
Buses from Middlebury, VT to Chicago, IL travel the 753mi (1211.83km) journey, taking approximately 1d, 6h, 28m. Usually, there are 2 buses operating per day. While the average ticket price for this journey is around $164, you can find the cheapest bus tickets for as low as $164.
Chicago, IL 60628
Chicago, IL 60631
Chicago, IL 60607
Chicago, IL 60606
Hop on a bus to Middlebury, VT, and get ready to savor the charm of this quintessential New England town. Nestled amid the Green Mountains, Middlebury is a delightful blend of scenic beauty and a vibrant community spirit. Start your adventure with a walk around the historic downtown, where 19th-century architecture and inviting local shops set the scene. History enthusiasts will love the Henry Sheldon Museum, the oldest community museum in the nation, boasting a rich collection of Vermont artifacts.
If you’re a nature lover, head to nearby Middlebury College Snow Bowl for year-round outdoor activities, from skiing in the winter months to unbeatable hiking and views in the warmer seasons. Beer connoisseurs won't want to miss a stop at Otter Creek Brewing for a taste of local craft brews, perfect after a day of exploring.
Middlebury’s charm lies in its welcoming essence and abundance of things to do, making it a perfect getaway that’s only a comfortable bus ride away. So why not plan your next escape to this delightful destination?
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.






How long does it take to get from Middlebury to Chicago?
How many buses are there from Middlebury to Chicago?
How early should I arrive at Middlebury?
What is the average cost of the trip?
What bus companies offer services?
How long does it take?
What if my question isn't listed?