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

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our loop around "Da Loop" we will peel back the layers of this Great Big ... More

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & River North. Compare two American pizzas vs. two Italian pizzas to underst... 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

Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansi... More

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour wi... 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

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

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city... More

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!... More

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and reno... More

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city la... More

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, ... More

Experience the magic of Chicago at dusk on a 90-minute live guided panoramic adventure that captures the city in its most captivating light. Watch the entire skyline come to life, from Magnificent Mile to Museum Campus and beyond.... 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

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. From high up in the sky, you'll be able to take in breathtaking panoramic views of Chicago's iconic skyline, world-famous landmarks,... 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

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how it has shaped the development of buildings within the Loop.... 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

See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't seen Chicago until you have seen it at night while gliding through the park & lakefront on a Segway PT. View Buckingham Fountain's ... More