Chicago’s walking tours efficiently connect visitors with the city’s essential sights and stories. The best guided walks focus on three main themes: architecture, food, and history.
The Loop architecture tours stand out for their expert commentary on world-famous buildings and access to stunning interior lobbies. Along the river, guides explain the evolution of Chicago’s skyline while pointing out art deco masterpieces.
Food tours through Chinatown and downtown deliver authentic tastes at family-run spots that locals love. We especially like the neighborhood food walks that combine sampling with cultural insights.
History-focused tours balance Chicago’s fascinating gangster stories with broader cultural context, making complex history easy to understand. The vintage crime tours are particularly well-researched and entertaining.
Check out our top-rated walking tours below to find your perfect Chicago adventure.
Good To Know
- Chicago offers a diverse range of walking tours, including architecture, food, history, and comprehensive tours that showcase the city’s top landmarks and attractions.
- Many of the walking tours in Chicago are highly rated and recommended by over 95% of travelers, ensuring a quality experience.
- The Chicago in a Day: Food, History and Architecture Walking Tour is a popular option that combines the city’s culinary, historical, and architectural highlights in a single tour.
- Customized private walking tours in Chicago allow for a personalized exploration of the city, catering to specific interests and preferences.
- These walking tours are led by knowledgeable and experienced guides, providing valuable insights and unique perspectives on Chicago’s rich history and vibrant culture.
Chicago in a Day: Food, History and Architecture Walking Tour
Exploring the city’s vibrant food scene, iconic architecture, and captivating history, the Chicago in a Day: Food, History and Architecture Walking Tour offers a comprehensive introduction to the Windy City. Recommended by 98% of travelers, this small-group tour takes you on a 4-in-1 adventure, covering the city’s top landmarks, culinary highlights, and Prohibition Era legacy.
You’ll savor four local food specialties, from deep-dish pizza to Chicago-style hot dogs, while discovering the city’s incredible architecture and gaining insider tips on what else to see, do, and eat during your stay. Suitable for all ages and fitness levels, this tour is an excellent choice for first-time visitors seeking a well-rounded exploration of Chicago.
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
Venture beyond the bustling streets of Chicago’s Loop and uncover the dazzling interiors that define the city’s architectural legacy. This two-hour walking tour offers a unique local perspective, guiding you through the hidden gems of the Loop district.
Explore the stunning interiors of Chicago’s most iconic buildings, where art and history collide. With a maximum group size of 20, you’ll enjoy a personalized experience led by a knowledgeable local guide. Dress appropriately, as the tour operates in all weather conditions.
Discover the city’s architectural wonders, from the Chicago Cultural Center to the Financial District, on this highly-rated, 5.0-star tour that’s perfect for both locals and visitors.
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Chicago Walking Food Tour With Secret Food Tours
Enjoy Chicago’s vibrant food scene and architectural wonders on this highly-rated walking tour. With a 4.9 rating from 630 reviews and a 98% recommendation rate, this small group or private tour is a must for any foodie or architecture enthusiast.
You’ll taste classic Chicago dishes like deep-dish pizza, Italian beef sandwiches, and more, while exploring the Loop’s iconic landmarks, including the Willis Tower and Rookery Building. The tour also includes a surprise secret dish, adding an element of excitement.
With a local guide leading the way, you’ll dive deep into the city’s culinary and architectural heritage. Don’t miss this chance to experience the best of Chicago on foot.
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Chicago Walking Tour: Art Deco Skyscrapers Loop
If you’re captivated by Chicago’s architectural marvels, the Chicago Walking Tour: Art Deco Skyscrapers Loop offers a unique opportunity to explore the city’s stunning Art Deco skyscrapers. Led by a Chicago Architecture Center-certified guide, this small-group tour takes you on a journey through the Loop, unveiling the ornamental facades and interiors of these iconic buildings.
You’ll learn about the Art Deco architectural movement and its influence on Chicago’s history. Included in the tour is admission to the Galleries of the Chicago Architecture Center, providing an in-depth look at the city’s architectural heritage. With a maximum of 10 travelers, this tour ensures an intimate and personalized experience, making it a must-do for architecture enthusiasts visiting Chicago.
