
Buses from Woodstock, NY to Chicago, IL travel the 0mi (0.00km) journey, taking approximately 1d, 6h, 21m. Usually, there are 20 buses operating per day. While the average ticket price for this journey is around $254.56, you can find the cheapest bus tickets for as low as $253.44.
Chicago, IL 60628
Chicago, IL 60631
Chicago, IL 60607
Chicago, IL 60606
Set your sights on Woodstock, NY, where the laid-back vibe and artistic flair create a unique retreat from the hustle and bustle. Known as a haven for creatives and music lovers, this charming town offers more than its famous festival name. As you plan your trip, consider catching a bus to Woodstock—it's the perfect start to discovering this vibrant community.
Stroll down Tinker Street, lined with quaint shops and art galleries that showcase local talent. Feel the creative energy as you navigate through colorful corners and handcrafted treasures. The town is a live music hotspot, reflecting its legendary history, so grab a coffee and enjoy some tunes. Outdoor enthusiasts will relish a hike in the Catskills, with stunning trails ready to be explored.
Expect delightful dining options, ranging from cozy cafes to farm-to-table eateries, making each meal a memorable experience. Whether you're there for the art, the music, or just to relax, Woodstock promises an unforgettable mix of culture and nature, all wrapped up in those picturesque mountain views.






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.






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