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Trailways Bus Tickets
from Brookline, MA to Chicago, IL

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Overview

About buses from Brookline, MA to Chicago, IL

Buses from Brookline, MA to Chicago, IL travel the 854mi (1374.38km) journey, taking approximately 1d, 10h. Usually, there are 4 buses operating per day. While the average ticket price for this journey is around $346.78, you can find the cheapest bus tickets for as low as $330.93.

  • Distance
    854mi (1374.38km)
  • Average trip duration
  • Average bus ticket price
    $346.78
  • Trips per day
    4
  • Top Carriers
    FlixBus

Bus Station Information for Chicago, IL

Chicago (95th & Dan Ryan)

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Chicago, IL 60628

Curbside Stop
Address
95th & Dan Ryan 
Chicago, IL 60628
Phone Number
(800) 858-8555
More Detailsabout Chicago (95th & Dan Ryan) Curbside Stop

Chicago (Cumberland Avenue)

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Chicago, IL 60631

Curbside Stop
Address
5800 N Cumberland Ave 
Chicago, IL 60631
Phone Number
(800) 858-8555
More Detailsabout Chicago (Cumberland Avenue) Curbside Stop

Chicago (Bus Station)

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Chicago, IL 60607

24 Hours
Bus Station
Address
630 West Harrison Street 
Chicago, IL 60607
Phone Number
(800) 858-8555
More Detailsabout Chicago (Bus Station) Bus Station

Chicago (Amtrak Union Station)

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Chicago, IL 60606

Curbside Stop
Address
225 S. Canal St. 
Chicago, IL 60606
Phone Number
(800) 858-8555
More Detailsabout Chicago (Amtrak Union Station) Curbside Stop

City InformationforBrookline, MA

Thinking about a quaint New England escape? Brookline, MA, is calling your name. Just a stone's throw from Boston, this charming town brims with history, culture, and a unique local spirit that makes it worth the trip.

Start your adventure at the John F. Kennedy National Historic Site, where the storied past of a beloved president comes to life. If the arts are your passion, Brookline Booksmith offers a literary haven, along with an endless selection of titles to pique your interest. Your inner cinephile will rejoice at the Coolidge Corner Theatre, a treasured hub for independent films with a touch of vintage flair.

As you roam the streets, the vibrant hum of local cafes and eclectic eateries provides the perfect backdrop. Ethnic flavors blend seamlessly with classic New England charm, promising a feast for every palate.

So why wait? Book a bus to Brookline, MA, and immerse yourself in this delightful town that promises both discovery and charm around every corner. Secure your spot on a Trailways bus and let the adventure begin!

City InformationforChicago, IL

There’s so much to see in the Windy City, you’ll be booking your next bus to Chicago before your trip is over. No matter the season, there’s plenty to do, from lounging on lakeside beaches in the summer to ice skating in Millennium Park.

Chicago’s famous for its dogs and its deep dish, if you’re looking for eats. Museums dot the map, including The Art Institute of Chicago, Field Museum, and Griffin Museum of Science and Industry. Catch a game if your sport’s in season – Bulls or Bears, Cubs or White Sox.

If you ask a local – which we always do – an Architecture Tour is on the don’t miss list. And if you’re on a budget, just go for a stroll on the Riverwalk, Navy Pier, or by “the bean” - Millennium Park’s famed Cloud Gate sculpture.

Whatever mood strikes you, Chi-town's got something to keep you busy.

Scenic photo of Chicago, ILScenic photo of Chicago, ILScenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL

Frequently Asked Questions about the Bus Ride

Reach Chicago easily by bus from Brookline. Trailways has 4 Chicago-Brookline trips starting at $330.93. Take a convenient and affordable bus trip to Chicago today!