
Buses from Stroudsburg, PA to Chicago, IL travel the 1633mi (2628.05km) journey, taking approximately 1d, 22h, 40m. Usually, there is 1 bus operating per day. While the average ticket price for this journey is around $398, you can find the cheapest bus tickets for as low as $398.
Chicago, IL 60628
Chicago, IL 60631
Chicago, IL 60607
Chicago, IL 60606
Feel like stepping into America’s quaint charm on your next journey? Hop on a bus to Stroudsburg, PA, and uncover this delightful town nestled in the heart of the Pocono Mountains. With its rich blend of natural beauty and small-town warmth, Stroudsburg welcomes travelers seeking a memorable escape.
Start your exploration at the Sherman Theater, famous for live performances ranging from local talents to big-name acts. Art lovers will appreciate the town’s creative streak at the Andrei Art Gallery, featuring works from both regional and international artists. For a walk on the wild side, the nearby Delaware Water Gap offers hiking trails with breathtaking views and outdoor adventures for every skill level.
As you wander downtown, you’ll find boutique shops and cozy cafés that make Stroudsburg’s streets feel like a home away from home. Foodies, your taste buds are in for a treat with a variety of delicious dining options, from American classics to international delights. So buckle up and let the Trailways bus ride lead you to the charms of Stroudsburg, PA. Your next adventure is just a ticket away!


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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