Things to Do in Chicago

Get ready for an unforgettable experience at the 360 Chicago Observation Deck, located on the 94th floor of 875 North Michigan Avenue (John Hancock Center)! With 360 Chicago tickets, soak in breathtaking panoramic views of the Windy City and Lake Michigan from 1,000 feet above the Magnificent Mile. Elevate your Chicago trip with this must-see attraction! Details

One of the country’s longest-running dinner attractions, Medieval Times Dinner and Tournament Illinois, offers a fun and exciting way to enjoy a feast with family or friends. Guests can enjoy a banquet-style four-course feast (without silverware) while watching six brave knights compete in skill games atop their beautiful Andalusian stallions. Details

This Chicago architecture boat tour by Wendella showcases over 50 architectural landmarks like Marina City and Willis Tower in 45- or 90-minute options. Enjoy narrated skyline views from open-air decks or climate-controlled interiors. Each cruise blends history, design, and unforgettable riverfront perspectives. Details

Flyover Chicago tickets give you access to an immersive flight experience at Navy Pier, featuring motion seat technology, a 65-foot spherical screen, and a soaring musical score enhanced by scents and mists that make Chicago's skyline and lakefront feel vividly real. Details

The Chicago Explorer Pass by Go City is an affordable and convenient way to see the best of Chicago. Choose from over 30 top attractions, including Skydeck Chicago, Adler Planetarium, and Field Museum. Enjoy flexibility and savings as you explore at your own pace. Perfect for travelers looking to see more while spending less! Details

Join the Shoreline Architecture River Cruise from Michigan Avenue and witness the city’s incredible architecture and engineering marvels from the Chicago River! Cruise past over 40 iconic buildings, from the majestic John Hancock Center to the historic Wrigley Building, as your expert guide shares the history of the buildings, their architects and engineers. Details

Visit Medieval Torture Museum Chicago and discover the most extensive Middle Ages torture exhibits in the U.S. Located in the Chicago Loop, explore the interactive museum’s elaborate torture devices and realistic execution depictions that are not for the faint of heart! Do you have the courage to endure a visit to the horrifying evidence of human cruelty? Details

Discover the Windy City's dark history with Chicago Crime Tours. This 1.5 to 2-hour experience takes you to infamous crime scenes like the Biograph Theatre, Clark Street Bridge, and Holy Name Cathedral. Hear gripping tales of Al Capone, John Dillinger, Thomas "Terrible Tommy" O'Connor, and more—all from the comfort of a climate-controlled sightseeing bus. Details

Step into the spotlight with The Chicago Theatre Tour! Marvel at the French Baroque-style architecture, walk the iconic stage, and explore behind-the-scenes areas where entertainment legends like Frank Sinatra and Dolly Parton once stood. From the grand lobby to the Wurlitzer organ, every corner tells a story of Chicago's rich cultural history. Details

Take in Chicago’s skyline from an open-top double-decker bus. Big Bus Tours Chicago makes sightseeing effortless with a hop-on, hop-off service. See famous landmarks like Millennium Park, Willis Tower, and Navy Pier while learning from insightful commentary. Ride at your own pace, capturing stunning views with convenient stops near top attractions. Details

Discover as many sites as you can with the All-Inclusive Chicago Pass by Go City. With access to over 40 attractions, you can enjoy a variety of experiences for guests of all ages and interests, including museum admission, theater tours, and sightseeing trips. Save money and plan your adventure through Chicago’s urban jungle with this one-of-a-kind passport! Details

Located just minutes from the Lincoln Park Conservatory and Old Town Triangle, iFLY Indoor Skydiving Chicago Lincoln Park offers the rush of free-falling in a safe and controlled environment—no airplane or parachute needed. Whether you are a first-timer or a seasoned flyer, expert instructors will guide you through an unforgettable adventure. Come fly today! Details

Unleash your imagination at LEGOLAND Discovery Center Chicago, where interactive exhibits, themed rides, and millions of LEGO bricks await. Explore MINILAND®, build and race creations, and enjoy 4D cinema adventures—perfect family fun for LEGO fans of all ages. Details

Located minutes from The Morton Arboretum and Arrowhead Country Club, iFLY Naperville offers the ultimate indoor skydiving experience for adventurers of all ages. Soar in a state-of-the-art wind tunnel with expert instructors guiding each flight. No experience necessary—just bring your sense of adventure and prepare for a flight experience of a lifetime. Details

Just minutes from O’Hare International Airport and Fashion Outlets of Chicago, iFLY Rosemont offers a thrilling indoor skydiving experience for first-timers and seasoned pros alike. Enjoy a 1.5-hour flying experience in a state-of-the-art vertical wind tunnel, no parachute needed. Let your dreams take flight at iFLY Indoor Skydiving - Chicago Rosemont! Details

This award-winning Chicago bike tour takes you through vibrant neighborhoods and along the scenic Lakefront Trail. Explore Lincoln Park, Old Town, and the Gold Coast with a local guide. Bikes and helmets are included, with photo stops at some of the city's most iconic views. Details

In the heart of downtown Chicago, the Writers Museum on Michigan Avenue walks you through centuries of American history and culture from the writers' perspective. The American Writers Museum-Chicago is the only museum devoted to diverse US writers and writings, with fun multi-sensory exhibits to celebrate the past and promote the future of American literature! Details

