Walking Chicago rewards curious travelers with deep insights into America’s great Midwestern metropolis. The most worthwhile tours focus on three main themes: architecture tours highlighting the city’s world-famous skyline and historic buildings, mob-themed walks exploring the fascinating Al Capone era, and food tours sampling Chicago classics like deep-dish pizza and Italian beef.
We especially love the Architecture Foundation’s downtown tours for their expertly trained docents and comprehensive coverage of the Loop’s architectural treasures.
For spine-tingling fun, the evening ghost tours through River North deliver just the right mix of history and haunted tales.
Food-wise, you can’t beat the West Loop tasting tours for their behind-the-scenes access to the city’s hottest restaurant district.
Let’s explore the top walking tours that showcase Chicago at its authentic best.
Key Points
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The Chicago Favorites Ultimate Food and Walking Tour offers a 3-hour experience showcasing classic Chicago dishes like deep-dish pizza and Italian beef sandwiches.
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The Chicago Architecture Walking Tour: Dazzling Interiors provides a 100% recommended experience highlighting the city’s iconic buildings and hidden architectural gems.
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The Chicago Walking Tour: Historic Treasures of Chicago focuses on renowned architecture across Michigan Avenue and the Loop, with a group size limited to 15.
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The Gangsters and Ghosts Walking Tour is a 94% recommended 2.5-hour exploration of the Loop, Millennium Park, and the Chicago Theatre.
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Customized private walking tours, such as the Chicago Walking Tour of West Town, offer a 5.0-rated personalized experience tailored to individual interests.
Chicago: Gangsters and Ghosts Walking Tour
Often praised by travelers, the Chicago: Gangsters and Ghosts Walking Tour takes visitors on a captivating journey through the city’s dark and thrilling past.
With a near-perfect 94% recommendation rate, this walking tour is a must-do for those interested in Chicago’s notorious gangsters and haunting ghost stories.
Led by engaging guides who share personal anecdotes, the tour covers major landmarks and hidden corners, including the Loop, Millennium Park, and the iconic Chicago Theatre.
Clocking in at 2.5 hours, the experience offers the right balance of historical insights and interactive storytelling.
Whether you opt for the walking tour or an immersive bus experience, this tour is an excellent way to uncover Chicago’s tangled underworld.
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Chicago Favorites Ultimate Food and Walking Tour
Immerse yourself on the Chicago Favorites Ultimate Food and Walking Tour, where you’ll embark on a culinary and historical adventure through the heart of the Windy City.
Over 3 hours and 1.5 miles, you’ll visit iconic landmarks like Millennium Park and the Magnificent Mile, while savoring deep-dish pizza, Italian beef sandwiches, and more.
With a maximum group size of 16, you’ll enjoy personalized attention from your expert guide, who’ll share insider tips and stories.
The tour’s generous food tastings, optional beer sampling, and complimentary bike/kayak rental make it a comprehensive and value-packed experience.
Accommodating dietary needs, this tour is perfect for those seeking to discover Chicago’s rich food culture and sights.
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
Stepping into the heart of Chicago’s Loop, the Chicago Architecture Walking Tour: Dazzling Interiors immerses participants in the captivating world of the city’s architectural marvels.
This highly acclaimed tour, with a 100% traveler recommendation, offers an insider’s perspective on the iconic buildings and hidden gems that define Chicago’s architectural landscape.
Led by knowledgeable and engaging guides, the tour provides a unique educational experience, as visitors learn the context and stories behind the structures.
With a maximum of 20 travelers per group, the tour ensures an intimate and personalized exploration of Chicago’s architectural heritage, making it a must-do for both first-time visitors and long-time residents.
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Chicago in a Day: Food, History and Architecture Walking Tour
This comprehensive Chicago in a Day: Food, History and Architecture Walking Tour provides an enriching exploration of the city’s diverse offerings.
Over 5 hours, travelers embark on a 3-4 mile journey, sampling iconic Chicago deep-dish pizza, Italian beef sandwiches, hot dogs, and popcorn.
