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Embark on an unforgettable journey through the Windy City with Free Chicago Walking Tours. Our guided explorations take you through the vibrant tapestry of Chicago’s most iconic neighborhoods and landmarks, unveiling the stories and spectacles that make the city truly unique.
Our meticulously curated tours, lasting approximately 2-hours, cover a distance of just over a mile, ensuring a comfortable pace for all. Spearheaded by seasoned Chicago tour guides, each walk is a blend of entertainment, education, and exploration. Check out our comprehensive TOUR CALENDAR to find and book your next adventure, or delve into the details of each tour by clicking on the images below!
Join us on a thrilling exploration of Chicago’s notorious past with Free Chicago Walking Tours’ Chicago Crime & Gangster Tour. Journey through the rise of the Chicago Mafia, and uncover hidden and famed Mob haunts in the scenic locales of River North and the Loop.
Wind your way through the River North area learning about the multiple gangs and their leaders that were vying for a piece of the prohibition pie. Stops at Marina City Towers and the Lasalle Street Bridge will help explain how all of these characters crossed paths and shaped the future of Chicago.
Chicago Riverwalk & History Tour
A blend of history, architecture, and scenic splendors with our Riverwalk & North Loop Walking Tour, offering a diverse taste of Chicago’s essence. Commencing at Du Sable Bridge, the seed of Chicago’s rich history dating back to the 1670s, we amble along the Chicago River, pausing at iconic sites like Trump International Hotel & Tower, Marina City Towers, and the Heald Square Monument, each narrating unique chapters of Chicago’s tale. The Eastland Disaster tale by the river shores adds a historic poignancy to our expedition.
The tour unfolds Chicago’s artistic flair at Monument with a Standing Beast and the famed Picasso, culminating at the Chicago Cultural Center. Here, the world’s largest Tiffany Glass-domed roof awaits, marking a grand finale to a tour drenched in Chicago’s multifaceted narrative, an experience not to be missed.
NEW FOR 2025 SEASON!
Chicago’s Crown Jewel: Magnificent Mile Tour
Step into Chicago’s golden corridor along North Michigan Avenue, where historic landmarks, luxury shopping, and architectural wonders converge from Lake Michigan to the Chicago River, as our local guide reveals the captivating transformation of the Magnificent Mile and Streeterville from the Great Fire of 1871 to today’s urban grandeur.
NEW FOR 2025 SEASON!
Chicago has long been regarded as on of the top destinations in the world for for architecture enthusiasts. Our Loop & Architecture Tour winds through Chicago’s Loop district giving our guests and up close and personal experience of some of the world’s most influential and gorgeous buildings. Our guide will share the history of Chicago and explain the multiple architectural influences that helped shape Chicago’s incredible skyline.
Our guides have a passion and love for the architecture that makes Chicago so special. Not only will you get a chance to see the beautiful buildings from the outside but the when available the group will be able to check out the insides too – which are sometimes even more impressive! This 2 hour tour is the perfect mixture of Chicago Architecture and history. The tour concludes at the Chicago Cultural Center, just a few steps from the North entrance of Millennium Park.
Immerse in the cradle of American “downtown” in our Chicago Total Loop Walking Tour, encompassing the architectural grandeur, retail history, and the iconic Chicago River. We start at The Sears Tower and learn about “the architectural equivalent of the moon landing”, the innovative design and construction of what would be the tallest building in the world for 25 years.
This unique two-hour, two-mile journey weaves through the heart of Chicago, unveiling the rich history, vibrant public art, and characters that form the essence of the city. From the grandeur of Millennium Park to the stunning display of Chicago’s Picasso, we’ll explore stories etched in stone and time.
Unique Chicago – Off the Grid Tour
Forget stuffy museums or the standard architecture strolls and get lost in the beauty of Chicago’s urban jungle on the new Off the Grid Tour. Hosted by ACME Hotel Company and Free Chicago Walking Tours, the immersive walking tour showcases some of the city’s most Instagrammable spots including Death Alley and the Tiffany Glass Dome at the Chicago Cultural Center, among others.
Chicago Gold Coast Neighborhood Tour
Chicago’s Gold Coast is one of the city’s most iconic neighborhoods. With the shores of Lake Michigan on the east, this is one of the most expensive zip codes in all of Illinois. Nestled among these quiet, tree-lined streets you’ll find elegant multi-million dollar brownstones, numerous historic mansions and some of the wealthiest families in Chicago.
But this area wasn’t always so wealthy. Once upon a time, this was marshland used as burial grounds. The area began to change in 1882 after Potter Palmer, one of Chicago’s business legends, built a castle-like mansion on Lake Shore Drive. Thereafter, Chicago’s wealthy citizens transformed this area into the city’s most exclusive residential enclave.
Millennium Park & Michigan Ave Tour
You will get to see so much of what makes Chicago so special on this tour. The Magnificent Mile, The Chicago River, Millennium Park, Buckingham Fountain and more! Your meeting spot is outside the entrance to on of Chicago’s most beautiful buildings – The Wrigley Building.
From there the group will head south down Michigan Ave learning about some of the folks that helped put Chicago on the map hundreds of years ago. You’ll have incredible photo opportunities of the Chicago River as you make your way to Chicago’s famous Millennium Park.
For larger groups of more than 6, or to book a private, personalized tour, navigate to our PRIVATE TOUR page and complete the contact form. Our private tours offer an intimate, tailored experience, making them perfect for family outings, educational trips, or corporate team-building exercises. With rates starting at a mere $250 for a 2-hour guided tour accommodating up to 20 individuals, Free Chicago Walking Tours offers the most competitive private tour rates in the city.
Discover Chicago from a new perspective, witness its architectural marvels, historical landmarks, and cultural hubs, all while enjoying a leisurely walk. Whether it’s the bustling Magnificent Mile, the historical charm of the Wrigley Building, or the serene beauty of Millennium Park, each tour is a window into the soul of Chicago.
Free Chicago Walking Tours is not just a tour service, it’s your gateway to experiencing Chicago like never before. Reserve your spot today and step into Chicago’s rich tapestry of history, architecture, and culture. Your captivating journey through the heart of Chicago awaits!
