
Buses from Chicago, IL to Bennington, VT travel the 748mi (1203.79km) journey, taking approximately 1d, 6h, 40m. Usually, there is 1 bus operating per day. While the average ticket price for this journey is around $167.51, you can find the cheapest bus tickets for as low as $167.51.
Bennington, VT 05201
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.






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.
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