Discover the stunning landscapes and rich culture of Illinois, where rolling prairies, historic cities, and vibrant communities create unforgettable experiences. From the bustling streets of Chicago to the charming small towns of the Midwest, every corner of Illinois offers something special—whether it’s scenic drives, cultural landmarks, or outdoor adventures. Explore the natural beauty of the Illinois River, the historic sites of Springfield, or the scenic trails of the Shawnee National Forest. Immerse yourself in the state’s deep-rooted heritage, from Native American history to the architectural wonders of the Prairie School style. Whether you’re seeking adventure, history, or quiet moments in nature, Illinois delivers the perfect blend of bold spirit and timeless charm.
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago…
Discover many of Chicago's best-known landmarks—and explore without breaking a sweat—on this private electric bike tour. Meet your guide right at the Buckingham Fountain, grab your e-bike and helmet, and get ready to explore. You'll view Lakefront landmarks like the…
Admire up-close views of the Chicago skyline—and a fireworks show over the city—on this tiki bar boat tour. In the evening, make your own way to the departure point at the Chicago Riverwalk, hop aboard, and get comfortable in the…
Leave behind the stuffy, slow-moving tour groups and explore Chicago’s Millennium Park on your own—but with a guide in your pocket. Using just your smartphone, pausing as you like, you’ll learn all about “The Bean,” Lurie Garden, Crown Fountain, and…
When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50…
On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city…
Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the…
Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and…
Join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer! Chase your Monday BLUES away aboard the 148 foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied…
Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour…
Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic…
Learn firsthand about Black History from a 5th generation South Sider in a 2.5-hour walking tour of Bronzeville and beyond. Highlights of the tour include, Barack Obama’s home, Muhammad Ali’s home, Local murals and street art and Drinks! The tour…
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