Chicago’s walking tours cut right to the heart of what makes this city tick. The best options focus on three main themes: architecture, history, and food. Architecture tours open doors to stunning lobbies and hidden gems, while history walks bring the city’s infamous gangster era to life. Small-group food tours through neighborhoods like West Loop and Wicker Park showcase the local flavors that locals love.
We’re particularly fond of the architecture foundation’s downtown tours for their expertly researched content and the food tours by Chicago Food Planet, which mix neighborhood history with generous tastings. The evening ghost tours deserve special mention – they combine accurate historical information with spine-tingling stories of the city’s darker past.
Let’s explore our favorite Chicago walking tours, ranked by value and experience.
Key Points
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Chicago offers a diverse range of walking tours, including themed experiences like Gangster and Ghost Tours that provide thrilling insights into the city’s dark history.
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Architectural walking tours, such as the Chicago Architecture Walking Tour and the Chicago Walking Tour, allow visitors to explore the city’s iconic buildings and hidden interiors.
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Culinary walking tours, including the Chicago Walking Food Tour and Chinatown Food Tour, offer opportunities to savor local delicacies and gain cultural context behind the city’s vibrant food scene.
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The “Chicago in a Day” tour provides a comprehensive exploration of the city’s food, history, and architecture, covering up to 4 miles and including various food tastings.
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Key features of the walking tours include small group sizes, knowledgeable local guides, and unique perspectives, such as the exploration of the underground Chicago Pedway system.
Chicago: Gangsters and Ghosts Walking Tour
The Chicago: Gangsters and Ghosts Walking Tour immerses visitors in the Windy City’s storied past.
Led by expert guides, the tour explores Chicago’s notorious gangster era and haunted locations. Rated 5.0 stars with a 95% recommendation rate, the 2-3 hour experience is priced starting at $35 per person.
Participants will visit sites like the Palmer House, Congress Hotel, and Death Alley while learning about infamous figures like Al Capone.
The tour also includes walking through the Chicago Loop, Millennium Park, and the Riverwalk.
With a maximum group size of 20, the tour isn’t wheelchair accessible and requires a moderate fitness level.
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Michigan Avenue Rendezvous Walking Tour With Smartphone App
Explore Chicago’s iconic Michigan Avenue like never before with the captivating Michigan Avenue Rendezvous Walking Tour. This 2-hour interactive experience guides participants through the neighborhood’s hidden gems and renowned landmarks using a cutting-edge mobile app.
Set out on a scavenger hunt-style adventure, complete with trivia and challenges that bring the city to life. Covering the Magnificent Mile and Cultural Mile, the tour offers a unique and immersive way to discover Chicago.
Priced at just $15.83 per person with free cancellation up to 24 hours in advance, the tour is suitable for most participants, though not recommended for those with mobility or visual impairments.
Prepare by downloading the Leplace World app and arrive at the meeting point ready to embark on an unforgettable journey.
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
Although designed to captivate architectural enthusiasts, Chicago’s Original Chicago Architecture Interiors Tour appeals to a broader audience seeking a deep dive into the city’s cultural heritage.
Led by knowledgeable local guides, this 93% recommended tour provides access to hidden interiors and exclusive spaces within iconic Loop buildings. With a maximum of 20 travelers, the experience offers a personalized look at Chicago’s architectural preservation and storied past.
Highlights include the striking Chicago Board of Trade building, immersing participants in the city’s rich design legacy.
Conveniently located near public transport, the tour’s small group size and engaging storytelling make it an essential Chicago experience for both first-timers and long-time residents.
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Chicago: Oktoberfest Walking Brewery Tour in Logan Square
This Oktoberfest-inspired walking tour in Chicago’s vibrant Logan Square neighborhood immerses participants in the city’s thriving craft beer scene.
Over the course of 3 hours, groups of up to 10 people will visit three renowned local breweries, learning about the history of Chicago’s brewing industry.
The tour includes exclusive discounts and offerings at each stop, as well as recommendations and insights from a knowledgeable guide.
Guests are encouraged to order drinks and purchase merchandise at their own expense.
The tour is wheelchair accessible and conveniently located near public transportation.
Passport or ID, as well as payment methods, are recommended items to bring.
