There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internatio... More

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing buildings in chronological order, from early skyscrapers to new sup... More

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the orig... More

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Wi... More

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor. Biking is ... More

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider stories behind the city’s rich food culture.... More

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and insights about the city’s architecture, neighbo... More

Discover the fascinating history of Chicago from a whole new perspective — on the water! This 120-minute Guided History Tour along the Chicago River brings the city’s past to life through captivating stories, iconic landmarks,... More

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who shares local stories, history, and insights while guiding you through t... More

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable experience, customizable from 2 to 8 hours. From the iconic skyline to ... More

Shoreline water taxis are the fast and fun way to get to Chicago’s top attractions. Our water taxis aren’t tours, but they are a great way to get around town. Offering multiple docks conveniently located near major attractions... More

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a... More

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think of the future. The gleaming materials, the perfect precision of the details… it’s the epit... More

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our floating Tiki Bar, Island Time! Cruise along the scenic Chicago R... More

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest running city bike tour company, who recently ranked as Top 20 Food Tours in the ... More

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic stops ✔️ Zero wasted time ✔️ Only the best views, landma... More

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop... More

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views as well as views of Chicago's world-famous skyline and graceful lakef... More

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the wo... More