Top Activities on the Ground in Chicago

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Explore Chicago’s most iconic sites on a 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.

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

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.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your 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 Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

See Chicago your way—and enjoy an active way to explore—with this private, half-day bike rental. Make your own way to the rental facility, choose from a range of bike types (from e-bikes and child bikes to premium road bikes), and set off at your own pace. Accompanied by a map and helmet, you can cycle along the water, explore Millennium Park and the Museum Campus, tour Chicago neighborhoods, and more.

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!"

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.

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.

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.

Experience Chicago like never before—and see more of the sights in less time—on this immersive 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 one-of-a-kind 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.

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. 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. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

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.

An immersive clue-solving adventure around the trendy arts neighborhood Fulton Market. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll never forget! Reschedule anytime with no fees. It's a scavenger hunt, escape room, and urban crawl all-in-one. Follow the storyline around town as you find clues and use them to crack codes. Then enter solutions on the app to find out where to go next. Clues can be anywhere - murals, statues, landmarks, and more! Plan on about two hours of playtime, depending on your experience level and how much time you spend exploring along the way. Difficulty level is adjustable - take as many or as few hints as you’d like! Bookings made a week or more in advance receive their kit in the mail. Bookings made less than a week in advance will pick up their kit at the start point on the day of the adventure - exact pickup location is sent after booking.

Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on our state-of-the-art electric bikes. From iconic landmarks to hidden gems, this unforgettable adventure combines adventure, warmth, and loads of fun. Immerse yourself in the vibrant atmosphere of Milton Olive Park, the wonder of Soldier Field, and capture unforgettable photos at the majestic Buckingham Fountain. With flexible routes and a focus on hidden treasures, our tour offers a truly unique and memorable experience through the heart of Chicago.

The streets of Chicago hold clues to a chilling murder. Can you piece together what happened on this self-guided walking quest? Your smartphone delivers clues, witness statements, and puzzles as you navigate between real-world locations that become your crime scene. Each stop reveals new evidence and suspects. Follow the trail from location to location, piecing together the story while exploring Chicago's streets. The app guides you step by step with an immersive narrative full of twists. This 1–2 hour private detective adventure runs 24/7 — start whenever you want, pause for coffee or photos, and play at your own pace. Available in 5+ languages.

The Best Way to Discover Chicago: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a photo at Maggie Daley Park or a visit to the Shedd Aquarium and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups. The "Complete City" Package - Everything you need in one app: Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way. Audio & Text: Listen to our audio guide or read the history/legends of each site. Insider Tips: Access hand-picked local restaurant and shop recommendations. What you will visit: Navy Pier, Franklin Delano Roosevelt Bridge, Maggie Daley Park, Millennium Park, The Art Institute of Chicago, Clarence F. Buckingham Memorial Fountain, Queen’s Landing, Field Museum, Shedd Aquarium, and Adler Planetarium.

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.

See (and taste) the best of Chicago in just half a day on this bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along the Lakefront Trail, admire views of Millennium Park, and discover the Chicago Riverwalk. As you go, stop to sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, and a tasty dessert for good measure.

Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!