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Trailways Bus Tickets
from Bennington, VT to Chicago, IL

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Overview

About buses from Bennington, VT to Chicago, IL

Buses from Bennington, VT to Chicago, IL travel the 748mi (1203.79km) journey, taking approximately 1d, 3h, 13m. Usually, there are 3 buses operating per day. While the average ticket price for this journey is around $192.17, you can find the cheapest bus tickets for as low as $144.20.

  • Distance
    748mi (1203.79km)
  • Average trip duration
  • Average bus ticket price
    $192.17
  • Trips per day
    3
  • Top Carriers
    Vermont Translines

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 InformationforBennington, VT

Get ready for a cozy escape in Bennington, VT, where small-town charm meets scenic beauty. Your bus to Bennington delivers you to a town bursting with history and culture. First things first: stroll through the quintessentially quaint downtown, where antique shops and local boutiques invite you in with open doors. Art lovers, the Bennington Museum awaits, showcasing masterpieces from regional artists and the vibrant history of southwestern Vermont.

Outdoor enthusiasts will find solace in the serene landscapes of the Green Mountains. Hiking? Exploring Mount Anthony or wandering through the serene paths of the nearby Appalachian Trail should be high on your list. If history calls, make your way to the iconic Bennington Battle Monument, standing tall with panoramic views waiting as your reward for climbing up.

Your taste buds won't be left out either. Local eateries whip up everything from hearty comfort food to delectable Vermont maple treats. Ready to savor the simple joys of New England life? Hop on that bus to Bennington, VT, 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

Need information on buses from Bennington to Chicago? You can take one of our 3 daily trips from Bennington to Chicago for prices starting from $144.20. Purchase Chicago bus tickets now.