Things to Do in Chicago, Illinois

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

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

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

Experience the Windy City’s iconic sights with the Hop-On Hop-Off Chicago Big Bus and explore the city at your own pace. Enjoy panoramic top-deck views of iconic skyscrapers and Lake Michigan, and hop off to explore the Magnificent Mile, Field Museum, Adler Planetarium, and more. Download the free Big Bus app for routes and real-time tracking. Details

Discover as many sites as you can with the All-Inclusive Chicago Pass by Go City. With access to over 30 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

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

Discover a world of creativity, excitement and fun at LEGOLAND® Discovery Center Chicago! Build, play and learn with your family and friends in Chicago’s only two-story LEGO ultimate experience. With 12+ attractions, including a 4D cinema and a jaw-dropping Miniland Chicago cityscape, there’s something for everyone at LEGOLAND in Schaumburg. 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

To say that the bald, brilliant and hilarious blue men march to the beat of their own drum is an understatement. This loud, bright and over-the-top show filled with technology, sensory theatrics, comedy, music and hijinks is the perfect form of entertainment. To truly understand the hype over the Blue Man Group in Chicago, you have to see it for yourself! 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

Join the Chicago walking tours and sample the Windy City’s iconic food, including deep-dish pizza, the original chocolate brownie, and local craft beers. These walking tours bring you around to 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

Head out on the Chicago River Dinner Cruise aboard the glass-enclosed Odyssey Chicago River dining vessel to enjoy the heart of Chicago from a unique perspective! Savor a delicious 3-course plated dinner and iconic architectural landmarks such as the Willis Tower, DuSable Bridge, and Merchandise Mart, all beautifully illuminated against the night sky. 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

Experience one of the world's greatest museums with an expert tour guide! This skip-the-line guided tour explores major artworks and hidden gems from the expansive Art Institute of Chicago collection, which can be overwhelming to explore on your own. The tour begins half an hour before the museum opens allowing you to stroll among the galleries at a leisurely pace. 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

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

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

Embark the bike tour that’s been recognized by National Geographic, USA Today, and the Associated Press. This leisurely bike tour of Chicago’s Near North Side neighborhoods will captivate you as you view the skyscrapers, visit Lincoln Park, and bike along the Lakefront Trail. Bring a camera along for the ride so you can capture these memories for a lifetime. 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

For authentic cuisine with a rich history, embark on a Chinatown food and walking tour with Bobby’s Bike Hike, America’s longest running city bike tour company. As you stroll through Chinatown’s neighborhoods on this 2.5-hour tour, you’ll sample Cantonese dim sum and tea, try Portuguese-Chinese baked goods, and so much more. Plus, you’ll learn about the history behind the cuisine and culture. Details

Operated by Bobby’s Bike Hike, America’s longest running city bicycle tour company, this 2.5-hour bike tour brings you around to Chicago’s greatest landmarks and sights. You’ll see everything from Museum Campus to Cloud Gate, and Grant Park to Buckingham Fountain. If you’re looking to maximize your time in Chicago while staying active, this is the perfect tour for your trip. Details

There’s nothing more magical than Chicago during the holiday season. Embark on a walking tour through Chicago’s most festive neighborhoods and restaurants. Sample the city’s best pizza while marveling at sights and decorations along the Magnificent Mile, strolling through Christkindlmarket, and sipping on the Windy City’s best craft beer. It’ll be a holiday season unlike any other! 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

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

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