Top Chicago Walking & Biking Tours

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Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs

• 52 Reviews
• Stroll through downtown Chicago on this 2.5-hour food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, brownies, and local beer. All tastings and beverages are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
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Historic Chicago Walking Bar Tour

• 27 Reviews
• Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social clubs, and the Prohibition era in the Windy City as you take in historic buildings and architecture. Use iPads to view historic photos and videos that accompany your guide’s stories as you stop in both famous and hidden bars for drinks and appetizers. A short walk allows plenty of time to see Chicago’s famous architecture and pubs on this tour – great for visitors and locals alike!
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Underground Donut Tour - Chicago's First Donut Tour

• 5 Reviews
• Sample some of the Windy City’s tastiest donuts on this 2-hour Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit four of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and gluten- and nut-free options are also available.
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Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

• 95 Reviews
• Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this 2-hour walking tour. Your expert guide will share insights about interior architectural features of this design-rich city — from mosaic domes to the sprawling Chicago Pedway System — bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes, and Hot Dogs

• 55 Reviews
• Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this 4-hour bike tour through the windy city. You’ll cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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Chicago Lakefront Neighborhoods Bicycle Tour

• 42 Reviews
• Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
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Chicago Pedway Walking Tour

• 77 Reviews
• Discover a lesser-known side of the Windy City on this Chicago Pedway tour, a 1.5-hour walking excursion through the many heated passageways, tunnels, and corridors that link some of the town's most iconic buildings. Follow your humorous guide on an insider's exploration of these relatively unknown walkways, learning about the area's architecture and history as you go. It's a great way to explore a different side of Chicago unknown to most visitors.
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3-Hour Walking Tour: Chicago World's Fair of 1893

• 1 Review
• Discover the lasting influence of the 1893 World’s Fair in Chicago on a 3-hour walking and food tour of downtown. See the historic Auditorium Building, the Chicago Athletic Association Hotel and other examples of Chicago’s fine architecture. You’ll also sample fresh–brewed beers and some tasty German fare among other refreshments, with enough food for a light meal. Your guide provides informative commentary and entertaining games during your Chicago walking tour, which mostly takes place indoors, making it ideal for all seasons.
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Urban Sketching Downtown Chicago with a Watercolor Artist

• We will be sketching the urban landscape of downtown Chicago using pencil, pen, and watercolors. During this two and a half hour experience you will learn the basics of Urban Sketching and complete at least one piece of art work. I'll show you how to let your guard down and your inner artist out. During the cooler days, if it's raining, or snowing we'll sketch inside at one of the many Chicago architectural gems.
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

• 7 Reviews
• See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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Chicago Architecture Walking Tour: High-Up and Low-Down Views of the City

• Get great views of Chicago on a walking tour that has special access to buildings not open to the general public. Your guide leads you to places with fantastic perspectives of the Windy City, and gives you time for photo ops throughout the 2-hour tour. Hear insightful commentary about the city as you cover about 1.5 miles on foot, walking at a leisurely pace with frequent stops.
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Old Polonia and Wicker Park History and Food Tour

• 1 Review
• Explore the past and present of two Chicago neighborhoods on this guided, 2.5-hour walking tour. Visit Wicker Park, once infamous as a home for gang bangers, drug addicts and prostitutes, it’s now widely considered one of the trendiest neighborhoods in America. Then walk through the West Town district of Noble Square, formerly known as ‘Old Polonia.’ Along the way, see many popular points of interest and enjoy food tastings at some of the area’s best eateries.
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Chicago Bike Tour

• Experience the top sights of the Windy City on a 3.5-hour guided bike tour. Traveling on two wheels allows you to skip the sluggish pace of city traffic and avoid the limitations of walking. Let your guide take care of narration and navigation as you ride through eight neighborhoods, including Lincoln Park and Old Town. Stop for photos as you pedal onwards to the city’s lakefront and beyond.
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Chicago Holiday Stroll and Food Tour

• 3 Reviews
• Stroll through Chicago's winter streets, lit up for the holidays, on this 3-hour walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows at Macy's, and ice skating at Millennium Park. Follow your local guide on a walk down festively decorated State Street and sample generous tastes of classic Chicago foods and holiday treats. Seasonal craft beer tastings will help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
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Chicago Lincoln Park Bike Adventure

• 3 Reviews
• Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.
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Chicago Architecture Walking Tour for Design Lovers

• See Chicago from a new perspective with this art- and pop culture-themed architectural walking tour. Follow an informative guide through the city’s streets, from the Michigan Avenue Bridge to the new Maggie Daley Park, while learning about the city’s history, architecture, and the fascinating connections between art history and Chicago architectural styles. Enrich your understanding of this beautiful American city with this fun and affordable outing.
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Chicago Loop Walking Tour

• 3 Reviews
• Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.
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Chicago Tastes of Chinatown Walking Food Tour

• 3 Reviews
• Explore Chicago's Chinese food scene on this 3-hour walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. You'll enjoy included tastings from restaurants and other food venues in Chinatown — a great way to start a night out in the city.
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Bites and Brews Bicycle Tour in Chicago

• Taste food from around the world on this 4-hour cycling tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Mexican tortas, French sweets, and Polish pierogis.
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Chicago Crime and Pizza Walk

• Explore the River North and Gold Coast neighborhoods in Chicago during a 2-hour walking that focuses on the city's famous deep-dish pizza and most notorious criminals.
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Walking Tour of Lincoln Park in Chicago

• 1 Review
• Step off the tourists’ path to visit Lincoln Park, a neighborhood beloved by Chicagoans for its stately homes, historic zoo, and stunning green areas. Your tour begins at the charming Children’s Fountain and continues to unexpected sites like the shrine of the first American saint. As your local guide leads you through the city’s largest park, you’ll marvel at the wild feel of this neighborhood just north of downtown Chicago.
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Chicago River Walking Tour

• 1 Review
• A river runs through it: the Chicago River passes right through the heart of downtown and is a major part of city identity. You’ll begin this walking tour at Navy Pier and follow your local guide along the scenic river walk. You’ll learn the role of the river in Chicago’s history, and stop to admire iconic architecture and bridges celebrated as feats of engineering.
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Chicago's Greatest Hits Bicycle Tour

• Explore Chicago’s most iconic sites with a 2.5-hour bike tour that explores Museum Campus, parks and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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Fright Hike: Halloween Edition Chicago Bike Tour

• Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.
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