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Chicago Gangster and Food Walking Tour
Set out on a captivating journey through Chicago’s storied past with the Chicago Gangster and Food Walking Tour. Enjoy the city’s Prohibition-era history as you visit iconic sites like a legendary steakhouse and a renowned deep-dish pizza spot.
Indulge in three delectable food tastings, including Chicago’s signature steak and hot dog. Sip on alcoholic beverages as your knowledgeable guide unveils the city’s gangster secrets. This small-group tour offers an engaging and flavorful experience, with a meeting point conveniently located near public transportation.
While not wheelchair accessible, it welcomes service animals and infants. With a remarkable 4.8 rating and 95% recommendation, this tour promises an unforgettable exploration of Chicago’s rich history and iconic cuisine.
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Chicago Walking Tour: Historic Treasures of Chicago
On this Chicago Walking Tour: Historic Treasures of Chicago, you’ll explore the city’s stunning architecture and uncover its rich history. Led by a professional and certified guide, you’ll embark on a walking tour that showcases the best of Chicago’s historic landmarks.
With a 4.9-star rating and recommended by 99% of travelers, this small-group tour offers a personal way to see the city. You’ll gain exclusive access to the Galleries of the Chicago Architecture Center and discover hidden gems that many visitors miss.
Plus, you’ll end your tour at the iconic Chicago Cultural Center, leaving you well-versed in the city’s architectural and cultural heritage.
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Chicago Architecture Walking Tour: The Underground Pedway & Secrets of the Loop
Explore the hidden world beneath Chicago’s bustling streets on this captivating Chicago Architecture Walking Tour. You’ll discover the underground network of the Pedway, where you’ll see Chicago gems often overlooked by locals and travelers.
Led by a knowledgeable local guide, you’ll visit the iconic Picasso Statue and marvel at the architectural wonders of Millennium Park. This tour is ideal for architecture enthusiasts, offering a unique perspective on the city’s hidden gems.
With moderate physical fitness required, you’ll navigate the Pedway and the Loop, learning about the city’s history and design. Don’t miss this chance to uncover the secrets of Chicago’s underground world.
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Chicago Walking Tour: A Walk Through Time
For those short on time but eager to soak up Chicago’s rich architectural history, the Chicago Walking Tour: A Walk Through Time is an ideal option. This express, small-group walking tour covers the city’s most famous buildings in chronological order, led by a professional and certified guide.
You’ll gain admission to the Galleries of the Chicago Architecture Center, and the tour’s 98% traveler recommendation speaks to its quality. Spanning just over an hour, this walking tour provides an efficient and informative introduction to Chicago’s architectural highlights, perfect for first-time or time-pressed visitors. With a maximum of 15 travelers per group, you’ll enjoy a personalized experience in a compact timeframe.
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Chicagos Chinatown Food and Walking Tour
Enjoy the vibrant flavors and rich culture of Chicago’s Chinatown on this engaging food and walking tour. With a 4.9 rating from 353 reviews and a 98% recommendation, you’ll enjoy a 2-hour adventure led by a local guide.
Savor dim sum dumplings, regional dishes like spicy meat sandwiches and Szechuan hot pot, and end at a historic bakery for a custard tart. The tour operates in all weather conditions and accommodates up to 15 travelers.
Enjoy alcoholic beverages with a VIP upgrade, and don’t forget to tip your guide. This wheelchair-accessible tour is conveniently located near public transportation, though minimum numbers are required for it to run.
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Downtown Chicago Walking Pizza Tour
Embark on an appetizing adventure through downtown Chicago’s diverse pizza landscape on this walking tour. You’ll explore an array of pizza styles, from deep-dish to Neapolitan and beyond, while learning about the city’s culinary heritage. Enjoy a personalized experience with a small group and a professional guide, who’ll lead you to key landmarks.
With enough samples to satisfy your hunger, the tour includes a generous lunch. Though gratuities and drinks aren’t covered, the tour’s affordable price and high ratings make it a must-try for any pizza enthusiast visiting Chicago. Cap off your day by spotting the city’s iconic sights as you savor your final slice.
