Walking tours showcase Chicago’s finest features through expert-led explorations.
The “Chicago in a Day” tour stands out for efficiently combining must-see architecture with essential food stops in just hours.
Architecture buffs will appreciate the Loop Interior tour, which gets you inside stunning lobbies and art deco landmarks normally missed by travelers.
For something different, try the Gangster and Food tour – it mixes authentic Chicago eats with fascinating mob-era stories that shaped the city.
We particularly value tours offering early access to popular sites and those led by certified guides who know their stuff.
The Chicago Architecture Foundation’s offerings consistently deliver high-quality, accurate information.
Let’s explore our favorite Chicago walking tours worth your time and money.
Key Points
The Chicago in a Day: Food, History, and Architecture Walking Tour offers a comprehensive experience, blending culinary delights with cultural insights and architectural appreciation.
The Chicago Walking Food Tour with Secret Food Tours provides a 5-star rated small-group exploration of historic landmarks and eateries, showcasing local specialties.
The Chicago’s Chinatown Food and Walking Tour offers a highly-rated 2-hour experience highlighting iconic eateries, dim sum dumplings, and in-depth cultural insights.
The Chicago Architecture Walking Tour: Dazzling Interiors of the Loop focuses on the hidden interior spaces of Chicago’s architecture, led by experienced local guides.
The Chicago Gangster and Food Walking Tour uniquely blends Prohibition-era stories with culinary experiences, providing a personalized and engaging storytelling experience.
Chicago in a Day: Food, History and Architecture Walking Tour
The Chicago in a Day: Food, History, and Architecture Walking Tour provides visitors with a comprehensive introduction to the city’s rich cultural heritage and culinary delights.
Spanning approximately 5 hours and covering 3-4 miles, this highly-rated tour takes participants on a journey through the heart of Chicago. Along the way, they’ll sample iconic local dishes, including deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs, while also exploring the city’s renowned architecture and historical landmarks.
Led by knowledgeable local guides, the tour offers an engaging and informative experience, with numerous positive reviews praising the guides’ expertise and the tour’s ability to blend food and cultural insights.
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
A unique perspective on Chicago’s architectural marvels awaits visitors who embark on the Chicago Architecture Walking Tour: Dazzling Interiors of the Loop.
With 974 glowing reviews and a 99% traveler recommendation, this tour offers an immersive exploration of the city’s hidden interior spaces.
Led by experienced local guides, participants learn about the history, art, and design that define Chicago’s renowned architecture.
Customized itineraries cater to individual interests, while the small group size of 20 or fewer ensures personalized attention.
Whether a first-time visitor or a Chicago local, this tour promises a fun and educational experience that highlights the city’s unique heritage and architectural gems.
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Chicago Walking Food Tour With Secret Food Tours
For those seeking to savor the diverse culinary delights and architectural marvels of Chicago, the Chicago Walking Food Tour with Secret Food Tours offers an unparalleled experience.
Priced from $89, this highly-rated 5-star tour takes small groups of up to 12 travelers on a journey through the city’s historic landmarks and famous eateries.
Guests indulge in a mouthwatering lineup of local specialties, including deep-dish pizza, Chicago-style hot dogs, and a secret dish revealed on the day.
Complemented by insights from knowledgeable local guides, the tour provides a well-rounded exploration of Chicago’s iconic food scene and architectural wonders.
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Chicago Walking Tour: Art Deco Skyscrapers Loop
Offering a captivating exploration of Chicago’s iconic art deco architecture, the Chicago Walking Tour: Art Deco Skyscrapers Loop immerses visitors in the city’s rich architectural heritage.
Led by Chicago Architecture Center-certified guides, this small-group tour focuses on the art deco masterpieces of the Loop, often overlooked by other tours.
Participants can expect to admire highlights such as the Rookery Building, 135 South LaSalle Street, and the Chicago Board of Trade Building, while also gaining access to the Galleries of the Chicago Architecture Center.