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Chicago Walking Food Tour With Secret Food Tours
Nestled in the heart of Chicago’s bustling Loop area, the Chicago Walking Food Tour with Secret Food Tours offers visitors a delectable exploration of the city’s iconic culinary landscape.
This highly-rated tour boasts a 98% traveler recommendation, a Badge of Excellence, and a wealth of positive reviews praising the knowledgeable and personable guides.
Participants can indulge in classic Chicago staples like deep-dish pizza, Italian beef sandwiches, and hot dogs, as well as gourmet popcorn, brownies, and a secret dish.
Along the way, the tour showcases the city’s architectural wonders, including the Willis Tower and Millennium Park.
With small-group and private options available, this food-focused adventure is a must-try for any Chicago visitor.
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Chicago: Magnificent Mile Walking Tour
Explore the transformation of Chicago’s iconic Magnificent Mile on this 1.5-hour walking tour.
Discover the area’s architectural evolution, from Parisian and Gothic styles to modern skyscrapers. View landmark buildings like the Tribune Tower and Wrigley Building as you learn about the influence of Daniel Burnham’s Plan of Chicago.
Explore the diverse decor of the Medinah Athletic Club and enjoy admission to the Chicago Architecture Center.
This tour supports the center’s educational initiatives, including programs that inspire the next generation of designers.
With knowledgeable guides and a desire for more coverage, the tour earns an overall rating of 4.7/5 from travelers.
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Chicago Favorites Ultimate Food and Walking Tour
Boasting over 1,393 reviews and a 96% traveler recommendation, the Chicago Favorites Ultimate Food and Walking Tour offers a comprehensive exploration of the city’s iconic culinary and architectural landmarks.
Covering 1.5 miles and suitable for most fitness levels, the tour includes tastes of deep-dish pizza, hot dogs, Italian beef sandwiches, and local craft beer samples.
Visitors will also see major attractions like Millennium Park, the Chicago River, and the Magnificent Mile. Guided by knowledgeable and enthusiastic locals, the experience provides insider tips and stories about Chicago’s history and culture.
With dietary accommodations available, this tour is a must-do for both solo travelers and groups seeking to enjoy the city’s vibrant food scene.
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Lincoln Park Haunted History Walking Ghost Tour
The Lincoln Park Haunted History Walking Ghost Tour offers visitors a chilling exploration of the park’s dark past. Priced at $34.99 per person, the 2.5-hour tour takes participants to key locations, including the Couch Tomb, the Lincoln Park Zoo, and the site of the infamous St. Valentine’s Day Massacre.
Along the way, the knowledgeable live guide shares haunting stories and encourages the use of paranormal equipment to search for spectral evidence.
While the tour has received mixed reviews, with one traveler finding it lacking in content, another praised the guide’s expertise and recommended the experience.
Wheelchair accessible and with free cancellation, this tour promises an immersive ghost-hunting adventure for those brave enough to explore Chicago’s haunted history.
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Chicago in a Day: Food, History and Architecture Walking Tour
This immersive walking tour takes visitors on a comprehensive exploration of Chicago’s rich culinary, historical, and architectural heritage.
Covering up to 4 miles, the half-day experience earned a stellar 98% recommendation rate from over 900 past participants.
Guests enjoy a lineup of 4 classic Chicago food tastings, including deep-dish pizza and a Chicago-style hot dog.
An expert local guide provides in-depth commentary on the city’s landmarks and neighborhoods.
With a maximum group size of 12, the tour offers personalized attention and child-friendly accommodations.
Suitable for all ages and fitness levels, this highly-rated walking tour is a fantastic way to experience the best of Chicago in a single day.
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Ghosts of Old Chicago: River North District Ghost Walk
Setting out on a captivating ghost walk through Chicago’s River North District, visitors uncover the city’s haunting past.
The Ghosts of Old Chicago: River North District Ghost Walk is a 2-hour guided tour rated 4.7 out of 5 stars. For $35, guests explore the neighborhood’s spooky alleyways and historical buildings, learning about the area’s notorious gangsters and ghostly encounters.
Highlights include the infamous Biograph Theater, where notorious gangster John Dillinger met his demise. Participants also visit the site of the St. Valentine’s Day Massacre, delving into the district’s dark history.
This immersive experience provides a unique perspective on Chicago’s shadowy past, perfect for those seeking a thrilling and educational adventure.