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Chicago City Walking Tour
Discover the vibrant heart of Chicago on this comprehensive city walking tour. You’ll explore the Windy City’s iconic landmarks, from the stunning architecture of the Loop to the lively Magnificent Mile. With an expert local guide, you’ll dive into Chicago’s rich history and culture, riding the ‘L’ train and enjoying a tasty local snack along the way.
Don’t miss the chance to ascend the Willis Tower or visit the Museum of Contemporary Art for an additional fee. This private tour is wheelchair accessible and provides a $5 public transportation pass, ensuring a seamless and enjoyable experience. Enjoy the best of Chicago during this 3-hour walking adventure.
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Chicago TV & Movie Locations Walking Tour
On this Chicago TV & Movie Locations Walking Tour, you’ll uncover the city’s cinematic side. Over 3 hours, a local guide will lead you through iconic spots featured in blockbuster films and TV shows.
Stroll the Chicago Riverwalk, snap photos at Millennium Park’s “The Bean,” and ride the ‘L’ train. Discover filming locations for The Dark Knight and Ferris Bueller’s Day Off. Explore the grand Chicago Union Station and the Chicago Loop’s historic skyscrapers.
This private, wheelchair-accessible tour costs $320 for up to 12 participants, including a $5 ‘L’ train pass. With free cancellation up to 24 hours in advance, it’s a flexible way to see Chicago’s silver screen highlights.
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Chicago Lincoln Park Ghost Stories Small-Group Walking Tour
Venture into the shadowy realms of Lincoln Park as you uncover the capital city’s eerie ghost stories on this captivating small-group walking tour. Explore supposedly haunted locations like burial grounds, pubs, and theaters, and listen to intensely researched true stories and documented accounts of hauntings.
With a professional and courteous guide, you’ll embark on an approximately 1-hour journey through Chicago’s spookiest sites. Upgrade your experience for an extended tour with even more chilling tales.
With a maximum of 15 travelers, this small-group tour offers a personalized and immersive ghost hunt. Confirmed within 48 hours, this wheelchair and stroller-accessible tour allows free cancellation up to 24 hours before.
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Holiday Hike Chicago-Style: Festive Food & Walking Tour
Step into the heart of Chicago’s winter wonderland on this captivating Holiday Hike that blends festive flavors, local traditions, and architectural marvels. Over 3 hours, you’ll stroll through the city, sampling classic Chicago treats, tasting seasonal brews, and exploring iconic holiday attractions.
Savor deep-dish pizza, the famous Chicago-style hot dog, and more, all while learning about the city’s festive customs. Admire the Millennium Park ice rink, marvel at the official Christmas tree, and learn about the German-inspired Christkindlmarket. Led by a knowledgeable local guide, this tour offers a delightful taste of Chicago’s winter magic. Dress warmly and prepare for an unforgettable holiday adventure.
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Chicago Walking Tour: Tiffany Treasures
Discover the hidden architectural gems of Chicago on this captivating Tiffany-focused walking tour. You’ll explore iconic late-19th-century landmarks and marvel at the stunning stained glass works crafted by the renowned Tiffany Glass and Decorating Company.
Led by a certified Chicago Architecture Center guide, this small-group tour offers a personal experience as you explore the history and restoration efforts behind these artistic treasures. From mosaics and vaults to domes and light fixtures, you’ll uncover architectural details that often go unnoticed.
The tour culminates at the Chicago Architecture Center, where you can continue your exploration of the city’s rich design heritage.
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Chicago Architecture Walking Tour: Whats New
Explore Chicago’s vibrant architectural landscape through this captivating walking tour that showcases the city’s latest design wonders. Led by a professional and certified guide from the Chicago Architecture Center, the tour delves into diverse styles, from early 20th-century opulence to cutting-edge modern structures.
You’ll have access to the center’s galleries, and the tour is wheelchair and stroller accessible. The meeting point is the center itself, with the tour ending at the same location.
Keep in mind that access to building interiors is subject to change, and pets aren’t allowed. With a maximum of 15 travelers, this virtual Zoom experience is a must for architecture enthusiasts.