With rave reviews, this tour is a must for architecture enthusiasts and history buffs seeking an immersive experience in the heart of downtown Chicago.
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Chicago Gangster and Food Walking Tour
Immersing visitors in the captivating history of Chicago’s underworld, the Chicago Gangster and Food Walking Tour blends Prohibition-era stories with the city’s renowned culinary delights.
With over 450 reviews and a 95% recommendation rate, this unique experience has earned a Badge of Excellence from Chicago Tours.
Highlighting the connection between gangster hideouts and famous food destinations, the small-group tour offers personalized attention to its guests.
While reviews express mixed opinions on the food quality, the knowledgeable and engaging guides consistently receive praise for their ability to bring the city’s past to life.
The tour concludes near the Magnificent Mile, offering easy access to further exploration of Chicago.
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Chicago Walking Tour: Historic Treasures of Chicago
The Chicago Walking Tour: Historic Treasures of Chicago invites visitors on a captivating exploration of the city’s architectural wonders.
Led by professional and certified guides, this walking tour showcases the city’s iconic buildings and their rich histories. With a maximum group size of 15, the tour provides an intimate and engaging experience, complete with access to the Chicago Architecture Center’s galleries.
Praised for its knowledgeable and enthusiastic guides, the tour is a fantastic way to learn about Chicago’s architectural heritage.
The tour’s flexibility, with wheelchair and stroller accessibility, ensures a comfortable and inclusive experience for all.
Whether you’re a history buff or an architecture enthusiast, this walking tour promises an unforgettable journey through Chicago’s historic treasures.
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Chicago Architecture Walking Tour: The Underground Pedway & Secrets of the Loop
Travelers embark on a captivating exploration of Chicago’s underground Pedway system and the hidden gems of the Loop during the Chicago Architecture Walking Tour.
Featuring 207 reviews with a 97% traveler recommendation, this small-group tour showcases the city’s renowned architecture, including the iconic Picasso Statue and Millennium Park.
Knowledgeable and engaging guides, such as Colleen, Adam, Heath, and Kaylee, lead participants through the Windy City’s underground network and reveal secrets often missed by locals.
Visitors appreciate the unique perspective, especially during adverse weather conditions, and the opportunity to discover aspects of Chicago they’ve never seen before.
While some guests desire more emphasis on architectural styling, the tour provides an educational and enjoyable experience for architecture enthusiasts and first-time visitors alike.
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Chicago Walking Tour: A Walk Through Time
Offering a captivating journey through Chicago’s architectural heritage, the Chicago Walking Tour: A Walk Through Time takes visitors on an enlightening exploration of the city’s renowned buildings.
Highly recommended by travelers, the 161 five-star reviews and a Badge of Excellence from the Chicago Architecture Center speak to the tour’s exceptional quality.
Led by knowledgeable guides, the small-group experience provides in-depth commentary on the city’s architectural history while offering access to exclusive locations like the Automobile Association building foyer.
With a starting price of $30 and free cancellation up to 24 hours in advance, this tour is an excellent choice for first-time or time-pressed visitors seeking an immersive and engaging introduction to Chicago’s rich architectural legacy.
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Chicagos Chinatown Food and Walking Tour
Immersing visitors in the vibrant flavors and rich cultural heritage of Chicago’s Chinatown, the Chinatown Food and Walking Tour offers an unparalleled culinary and sightseeing experience.
With a 5.0 rating and 98% traveler recommendation, this 2-hour tour guides a maximum of 15 guests through the neighborhood, stopping at iconic eateries like Phoenix Restaurant and Chiu Quon Bakery.
Highlights include dim sum dumplings, Xian-style noodles, Szechuan hot pot, and a traditional Chinese tea service.
Knowledgeable guides share insights into the area’s history and culture, while guests savor generous portions of diverse cuisines.
Priced at $79.99, the tour offers vegetarian options and a VIP upgrade for alcoholic beverages.
