Top Activities on the Ground in Chicago

Pedal past the lakefront neighborhoods of Chicago's North Side on this 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 Chicago light up with a 4-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 daytime or evening views of Millennium Park and the Museum Campus. Sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, and a tasty dessert for good measure. As you pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.

Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.

Discover many of Chicago's best-known landmarks—and explore without breaking a sweat—on this private electric bike tour. Meet your guide right at the Buckingham Fountain, grab your e-bike and helmet, and get ready to explore. You'll view Lakefront landmarks like the Field Museum and Adler Planetarium, will zip right along the waters of Lake Michigan, and will stop to soak up picture-perfect views of the Chicago skyline.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.

Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some 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 vegan, gluten-, and nut-free options are also available.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.

Take in iconic views of the beautiful Chicago skyline and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Explore Chicago at your own pace on an independent bike tour. With your half-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

Zombie Scavengers takes you on an adventure in Chicago to survive the zombie apocalypse! Use our app and some strategy to find a list of items needed to survive, in any order you'd prefer, around the city. Find the survival items to get points and do fun zombie themed challenges for points as well. Contrive a plan to get your survival team the most points in order to survive the apocalypse! Your remote host will follow along virtually and provide support if you need it. Can you survive the apocalypse in Chicago?

This hilarious and fun Outdoor Adventure will navigate you to Chicago's hot spots, highlights and best parts of the city that we know you'll want to visit. You'll discover new places, hidden gems and little nooks that you might want to return to, all while being entertained by the inimitable Inspector Clouseau, as you practice your detective skills and deduce your way to solving the Case of the Missing Diamond.

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before! Use clues and hints within the app to complete the objectives (if you get stuck, you can skip and go back later). Some objectives have prizes so do your best to complete as many objectives correctly. Once complete, you can view the Leaderboard to see how you did against others.

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.

Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.

Bike & Roll Chicago offers a large selection of bicycles. Helmets, locks are included with bicycle rental. We are located at Michigan Ave & Monroe Street across from Millennium Park and one block to the lakefront trail. Drop off at our Navy Pier location is optional.

Chicago was once known as the “Candy Capital of the World,” and chocolate has been a rich, decadent part of the city’s culinary history longer than deep-dish pizza and Italian beef. Milton Hershey even learned how to make chocolate in Chicago at the 1893 World’s Fair and opened up his own company a year later. Also, some of the world’s most beloved chocolate treats, including Tootsie Rolls, Baby Ruth, Butterfinger, Snickers, 3 Musketeers and Milky Way, were invented or are manufactured here. And thanks to the Blommer Chocolate Factory, downtown can even smell like chocolate when the wind is right. There are 8 delicious Loop and River North stops on our scavenger hunt. Simply read the clues and follow the directions to guess the answers to submit. Hints are provided should you need some help. You won’t be required to buy anything, but if you need a quick pick-me-up, what’s better than chocolate? Some locations might be handing out samples, depending on the day. Happy hunting!

Discover Chicago in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure around the Chicago Loop — to the historic buildings, famous streets and plethora of real-life locations around town. Discover both well-known and overlooked sites, solving clues and completing challenges via smartphone while learning the local history of the Windy City. Teams of 2- to 5-people are welcome.

Walk around Chicago while completing the Wacky Walks scavenger hunt. Use an app to find a list of objects around the city and participate in fun challenges for points. Collect points and take a look at your score compared to others around the country! All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Chicago.