Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, where you can enjoy free time to stroll, have lunch, or even take a cable ... More

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see landmarks such as the Gold Pyramid House and the stunning Bahāʾī t... More

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour circles Wicker Park, showcasing stunning Victorian mansions o... More

Explore the underground drinking culture of Chicago during the Prohibition era on this captivating app-guided walking tour. Uncover the secrets of hidden bars and speakeasies while learning about the city's notorious figures like ... More

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at every stop, while taking in the captivating sights of the Windy City. Wh... More

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while l... More

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes. Learn more about the art of styling your body features and ta... More

Walk where a nation was born and experience the story behind America’s fight for independence. Join Rosotravel for a 2.5-hour guided walk along the Freedom Trail, crafted for travelers who want insight, emotion, and connection�... More

This unique tour will give you a complete overview of Chicago's architecture. While listening to the history of the city, you will see, in chronological order, some of its oldest buildings, as well as ultra-high towers of recent c... More

Skip the crowds this is a private tour for your group only! Embark on a family adventure starting at the iconic metal horse sculpture at 425 S. Financial Place, a symbol of strength in the city's bustling financial district. Wande... More

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellence, resilience, and activi... More

Enjoy a private, fully personalized sunset tour along Chicago’s scenic lakefront. Travel in comfort with your English-speaking driver, who shares insights into the city’s architecture, skyline, and history while guiding you to... More

This tour offers a refreshing blend of Chicago’s iconic sights and hidden suburban gems, giving travelers a unique perspective on the city's diverse culture, history, and architecture. Start by marveling at Chicago’s world-r... More

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insig... More

Explore Chicago’s vibrant street art and creative neighborhoods on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares insights into the city’s artistic communities, mural cultur... More

Skip the crowds this is a private tour for your group only! Dive into "Chicago's Artsy Cultural Landmarks – Walking Tour," a vibrant exploration of the city's iconic artistic and architectural gems. Start at the Chicago Cultural... 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

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets. ... More

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares in... More

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies you from Chicago to Los Angeles, transforming each stretch of road int... More