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Downtown Chicago Walking Pizza Tour
The Downtown Chicago Walking Pizza Tour takes participants on a delectable journey through the city’s celebrated pizza culture.
Over 3.5 hours, small groups of up to 16 travelers sample a variety of pizza styles, from deep-dish to artisanal. Knowledgeable guides lead the way, sharing insights into Chicago’s culinary history and showcasing key landmarks.
The tour covers iconic neighborhoods like the Loop and River North, with enough pizza samples to make a full meal.
Travelers consistently praise the tour’s delicious food, engaging commentary, and personalized service, with specific guides like James and John earning rave reviews.
For a filling and informative exploration of Chicago’s pizza scene, this walking tour is a must-try.
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Chicago City Walking Tour
Explore the heart of Chicago on a comprehensive walking tour that showcases the city’s renowned architecture, iconic landmarks, and captivating history.
The “Best of Chicago: Architecture & Highlights City Private Tour” offers a 3-hour guided experience, covering top attractions like the Willis Tower, Millennium Park, and the Magnificent Mile.
With a flexible itinerary, knowledgeable local guides, and included transportation passes, this tour provides an immersive and customizable way to discover the city.
Priced at $320 for up to 12 participants, the tour features free cancellation and a pay-later option, ensuring a hassle-free booking process.
Rated 5/5 by previous travelers, this walking tour promises an unforgettable exploration of Chicago’s rich culture and stunning cityscapes.
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Chicago TV & Movie Locations Walking Tour
This 3-hour Chicago TV & Movie Locations Walking Tour takes participants on an immersive journey through the city’s iconic film and television backdrops.
Starting from Chicago City Hall, the tour explores the Chicago Loop, the Riverwalk, Union Station, and Millennium Park, where numerous blockbusters were filmed.
Along the way, the local guide shares insider stories and provides food and drink recommendations.
Highlights include witnessing the Marina Towers featured in The Hunter and visiting filming locations for movies like The Dark Knight and Ferris Bueller’s Day Off.
With a flexible cancellation policy and the option to ride the ‘L’ train, this tour offers a unique and engaging way to experience Chicago through the lens of Hollywood.
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Chicago Lincoln Park Ghost Stories Small-Group Walking Tour
Participants on the Windy City Ghosts: Hauntings of Chicago Walking Tour embark on a captivating exploration of Lincoln Park’s spooky lore.
Led by knowledgeable and engaging guides, the tour delves into true stories of haunted history, with documented accounts of paranormal activity. Guests appreciate the blend of local history and spine-tingling storytelling, although some desire more in-depth ghost tales.
The tour’s accessibility, with wheelchair-friendly routes and transportation options, makes it inclusive for all. While a moderate fitness level is recommended, the approximately one-hour duration provides an immersive experience for adventurous travelers seeking a glimpse into Chicago’s ghostly past.
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Holiday Hike Chicago-Style: Festive Food & Walking Tour
Embarking on a delightful exploration of Chicago’s festive highlights, the Holiday Hike Chicago-Style: Festive Food and Walking Tour invites visitors to enjoy the city’s vibrant holiday atmosphere.
Led by friendly local guides, the 3-hour tour takes participants on a journey through iconic landmarks like Millennium Park and the Palmer House Hilton. Along the way, guests savor local specialties, including deep-dish pizza and Chicago-style hot dogs.
The tour also includes visits to the Christkindlmarket and State Street’s dazzling holiday displays. With a maximum group size of 15, this wheelchair-accessible tour offers a personalized experience for first-time and returning visitors alike.
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Chicago Walking Tour: Tiffany Treasures
The Chicago Walking Tour: Tiffany Treasures immerses participants in the dazzling world of late-19th-century stained glass masterpieces.
This small-group tour, capped at 10 people, explores four architectural landmarks, focusing on the stunning Tiffany works. Guests will marvel at mosaics, vaults, and light fixtures as they learn about the history and restoration efforts of these breathtaking pieces.