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Workers Cottages of Oldtown Triangle Walking Tour
The Workers Cottages of Oldtown Triangle Walking Tour takes you on a captivating journey through the historic charms of Chicago’s past. You’ll leave behind the modern buzz of the Windy City and witness fantastic architecture, national landmarks, and hear stories of the city’s often wild history.
The 1-hour tour is limited to just 8 travelers for a personalized experience. You’ll see dozens of classic workers cottages from the mid-1800s and learn about the Oldtown Triangle neighborhood, its notable celebrities, and landmarks. The tour includes historical photos in a free app, and while it’s not wheelchair accessible, it’s stroller-friendly and near public transportation. Travelers should have a moderate fitness level.
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Chicago Walking Tour: Art Deco Skyscrapers Riverfront
Chicago’s stunning art deco skyscrapers along the riverfront offer a captivating glimpse into the city’s architectural past. This small-group tour takes you inside five notable art deco towers, revealing details often overlooked by visitors.
Led by a professional and certified guide, you’ll explore the buildings’ grand interiors and learn about their fascinating histories. The tour is perfect for architecture enthusiasts and history buffs alike, allowing you to soak up the city’s ambiance on foot.
With admission to the Galleries of the Chicago Architecture Center and a coat check included, you’re guaranteed an immersive and memorable experience. Don’t miss this opportunity to discover Chicago’s art deco gems.
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Chicago Walking Tour: Modern Architecture
This walking tour offers a captivating exploration of Chicago’s modern and postmodern architectural marvels. Led by a professional and certified guide, you’ll be immersed in the city’s stunning landscape of sleek, cutting-edge buildings.
With a small group of no more than 15 travelers, you’ll enjoy a personal and intimate experience, exploring the Galleries of the Chicago Architecture Center. The tour is highly recommended, with a 4.9 rating from 43 reviews and a 96% recommendation rate.
While the tour is subject to change, you can expect to be dazzled by the city’s modern architectural gems, all while learning about their history and design. This tour is perfect for architecture enthusiasts and history lovers alike.
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Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
If you’re looking for a personalized way to explore Chicago, the “Your Way or the Highway: 2-hour Customized Private Walking Tour” offers a unique opportunity to discover the city on your own terms. The tour is led by a CTPA licensed guide who’ll focus on your specific interests, whether it’s history, architecture, street art, or food.
You can choose the language, with tours available in English, French, and Dutch. The tour accommodates up to 6 people and ends at a different location than the meeting point, providing personalized recommendations for post-tour activities. With a flexible schedule and 100% traveler recommendation, this customized tour is the perfect way to explore Chicago your way.
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Frequently Asked Questions
What Is the Best Time of Year to Visit Chicago?
The best time to visit Chicago is during the spring or fall when you’ll enjoy mild temperatures, fewer crowds, and a lively cultural scene without the extreme heat or cold of summer and winter.
How Much Walking Is Involved in These Tours?
The amount of walking varies across tours, but you can expect to cover several miles during the average Chicago walking tour. Be prepared with comfortable shoes and be ready to learn about the city’s sights and sounds.
Are the Tours Wheelchair/Stroller Accessible?
The tours are generally wheelchair and stroller accessible, with most routes designed to accommodate mobility needs. Be sure to check with the tour operator ahead of time to confirm accessibility details for your specific tour.
Can I Customize the Tour to My Interests?
Yes, you can usually customize walking tours to match your interests. Many tour operators allow you to tailor the route, pace, and focus to suit your preferences, so you can get the most out of your experience.
What Should I Bring on the Walking Tours?
What to bring on walking tours? Pack light – wear comfortable shoes, bring water, and carry a small backpack or bag for any purchases. Don’t forget your camera to capture the sights along the way!
The Sum Up
No matter your interests, you’ll find a walking tour in Chicago that’s perfect for you. Whether you want to discover the city’s architectural wonders, indulge in its delicious cuisine, or learn about its fascinating history, there’s a walking tour to suit your needs. So get out there and explore the Windy City on foot – you won’t be disappointed.