Step aboard the Shoreline Architecture River Cruise from Navy Pier and discover the magic of the Windy City’s architectural wonders! Glide past over 40 iconic buildings, from the majestic John Hancock Center to the historic Wrigley Building, as your expert guide provides detailed descriptions. Kids age 2 and under are free, and the tour is dog-friendly, too! Details

Bypass the wait with a skip-the-line guided tour of the Art Institute of Chicago. Immerse yourself in a world-class collection, featuring Impressionist and modern masterpieces, such as Sunday on La Grande Jatte by Georges Seurat and Nighthawks by Edward Hopper. Let an expert guide reveal the stories behind both iconic artworks and lesser-known treasures. Details

Hop on your bike and get ready for a tasty tour through Chicago’s most diverse and delicious neighborhoods. You’ll stop at local eateries loved by locals all while learning about Chicago’s history, notable landmarks, and restaurants. This four-hour tour includes all food and beverages, along with bikes to ride if you don’t have one. Details

Sail with your pup on the 90-minute, dog-friendly Canine Cruise through the Chicago River and Lake Michigan. Take in skyline views, live architectural commentary, and thoughtful amenities for both dogs and their humans. It's one of the most unique and pet-friendly things to do in Chicago. Details

Hop aboard the Chicago fireworks cruise on Lake Michigan and watch the night sky light up in 3D. Departing from the Chicago Riverwalk, take in the panoramic skyline views from the open-air deck with lively narration on the way to the Harbor Lock. Then, enjoy a spectacular fireworks show enhanced with complimentary 3D glasses and synchronized music. Details

Take in sweeping views of Chicago’s skyline from the water on the Chicago by Night Cruise. As you glide along the Chicago River and the Lake Michigan shoreline, a knowledgeable guide shares insights into the city’s architecture, history, and cultural landmarks. Watch as the skyline lights up at dusk, offering a striking and memorable perspective of the city. Details

Sample some of Chicago's famous dishes on the Chicago Favorites Ultimate Food & Walking Tour. Indulge in deep-dish pizza, the original chocolate brownie, and local craft beers. Visit some of the most renowned restaurants and bars in the city. Along the way, you’ll come across Chicago’s landmarks, well-known neighborhoods, and historic spots. Details

Indulge in a premier Chicago dinner cruise aboard Odyssey Lake Michigan. Departing from Navy Pier, pass by iconic landmarks such as Willis Tower, Adler Planetarium, and more. Whether celebrating a special occasion or simply looking for a unique dining experience, this dinner cruise in Chicago offers an unforgettable evening of elegance and fine dining. Details

Celebrate the city’s vibrant Chinese heritage on a Chinatown food tour in Chicago, savoring dim sum, noodles, and regional specialties. Discover the neighborhood’s rich cultural history while sampling local favorites at hidden-gem restaurants in Chinatown Square and along Wentworth Avenue. Details

Explore Chicago's iconic landmarks on a three-hour guided bike tour with Bobby's Bike Hike. Enjoy a leisurely nine-mile ride along the Lakefront Trail, visiting sites like Museum Campus, Millennium Park, and more. Perfect for all fitness levels. Details

Explore Chicago’s skyline and landmarks on a 90-minute guided river and lake cruise aboard the First Lady. Enjoy expert commentary on architectural icons like Willis Tower, Tribune Tower, and the Wrigley Building. This family-friendly cruise offers stunning views and insights into the city’s rich history and design legacy. Details

Wendella's Chicago Lake and River Architecture Tour offers expert narration and skyline views from both the river and Lake Michigan. Cruise past more than 50 landmarks along the river, then pass through the Chicago Lock into Lake Michigan for panoramic views stretching from Navy Pier to Grant Park. Details

Step into the lives of Chicago’s most notorious criminals as you embark on this nighttime tour. From the comfort of an air-conditioned bus, you’ll encounter iconic crime scenes and historic bars. Drinks are not included. On this 2.5-hour luxury bus tour through the streets of Chicago, you’ll learn about everything from the legendary Al Capone to the St. Valentine’s Day Massacre. Details

Experience the breathtaking Chicago Skyline on a 45-minute Lake Michigan cruise departing from Navy Pier. Enjoy stunning views of the city’s iconic landmarks and skyscrapers such as The Chicago Harbor Lighthouse and Willis Tower, and informative pre-recorded commentary about the history of Chicago’s famous buildings. Don't forget your camera! Details

Set sail on a Chicago lunch cruise for a casual day out on Lake Michigan aboard the Spirit of Chicago. Departing from the iconic Navy Pier, the cruise will pass by iconic landmarks such as the Willis Tower and Adler Planetarium. Feast on a delectable chef-prepared lunch buffet while enjoying stunning views of the Chicago skyline and onboard entertainment. Details

See Chicago from the ground up and from way up high on this private Chicago walking tour! Discover more about The Windy City while taking advantage of all the city has to offer– including the expansive trails of Millennium Park, the opulent stores on Magnificent Mile, unique art and architecture that defines the city, and a stunning view of the Chicago skyline. Details