A knowledgeable local guide shares insights into the city’s architecture and history, leading the small group of up to 12 people.
With overwhelmingly positive reviews, this tour accommodates wheelchair users and children under 6 for free.
Travelers consistently praise the guide’s expertise and the memorable combination of food and sightseeing, making this an exceptional way to experience the heart of Chicago.
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Chicago Walking Tour: Historic Treasures of Chicago
Travelers exploring Chicago’s historic treasures embark on an engaging walking tour that showcases the city’s renowned architecture.
The “Chicago Walking Tour: Historic Treasures of Chicago” takes visitors on a captivating journey through the city’s iconic Michigan Avenue, State Street, and Loop districts.
Led by knowledgeable and passionate guides, the tour offers a deep dive into the city’s art deco interiors, including the stunning Palmer House Hotel and the Chicago Cultural Center.
With a maximum of 15 travelers, the small-group format allows for an intimate and personalized experience.
Praised for its informative content and engaging guides, this tour is accessible, flexible, and delivers exceptional value, making it a must-do for both visitors and locals interested in Chicago’s architectural heritage.
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Chicagos Chinatown Food and Walking Tour
Visitors to Chicago can often be found exploring the vibrant and flavorful Chinatown neighborhood on a guided food and walking tour.
The Chicago Chinatown Food and Walking Tour is a highly-recommended 2-hour experience that showcases the area’s diverse cuisine and culture. For $79.99, participants can enjoy a delectable lineup of signature dishes like dim sum dumplings, Szechuan hot pot, and custard tarts, all while strolling through Chinatown Square and learning from knowledgeable guides.
The tour accommodates dietary restrictions and offers a VIP upgrade with alcoholic beverages. With 98% positive reviews and a Badge of Excellence, this immersive culinary adventure is a must for anyone seeking an authentic taste of Chicago’s thriving Chinatown.
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Chicago Walking Food Tour With Secret Food Tours
Embarking on a culinary exploration of Chicago’s vibrant food scene, the Chicago Walking Food Tour by Secret Food Tours offers an immersive experience that delights the senses.
With a 98% traveler recommendation and a Badge of Excellence, the tour showcases the city’s diverse immigrant influences through classic dishes like deep-dish pizza, Italian beef sandwiches, and the iconic Chicago-style hot dog.
Led by knowledgeable guides, the small-group experience also includes architectural highlights and historical insights.
Ending at the iconic Millennium Park, the tour provides a well-rounded introduction to Chicago’s rich food and cultural heritage.
Whether seeking a private or group outing, this tour promises an unforgettable taste of the Windy City.
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Chicago Gangster and Food Walking Tour
The Chicago Gangster and Food Walking Tour provides an immersive exploration of the city’s notorious criminal past intertwined with its vibrant culinary scene.
Travelers embark on a 3-hour journey, indulging in three iconic local dishes – Chicago-style steak, hot dogs, and deep-dish pizza – while learning about the city’s gangster history.
Praised for its engaging storytelling and knowledgeable guides, the tour boasts a 96% recommendation rate.
With a maximum group size of 15, participants enjoy a personalized experience.
While the food generally receives positive reviews, some items like the steak and pizza receive mixed feedback.
The tour is family-friendly and accessible, making it a well-rounded option for those seeking to discover Chicago’s unique blend of history and gastronomy.
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Downtown Chicago Walking Pizza Tour
For those seeking to enjoy Chicago’s vibrant pizza culture, the Downtown Chicago Walking Pizza Tour offers an unparalleled opportunity.
This small-group walking tour takes visitors through the Loop and River North neighborhoods, showcasing a variety of pizza styles, from deep-dish to Neapolitan and artisanal.
With a 100% recommendation rate and a Badge of Excellence, the tour provides personalized attention from knowledgeable guides, ensuring a memorable experience.
Travelers can expect generous portions, informative insights into Chicago’s culinary history, and the chance to sample the city’s diverse pizza offerings.
Whether a food enthusiast or new to the scene, this tour is an excellent way to explore the heart of Chicago’s pizza culture.