The tour concludes at the Marquette Building, where admission to the Chicago Architecture Center galleries is included.
With a knowledgeable guide, wheelchair accessibility, and convenient public transportation, this 2-hour experience is perfect for architecture and history enthusiasts seeking a personal, in-depth exploration of Chicago’s Tiffany treasures.
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Chicago Architecture Walking Tour: Whats New
This immersive virtual tour from the Chicago Architecture Center showcases the city’s architectural evolution, guiding participants through the diverse styles shaping its modern skyline.
Led by a professional and certified guide, the experience delves into architectural movements like brutalism and modernism, highlighting significant structures from the early 20th century to the present day.
Admission to the center’s galleries is included, and the small group size of 15 travelers ensures an intimate, interactive experience.
With wheelchair accessibility and proximity to public transportation, this virtual tour offers an engaging and accessible way to explore Chicago’s renowned architecture without leaving home.
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Workers Cottages of Oldtown Triangle Walking Tour
Venturing beyond Chicago’s iconic skyscrapers, the Workers Cottages of Oldtown Triangle Walking Tour invites participants to step back in time and explore the charming residential enclaves that have defined the city’s architectural landscape.
Offering a unique perspective on Chicago’s history, the 45-minute stroll highlights the well-preserved worker’s cottages that thrived in the Oldtown Triangle neighborhood.
Travelers can expect to learn about the area’s evolution, guided by the tour’s passionate leader, Ronnie.
With a maximum group size of 8 and a moderate fitness level required, this highly recommended tour provides an immersive experience for those interested in local history and architecture, complete with historical photos accessible through a free app.
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Chicago Walking Tour: Art Deco Skyscrapers Riverfront
One of Chicago’s must-do walking tours, the Chicago Walking Tour: Art Deco Skyscrapers Riverfront, transports participants on a captivating journey through the city’s iconic architectural landscape.
With a 5.0 rating and 100% traveler recommendation, this 2.5-hour excursion offers an up-close look at the city’s celebrated art deco skyscrapers along the riverfront.
Led by a certified guide, the tour includes admission to the Galleries of the Chicago Architecture Center and convenient amenities like coat check and luggage storage.
Whether you’re a first-time visitor or a Chicago enthusiast, this immersive experience promises to showcase the city’s architectural gems in a new light.
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Chicago Walking Tour: Modern Architecture
Enjoy Chicago’s captivating modern and postmodern architectural landscape on the Chicago Walking Tour: Modern Architecture.
Explore iconic works by renowned architects like Mies van der Rohe and Bertrand Goldberg, and explore the insider stories and historical context provided by the knowledgeable guides.
With a maximum group size of 15, this tour offers a personal experience perfect for architecture enthusiasts and history buffs.
Admission to the Galleries of the Chicago Architecture Center is included, allowing you to further learn about the city’s architectural wonders.
While the tour mightn’t appeal to everyone, the overwhelming positive reviews and the Badge of Excellence suggest an engaging and informative experience.
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Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
Travelers seeking a personalized exploration of Chicago can embark on the “Your Way or the Highway” private walking tour.
This 2-hour experience offers a customized itinerary, led by a CTPA licensed guide. Priced at $220 for up to 6 people, the tour showcases the city’s highlights, hidden gems, and architectural wonders.
Highly rated for its knowledgeable and friendly guides, the tour can be tailored to individual interests. Participants can expect a wheelchair-accessible experience near public transportation, with the option to include alcoholic beverages, lunch, and snacks.
With a perfect 5.0 rating and free cancellation up to 24 hours in advance, this tour provides a unique and memorable way to discover Chicago.
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Break Down
Chicago offers a diverse range of walking tours that cater to various interests. From food and history to architecture and modern design, visitors can explore the city’s rich cultural heritage and iconic landmarks. Whether you prefer a guided group tour or a customized private experience, there’s a walking tour in Chicago to suit every traveler’s preferences and needs.