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Chicago Walking Tour: Historic Treasures of Chicago
Explore the historic treasures of Chicago’s iconic architecture on the Chicago Walking Tour: Historic Treasures of Chicago.
This highly-rated tour boasts a 99% recommendation rate from 327 travelers. Led by professional and certified guides, the tour focuses on Chicago’s renowned architecture, providing access to the Galleries of the Chicago Architecture Center.
Participants can expect an engaging and educational experience, with reviewers praising the guides’ knowledge, humor, and accommodating nature.
The tour covers a loop from the Chicago Architecture Center to the Chicago Cultural Center, with the option to return with the docent.
Accessible for wheelchair users and stroller-friendly, this tour is a must-do for history and architecture enthusiasts visiting Chicago.
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The Best of Chicago in 2H Walking Tour
Offering a captivating exploration of Chicago’s iconic landmarks, the two-hour “The Best of Chicago in 2H Walking Tour” immerses visitors in the city’s vibrant downtown.
Priced at $40 per person, the tour takes guests through the Loop area, showcasing bold architecture, museums, and renowned attractions like Cloud Gate and the Chicago Theater.
Guided by a local expert, the experience includes a stop at the popular Garrett’s Popcorn and a chance to enjoy a rooftop view of the city and Lake Michigan.
While not suitable for those with mobility impairments, the tour provides a comprehensive introduction to the best of Chicago in a compact timeframe.
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Chicagos Chinatown Food and Walking Tour
For those seeking an immersive culinary and cultural experience in Chicago, the Chicago’s Chinatown Food and Walking Tour provides an unparalleled opportunity.
Rated 5.0 on TripAdvisor and awarded the Traveler’s Choice since 2002, this 2-hour tour takes participants on a journey through Chinatown’s vibrant streets.
Guests will savor a variety of regional Chinese specialties, including dim sum dumplings, spicy meat sandwiches, and Szechuan hot pot, while learning about the cuisine’s cultural influence on the city.
With a maximum group size of 15, the tour offers a personalized experience led by knowledgeable guides.
Whether you’re a food enthusiast or seeking cultural enrichment, this Chinatown adventure is highly recommended.
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Chicago: Small-Group History and Architecture Walking Tour
Tucked away in the heart of the Windy City, the Chicago: Small-Group History and Architecture Walking Tour whisks participants through the city’s vibrant core, unveiling its rich heritage and iconic architectural wonders.
This 2.5-hour excursion, limited to just 10 people, takes guests on a captivating journey that includes stops at the renowned Cloud Gate, the picturesque Chicago Riverwalk, and the bustling Magnificent Mile.
Along the way, an expert guide shares insightful tales about Chicago’s resilient spirit, from the Great Fire to the city’s architectural renaissance.
Offering flexibility with a pay-later option and free cancellation, this tour promises an immersive experience that showcases the best of Chicago’s past and present.
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Chicago Walking Tour: A Walk Through Time
Chicago’s “Chicago Walking Tour: A Walk Through Time” offers visitors an insightful exploration of the city’s rich architectural history.
This express, small-group walking tour covers famous buildings in chronological order, led by a knowledgeable and personable guide. With 163 reviews and a 98% recommendation rate, the tour includes admission to the Chicago Architecture Center’s Galleries, providing an in-depth commentary on the city’s architectural evolution.
Ideal for first-time or time-pressed visitors, the tour’s flexible pacing and accommodation of questions ensure an engaging and informative experience.
The tour’s accessibility, with options for wheelchair, stroller, and public transportation, further enhances its appeal for a wide range of travelers.
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Chicago: West Town Walking Tour
The West Town Walking Tour invites visitors to uncover the vibrant neighborhood’s diverse heritage and burgeoning creative scene.
Exploring the area on foot, guests discover charming historic buildings, trendy boutiques, and innovative street art. The tour showcases the neighborhood’s cultural diversity, from the Polish heritage on Division Street to the thriving Latino community along Milwaukee Avenue.
Along the way, tour-goers can savor local cuisine, from authentic tacos to artisanal coffee. With its blend of old and new, the West Town Walking Tour offers an immersive experience that highlights Chicago’s dynamic urban character.
At 2 hours long, the tour provides an engaging introduction to this vibrant corner of the city.