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Chicago Walking Tour: A Walk Through Time
Offering a captivating journey through Chicago’s architectural marvels, the “Chicago Walking Tour: A Walk Through Time” invites travelers to enjoy the city’s rich history.
With a 98% traveler recommendation and a Badge of Excellence, this tour promises an engaging experience. Led by knowledgeable and personable guides, you will explore the city’s renowned architecture while learning fascinating historical facts.
The tour includes admission to the Galleries of the Chicago Architecture Center and convenient amenities like luggage storage and coat check.
Whether you’re a first-time visitor or a local seeking a fresh perspective, this walking tour is an excellent way to discover the essence of Chicago.
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Chicago Mobs and Haunts Walking Tour
Immersing visitors in Chicago’s captivating underworld, the Chicago Mobs and Haunts Walking Tour takes participants on a gripping journey through the city’s checkered past. Rated 4.5 stars with a 93% recommendation, this 2-hour tour explores the haunts and hangouts of notorious gangsters like Al Capone.
Led by engaging guides in recognizable orange hats, groups of up to 20 traverse Chicago’s historic streets, learning about the city’s mob history and paranormal legends. While not accessible for wheelchair users, the tour is a must for those fascinated by Chicago’s dark side.
With a flexible cancellation policy and convenient public transport access, the Chicago Mobs and Haunts Walking Tour offers an unforgettable glimpse into the Windy City’s shadowy past.
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Chicago Walking Tour: Art Deco Skyscrapers Loop
The Chicago Walking Tour: Art Deco Skyscrapers Loop provides visitors with a captivating exploration of the city’s architectural marvels from the 1920s and 1930s.
Awarded the Badge of Excellence by the Chicago Architecture Center, this 2-hour guided tour takes participants on a journey through Downtown Chicago, showcasing stunning Art Deco skyscrapers.
With a maximum group size of 10, travelers can enjoy personalized attention from the professional guide.
Highlights include the Rookery Building, 1 N La Salle St, and the iconic Chicago Board of Trade Building.
Travelers consistently praise the tour’s knowledgeable guides and the opportunity to discover hidden architectural gems.
Whether a first-time visitor or a Chicago enthusiast, this walking tour offers an enriching experience.
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Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
With a focus on customization, the “Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago” offers visitors a unique opportunity to tailor their exploration of the city’s iconic landmarks and hidden gems.
Led by CTPA licensed guides praised for their knowledge and personalization, the tour takes participants on a 2-hour private journey, with the flexibility to adjust the itinerary to their preferences.
Whether it’s admiring the city’s magnificent architecture, discovering its rich history, or indulging in local cuisine, this tour caters to the individual needs of each group, ensuring an unforgettable experience.
With a 100% recommendation rate and 5.0/5 rating, this customized walking tour is a must-do for those seeking an intimate and tailored exploration of Chicago.
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Chicago Walking Tour of West Town
Exploring the vibrant West Town neighborhood, this walking tour offers a captivating glimpse into Chicago’s dynamic history and diverse culture.
With a 5.0 rating from 30 reviews and a Badge of Excellence, the Chicago Walking Tour of West Town is a must for those seeking an engaging and informative experience.
Led by the knowledgeable and enthusiastic guides Henry and Ian, the tour covers the area’s rich architecture, local history, and fascinating U.S. facts.
Suitable for families, friends, and locals alike, the tour provides a moderate level of physical activity and is easily accessible by public transportation.
At just €48.24 per person, this tour is a budget-friendly way to explore the vibrant West Town neighborhood.
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Chicago Art Deco Madness Walking Tour
Discover the vibrant architectural heritage of Chicago’s Loop area on the captivating Chicago Art Deco Madness Walking Tour.
This highly-rated 100% recommended tour focuses on the city’s preserved art deco buildings from the Roaring 20s. Led by an interior designer and historic architecture expert, you’ll explore about seven notable art deco structures and additional highlights in the Financial District and North Michigan Avenue corridor.
The small-group format ensures personalized attention, with a maximum of 10 travelers. Historical photos are available through a free app, and the tour is stroller accessible, though not wheelchair-friendly.
