Things to Do in Chicago

See amazing animals, incredible views, fascinating science, world-class art, and more with Chicago CityPASS tickets.

Discover Chicago’s iconic architecture on a half-day tour of skyscrapers, historic bridges, and public spaces with expert guidance and a panoramic skyline finale.

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!

Get some of the best views of Chicago from this circular skyline spinner

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Enjoy a 90-minute comprehensive boat cruise of Chicago's legendary architectural wonders from the best seat in the house, the river.

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. Toast the end of the day with a glass of wine, ice-cold beer or hand-crafted cocktail.

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

A family-friendly introduction to Chicago's magnificent architecture

Get the most stunning views of Chicago from the 360 Chicago Observation Deck, at the absolute best price! A must if you're in Chicago.

Admire Chicago from the 94th floor. Learn about Chicago's history and architecture and discover the CloudWalk and the 3D mural by Nate Baranowski.

Explore downtown Chicago through its underground passageways, known as "The Pedway," accessing beautiful interiors from both above ground and below, with secrets along the way, on a walking tour.

Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then shows you how the very same streets turned into movie magic. Walk the same corners seen in 'The Untouchables' and 'Public Enemies,' and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both. Your guides aren’t just storytellers—they’re trained true crime historians, film buffs, and Chicago insiders who bring every scene to life. Step inside exclusive interiors where real mobsters plotted and Hollywood crews once brought the Windy City to the Silver Screen. We take you deeper into the story than any other tour can. Expect vivid tales, insider trivia, and behind-the-scenes stories that make Chicago’s gangster past feel as real as the movies it inspired.

Interact with installations and explore emotional projections

Climb to the highest observation deck in the United States by booking your tickets for Skydeck Chicago. You'll be on the 103rd floor of the famous Willis Tower!

Discover Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire.

Dine aboard a yacht and enjoy an extensive buffet meal while cruising down Lake Michigan. Dance to the live DJ or play exciting games like giant Jenga and shuffleboard as you enjoy Chicago's sights.

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Get a bird's eye view over the Magnificent Mile

Discover Chicago's iconic landmarks on a free walking tour, including a scenic park on Lake Michigan. Explore hidden gems in the Windy City!

• Enjoy a 2.5-hour cruise on the Chicago River and Lake Michigan with a gourmet dinner and live entertainment onboard.
• Relax in a climate-controlled interior deck while enjoying scenic views of Chicago’s skyline and architecture.
• Enjoy a chef-prepared meal as you take in the breathtaking views of Chicago's skyline and iconic architecture.
• Live curated entertainment, along with an onboard bar with beverages available for purchase, enhances your dining experience, making it perfect for special occasions.
• Choose between a Chicago River cruise with a plated gourmet dinner, a Lake Michigan cruise with a plated gourmet dinner, or a Lake Michigan cruise with a buffet dinner.

Book your architecture river cruise in Spanish and pass the most iconic buildings along the Chicago River!

Cruise along the Chicago River on a boat tour and discover hidden architectural gems among the city’s renowned landmarks, with live narration.

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!

Rocket to the 103rd floor and enjoy spectacular views of the Windy City

The Windy City has a wealth of attractions, museums and galleries you'll fall in love with. Discover them all with the Chicago CityPASS®.

• Set sail from Michigan Avenue or Navy Pier in the heart of Chicago for an insightful 75-minute architecture river cruise.
• Board a vessel offering unparalleled views of over 40 landmarks, including the neo-Gothic Tribune Tower and the 398-foot Wrigley Building.
• The cruise features live commentary from a knowledgeable guide, vividly depicting Chicago's architectural history and evolution.
• Choose the preferred language for your tour with expert narration offered in both English and Spanish for tours departing from Michigan Avenue.
• Did you know? The Tribune Tower has fragments of famous world structures like the Great Wall of China and the Taj Mahal embedded in its walls.

Welcome to sweet home Chicago! Discover this remarkable city with your very own CityPASS and see top highlights.

Discover thrills at Six Flags Great America in Gurnee, the “Thrill Capital of the Midwest.” Enjoy world-class coasters, spectacular shows, and three children’s areas between Chicago and Milwaukee.

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain.   Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.

Hang out with Picasso, Dalí, Monet, Renoir, Warhol, and many more!

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• Soak in panoramic views of Chicago’s skyline and iconic architecture on your 2.5-hour Lake Michigan dinner cruise.
• Enjoy a chef-prepared three-course dinner, unlimited coffee, tea, and a guaranteed table from the comfort of a climate-controlled deck.
• Infants under two cruise free, along with accommodations for any dietary restrictions, making this a welcoming cruise for all.
• A DJ curates the evening’s ambiance, adding a lively energy as you cruise past Chicago’s illuminated skyline.
• Creative cocktails and additional beverages are available for purchase on board, so that you get to customize your experience.

Enjoy a charming and exciting night out in Chicago with dinner, music and sightseeing aboard the Chicago Premier Dinner Cruise.

It's Game On! at the Chicago Sports Museum. Explore the city's rich sports history, test your skills in hands-on exhibits, and view rare sports memorabilia at Chicago's playground for sports fans!

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, we’ll visit a rooftop spot for skyline views, cross the scenic DuSable Bridge, and stop by the elegant Wrigley Building - all perfect for beautiful photos. Along the way, I’ll guide you with natural poses and creative ideas, helping you feel relaxed and confident. By the end of this walk, you’ll not only have a beautiful photo gallery - you’ll have also visited many of the MUST-SEE places in downtown Chicago.

Explore an endless array of artifacts in one of Chicago's best museums

Enjoy the main tourist attractions around the windy city with the Go City: Chicago All-Inclusive Pass. Choose between a 1, 2, 3 or 5 consecutive day pass.

Enjoy a relaxed atmosphere with music and a view of the Chicago skyline and try different mouthwatering meal options on your unique cruise.

Hop aboard the Odyssey Lake Michigan, a yacht designed for the ultimate viewing of Chicago's sights, and savor a gourmet 3-course lunch or dinner while enjoying the view from the water.

Take a tour of Chicago's Pedway system (a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other) and enjoy seasonal holiday decorations and sights along the way. Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling, the "Great Tree" in the Walnut Room and the store’s decorated holiday windows. We return to the Pedway and follow it to Civic Center Plaza for a visit to the Christkindlmarket, an authentic European holiday market. We return to the Pedway for a visit to City Hall followed by a short walk to a nearby L station. A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s lion statues, and Millennium Park to view the famous Cloud Gate sculpture, aka, The Bean and the city's holiday tree .

You won't believe your eyes at the Museum of Illusions

Cruising down the Chicago River is one of the greatest ways to get to know the iconic city and discover how it became the birthplace of the skyscraper.

• Discover Chicago's architectural wonders on a guided cruise along the Chicago River with live commentary.
• As you set sail, enjoy insights from your local guide on Chicago's architectural heritage.
• Take the cruise to gain a deeper appreciation of Chicago's legacy by exploring its most famous landmarks from a unique vantage point on the river.
• See over 50 landmarks, including the Wrigley Building, Chicago Riverwalk, Michigan Avenue Bridge, and Willis Tower, offering a blend of educational insights and comfort.
• Choose to upgrade from a 45-min cruise to a 60-min or a 90-min cruise for a more in-depth exploration of Chicago's history.

Get your Go City Explorer Pass, pick 2, 3, 4, 5, 6 or 7 attractions of your choice in Chicago, scan your pass at the entrance and you're in. It's easy and convenient!

One easy pass to access three Chicago highlights. Choose from jaw-dropping observation decks, river cruises, fascinating museums, fun museums and more - and save big vs. buying tickets individually.