Walking & Biking Tours in Chicago

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.

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.

Enjoy two Chicago experiences at one price with this combo bike tour and admission to the Skydeck Chicago at Willis Tower. With a guide, you'll ride through eight neighborhoods and along the Lake Michigan waterfront to take in the city's attractions and scenery, listening to stories and history about Chicago as you go. Then visit the Skydeck for a 360-degree view from 1,353 feet (412 meters) in the air.

Discover the sights and sounds of Chicago's various cultural scenes on a 2-hour walking tour. The 1.5-mile route covers music, literature, art, and architecture within the Windy City. Hear insider stories about Chicago's cultural movements and visit little-known locations linked to iconic artists.  Be sure to have your camera ready for the pièce de r esistance, the Tiffany stained glass dome at the Chicago Cultural Center.

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.

Ride a bicycle through Chicago's Museum Campus and take in the city sights during a 2.5-hour nighttime ride. View illuminated attractions and pedal along pathways to Buckingham Fountain to see its feast of lights. Finish your guided bike tour at Navy Pier and watch its legendary fireworks display reflected on Lake Michigan and the city skyline. Number of participants is limited to ensure a small-group experience.

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.

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.

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.

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.

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.

See Chicago light up at night with a 3-hour bicycle tour of the Windy City's most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in evening views of Millennium Park and the Museum Campus. Pedal through downtown streets, capture unforgettable images of Chicago's magnificent skyline then finish your tour in the heart of the city.

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.

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!

Learn the stories behind the skyscrapers on a 2-hour walking tour of Chicago's architectural history and highlights. Follow your knowledgeable guide through the Loop district,  take in the city's most important buildings and get a new perspective on the Second City skyline. Enjoy the bustling streets of this diverse, vibrant neighborhood as you compare buildings across time and contrast works by the same architect. You'll never look at Chicago's iconic building the same way again.

Cruise through Chicago on this family-friendly bicycle tour catered to kids. Perfect for kids age 10 and under, this tour mixes fun games and contests in with educational stops at some of Chicago's iconic sights. Parents can ride along with their children on cruiser-style bikes during this safe, enjoyable 2-hour tour that covers an easy 4.5 miles (7 km).

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.

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.

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.