At $45 per person, this tour offers excellent value and high customer satisfaction.
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Chicago Walking Tour: Historic Skyscrapers
The Chicago Walking Tour: Historic Skyscrapers offers an immersive exploration of the city’s architectural legacy, guiding visitors through its most iconic high-rise buildings.
With a badge of excellence and a 97% recommendation rate, this tour showcases the Fine Arts Building, Auditorium Building, Rookery Building, and other renowned structures.
Participants will enjoy engaging commentary from knowledgeable guides, as well as access to the Galleries of the Chicago Architecture Center.
The small group size and wheelchair accessibility make this tour an excellent choice for architecture enthusiasts.
While some reviewers found the pace slightly rushed, the consensus is that this tour provides a comprehensive and captivating experience.
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Chicago Architecture Walking Tour: Whats New
For those interested in experiencing Chicago’s cutting-edge architecture, the Chicago Architecture Walking Tour: What’s New offers an exciting opportunity.
Led by professional and certified guides, this virtual tour showcases the city’s diverse architectural styles, including early 20th-century, art deco, and mid-century modern, as well as structures built in the last 20 years.
Participants can explore these architectural movements, including brutalism and modernism, in an intimate group of up to 15 travelers.
The tour also includes admission to the Galleries of the Chicago Architecture Center, providing a comprehensive understanding of the city’s architectural landscape.
With convenient meeting and booking options, this walking tour is a must-try for architecture enthusiasts visiting Chicago.
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Chicago Private Walking Food Tour With Secret Food Tours
An exciting opportunity for foodies visiting Chicago is the Chicago Private Walking Food Tour With Secret Food Tours. This 100% traveler-recommended tour provides a personalized introduction to the city’s dynamic dining scene.
Guests can expect to sample a variety of local specialties, including deep-dish pizza, gourmet popcorn, and the iconic Chicago-style hot dog. The tour also includes insights into Chicago’s architecture, history, and culture.
With hotel pick-up and drop-off, as well as gratuity included, this tour offers a convenient and immersive culinary experience. Priced from $306 per person, the tour can be booked with free cancellation up to 24 hours in advance, making it a flexible option for visitors.
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Windy City Ghosts: Hauntings of Chicago Walking Tour
Windy City Ghosts: Hauntings of Chicago Walking Tour offers ghost enthusiasts a spellbinding journey through Lincoln Park’s shadowy past.
This highly-rated tour provides an opportunity to uncover the city’s haunted history, from chilling tales of gangsters and bootleggers to encounters with restless spirits.
With a maximum group size of 15, guests can expect an intimate experience led by professional guides who share intensely researched true stories and documented accounts of paranormal activity.
The tour’s accessible routes and flexible cancellation policy make it an appealing choice for those seeking a unique and accessible urban adventure.
Whether you’re a true believer or just curious, this walking tour promises an unforgettable glimpse into Chicago’s ghostly underworld.
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Downtown Chicago TV and Movie Sites Guided Walking Tour
Embarking on a captivating journey through Chicago’s cinematic landscape, the Downtown Chicago TV and Movie Sites Guided Walking Tour whisks guests away to the iconic filming locations that have graced the silver screen.
With a $36 price tag and a maximum group size of 35, the 5- to 20-minute walking tours between sites allow visitors to explore the Windy City’s on-screen hotspots.
While most travelers can participate, the tour isn’t wheelchair accessible. Reviewers praise the knowledgeable guide and the historical insights, though some note issues with communication regarding changes and the guide’s focus on personal anecdotes.
The tour starts at the Roosevelt University Auditorium Building and ends at Union Station, with confirmation and free cancellation available.
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Recap
Chicago offers a diverse range of walking tours that showcase the city’s rich history, architecture, and culinary delights. Whether you’re interested in learning about the city’s infamous gangsters, indulging in its famous food, or marveling at its stunning buildings, there’s a tour to suit your interests. With so many options, visitors can easily find a walking tour that will provide an unforgettable and immersive experience in the Windy City.