
Buses from Chicago, IL to Windham, NY travel the 1084mi (1744.52km) journey, taking approximately 1d, 5h, 52m. Usually, there are 24 buses operating per day. While the average ticket price for this journey is around $265.57, you can find the cheapest bus tickets for as low as $117.10.
Windham, NY 12496
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.






Welcome to Windham, NY, a charming Catskill town that promises a refreshing escape from the daily grind. Nestled in stunning natural beauty, Windham offers year-round adventures for outdoor enthusiasts and serenity seekers alike. In the warmer months, explore an extensive network of hiking and biking trails that cater to all skill levels. For those leading a descent down rather than up, the Windham Mountain Bike Park is the place to be. When winter rolls around, hit the slopes at Windham Mountain Resort for some stellar skiing and snowboarding.
Art lovers should swing by the local galleries where rustic charm meets artistic flair. Feeling peckish? The town boasts cozy eateries serving delightful home-cooked meals that make you feel right at home. And let's not forget to raise a glass at one of the local breweries or vineyards.
Whether you hop on a bus to Windham for adventure or relaxation, you're sure to find an oasis that's as lively or laid-back as you wish.
How long does it take to get from Chicago to Windham?
How many buses are there from Chicago to Windham?
How early should I arrive at Chicago?
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?