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Chicago Walking Tour: Art Deco Skyscrapers Loop
Amidst the towering skyscrapers of Chicago’s Loop district, the Art Deco Skyscrapers Loop walking tour invites visitors to uncover the city’s architectural gems from the 1920s and 1930s.
This 2-hour small-group tour, led by a certified guide from the Chicago Architecture Center, explores the iconic Art Deco style through notable landmarks like The Rookery Building and the Chicago Board of Trade Building.
Travelers can expect an engaging and informative experience, with access to hidden building interiors and insider stories.
The tour is highly recommended, with 96% of 128 reviewers praising the knowledgeable guides and unique access to architectural details.
Priced at $30 per person, it’s an excellent choice for architecture enthusiasts and history buffs exploring Chicago.
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Chicago: River North Walking Food Tour
Exploring Chicago’s renowned food scene, the River North Walking Food Tour offers an immersive culinary experience through the neighborhood’s hidden gourmet gems.
Over 3 hours, participants visit 5 acclaimed establishments, sampling specialties like the best doughnut in America, authentic Spanish tapas, and the iconic Chicago deep-dish pizza.
The tour provides insight into food preparation at ethnic eateries and trendy restaurants, while also highlighting the history and culture of the affluent River North area.
With all tastings and bottled water included in the $99 price, the tour delivers excellent value for money.
Reviewers praise the knowledgeable guide and the opportunity to discover Chicago’s vibrant food landscape.
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Chicago Gangster and Food Walking Tour
This Chicago Gangster and Food Walking Tour offers an immersive exploration of the city’s captivating Prohibition-era history and its renowned culinary scene.
With a 5.0-star rating and a 96% recommendation rate from 466 reviews, the tour combines historical insights with tastings of Chicago’s signature dishes, including prime cut steak, hot dogs, and deep-dish pizza.
Guided by experts who bring the city’s gangster past to life, the small-group experience explores River North’s historic hideouts.
Travelers praise the tour’s engaging storytelling, exceptional guides, and diverse food samplings, making it an excellent way to experience Chicago’s captivating blend of culture and cuisine.
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Chicago: History & Architecture Walking Tour W/ Boat Cruise
For those seeking to uncover Chicago’s rich history and architectural marvels, the Chicago: History & Architecture Walking Tour with Boat Cruise offers an immersive experience.
Priced from $104 per person, the 2.5-hour tour covers key landmarks, including Cloud Gate, the Chicago Riverwalk, and the Magnificent Mile. Participants can enjoy a 75-minute Shoreline Architecture Boat Cruise, as well as an optional street food experience.
Led by an English-speaking guide, the small-group tour (limited to 10 participants) provides unique perspectives, such as exploring the underground Chicago Pedway.
With a 3/5 overall rating based on customer feedback, this tour promises an insightful exploration of Chicago’s past and present.
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Frequently Asked Questions
Can I Bring Food or Drinks on the Walking Tours?
Most walking tour companies allow participants to bring food and drinks, but it’s best to check the tour’s policies beforehand. Some may have restrictions or recommendations to ensure an enjoyable and respectful experience for all.
What Happens in Case of Bad Weather?
In case of bad weather, most walking tour providers offer alternative options. They may suggest indoor visits, provide ponchos, or reschedule the tour. Guests should check with the tour company about their policies for inclement weather.
Are the Tours Wheelchair Accessible?
Many walking tours in major cities are wheelchair accessible, allowing all visitors to explore the sights. Tour operators often provide accommodations for those with mobility challenges, ensuring an enjoyable and inclusive experience.
Can I Take Photos During the Tours?
Yes, participants can typically take photos during the tours. Most tour operators encourage guests to capture memorable moments, though they may ask that flash photography be limited to avoid disrupting the experience for others.
How Much Walking Is Involved in Each Tour?
The amount of walking involved in each tour varies, typically ranging from 1-3 miles. Participants should wear comfortable shoes and be prepared for a moderate level of physical activity during the tours. Tour durations and distances can differ, so it’s best to check with the tour operator.
The Sum Up
Chicago offers a diverse array of engaging walking tours that cater to a range of interests. From exploring the city’s rich architectural heritage and culinary scene to delving into its captivating history, these tours provide an immersive and informative experience for visitors. Whether you’re a first-time or seasoned traveler, there’s a walking tour in Chicago to suit your preferences and enhance your exploration of the Windy City.