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Trailways Bus Tickets
from Woodstock, NY to Chicago, IL

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Overview

About buses from Woodstock, NY to Chicago, IL

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.

  • Average bus duration
  • Average bus ticket price
    $254.56
  • Trips per day
    20
  • Top Carriers
    Pine Hill Trailways, Adirondack Trailways

Bus Station Information for Chicago, IL

Chicago (95th & Dan Ryan)

Curbside Stop, use arrow keys or tab to explore more about this bus station

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)

Bus Station, use arrow keys or tab to explore more about this bus station

Chicago, IL 60607

24 Hours
Bus Station
Address
630 West Harrison Street 
Chicago, IL 60607
Phone Number
(319) 753-2864/(800) 858-8555
More Detailsabout Chicago (Bus Station) Bus Station

Chicago (Amtrak Union Station)

Curbside Stop, use arrow keys or tab to explore more about this bus station

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 InformationforWoodstock, NY

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.

Scenic photo of Woodstock, NYScenic photo of Woodstock, NYScenic photo of Woodstock, NY
Scenic photo of Woodstock, NY
Scenic photo of Woodstock, NY
Scenic photo of Woodstock, NY

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

Make your trip from Woodstock to Chicago simple by taking the bus. With 20 bus(es) departing to Chicago daily, our trips average 1 day(s) 6 hour(s) 21 minute(s) and start as low as $253.44. Find your bus ticket to Chicago now.