
Lost and Found Office
Ticket Office
Bike Parking
Car Rental
Information Desk
Luggage Cartsinformation
Ticket Office Hours
- 5:00 AM - 12:00 AM Monday - Sunday
Distance to city center
3 km
Number of platforms
24Wifi
- Free
Parking
- 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.
Dining
- The Chicago Firehouse Restaurant
- Lou Mitchell's
Taxis
- Outside the main entrance.
Accessibility
- Elevators, ramps, restrooms.
WC
- $1
Hotel
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
Lounge
- Located in the main hall
Lost and Found Office
- Located in the main hall
Car Rental
- Avis
- Budget
- Enterprise
Information Desk
- Located in the main hall
Luggage Carts
- Free
Station Plan
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
Public transit options for Union Station
- Bus: Several lines available
- CTA: Blue Line, Pink Line
More options for your journey from Brookline, MA to Chicago, IL
Here are some other resources that might have the information you need
Most popular trains to and from Chicago, IL and Brookline, MA
Most popular train connections to Chicago, IL
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