Things to Do in Chicago

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

Enjoy views of Chicago's riverfront architecture as you cruise along the Chicago River. Admire the scenery from the ship's glass-enclosed dining area. Choose between a brunch, lunch, or dinner cruise.

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!

Interact with installations and explore emotional projections

Learn about the dark past of deception and corruption on this tour of Chicago's historic crimes and mysteries! A chilling experience awaits.

• Get timed entry and head straight up to Skydeck Chicago on the 103rd floor of Willis Tower for sweeping, unobstructed views of Chicago and up to four neighboring states.
• Step onto The Ledge—glass-floored balconies that extend 4.3 feet outside the tower—and look straight down from 1,353 feet above the ground, if you dare!
• Explore the newly expanded Chicago Experience, an interactive museum featuring digital exhibits that celebrate the city’s culture, history, and neighborhoods.
• Enjoy incredible photo ops from day to night, with prime views of the skyline, Lake Michigan, and iconic landmarks like Navy Pier and Wrigley Field.
• Ride one of the fastest elevators in the U.S. and reach the top in just 60 seconds—perfect for thrill-seekers, families, and first-time visitors alike.

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

Explore the EmotionAir exhibition in Chicago with this entry ticket. Discover the relationship between art and emotions through inflatable art, interactive installations, and projections.

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.

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

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.

• Sail through the heart of Chicago on 45-min guided architecture cruise, enjoying expert commentary, gorgeous skyline views, and onboard refreshments.
• Glide along all three branches of the Chicago River including the North Branch, the Main Stem, and the South Branch, as your guide shares fascinating insights into the city's 130-year architectural evolution.
• Capture unobstructed views of Chicago’s iconic skyscrapers from the open-air upper deck, offering perfect photo opportunities of the cityscape.
• Spot famous buildings like the Tribune Tower, Apple Store, AMA Building and the Wrigley Building.

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

Discover Chicago with a unique tea tour. Sip gourmet teas, enjoy light bites, and soak up city views from a floral-themed double-decker bus with live entertainment.

Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy bars, sites of real life mob shootouts, and haunted tragedies that shape the city's legacy. This walking tour blends ghost stories, true crime history, and architectural landmarks to reveal the beauty and horror from one of America's most famous time periods, right where it happened. You'll gain special access to architectural interiors tied to famous history, as you are led by a trained historian tour guide through these famous sites. Learn where Chicago's history still whispers after dark!

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

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

• Enjoy a 90-min guided architecture cruise on the Chicago River, complete with expert commentary, skip-the-line access, and onboard refreshments.
• Sail through the main river and its north and south branches, taking in Chicago’s skyline from an open-air deck or a climate-controlled interior.
• The tour highlights 130 years of Chicago’s architectural history as expert guides share fascinating stories behind the city's most famous and innovative buildings.

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

Experience Chicago’s legendary architecture from the best seat in the house: the river. Enjoy a comprehensive tour with a live fun guide as you navigate through the heart of the city covering all 3 branches of the Chicago River.

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.

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

The Go City: Chicago Explorer Pass offers access to 2, 3, 4, 5, 6, or 7 of Chicago’s attractions. Save up to 50% off prices!

• Rise above the ordinary, and see Chicago from a soaring 1,000-foot-high perspective that will take your breath away.
• The 3D mural on the deck creates an illusion of cloud-walking that's a joy for the 'gram.
• Skip the long snaking lines with your ticket and head straight to the observation deck.
• Unwind at Cloud Bar and soak up iconic Chicago views while sipping on locally brewed Moody Tongue beer, an unbeatable combo.
• Fun Fact: The elevators at 360 Chicago are among the fastest in North America, zipping you to the top in no time!

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

Connect with your curiosity and explore Chicago with an immersive Flyover ticket. Experience the city's highlights from this perspective, as your journey transports you over iconic destinations.

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!

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

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!

• Enjoy a 2.5–3 hour Chicago River cruise aboard the Odyssey, complete with a gourmet plated dinner and live, curated entertainment for an unforgettable evening on the water.
• Marvel at Chicago’s iconic skyline and architectural masterpieces from a climate-controlled interior deck, with guaranteed seating and unlimited coffee, hot tea, iced tea and water.
• Elevate the evening with a window-table upgrade or opt for the fireworks cruise to capture Navy Pier’s spectacular fireworks framed by the river’s glow.
• Bring the whole family; infants under two cruise free, while creative cocktails, wine and beer await at the cash bar, ideal for celebrations or a special night out.

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

See Chicago from above on a thrilling helicopter flight over the city’s most iconic landmarks. Enjoy stunning skyline and lakefront views with a professional pilot guiding your journey.

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.

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

Visit the most iconic landmarks at your own pace with the Chicago Tourist Bus. The most comfortable and convenient way to explore the Windy City!

• Plan your Chicago itinerary without worrying about arranging travel with this 24/48/72-hour hop-on hop-off bus tour, hopping off unlimited times.
• Tour Chicago on the Red Loop with 11 great stops and buses every 30-45 minutes, letting you hop off and explore without missing a beat on your journey.
• Choose an upgrade to pick one from four Vox app self-guided walking tours that reveal Chicago’s hidden alleys, sights, and more with local stories!
• Board a double-decker bus, admire Chicago’s 360° skyline, and enjoy English or Spanish audio guides that share stories behind the iconic landmarks.
• Tour Chicago with front-row views of Millennium Park, Magnificent Mile, Willis Tower, and Hancock Tower for a line-up of the city’s legendary sights.

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

Enjoy a fully immersive experience at the Museum of Ice Cream, delivering joy and entertainment for the whole family. Savor signature ice cream flavors and sweet treats as you explore the museum.

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.

Get a bird's eye view over the Magnificent Mile with 360 Chicago tickets

This entrance to the Chicago Museum of Ice Cream really is a sweet deal! You can indulge your inner child and spend the day tasting delicious ice creams.

• Discover new artists, latest additions, timeless masterpieces, and hidden gems in one of the world’s most celebrated art museums.
• Your admission ticket includes day-long, flexible entry to the Art Institute of Chicago, all exhibits and works inside, and complimentary daily tours.
• View works that span generations, art movements, and continents, along with rotating exhibits from upcoming and celebrated artists.
• Enjoy free daily tours and dive deeper into the stories behind world-famous masterpieces.
• Their collection includes classics such as The Great Wave by Hokusai, Nighthawks by Hopper, Self Portrait by Van Gogh, The Beach at Sainte-Adresse by Monet, and more.

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

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago Fire TV Show Set Tour. Visit the actual filming locations where the show comes to life.

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 .

Save up to 29% on combined admission to your choice of three top attractions

Discover the best of Chicago's modern and green spaces on this private guided tour by car. See the city's most emblematic places with your own tour guide!

• Buckle up! The ride to the 94th floor in one of North America's fastest elevators is just the start of your thrilling adventure.
• Along with scenic vistas, your ticket also includes skip-the-line access. No waiting around, just straight to the top for uninterrupted city views.
• Discover Chicago's diverse neighbourhoods at 360 Chicago's interactive exhibit, and watch '3 of 77' for immersive insights beyond downtown.
• Not just a view, the CloudBar serves up iconic local snacks like Garrett's popcorn and neighborhood-inspired cocktails.
• Fun fact: 'Travel & Leisure Magazine' voted 360 Chicago for having one of the best views in America. You're about to see why!

Learn what tragic story is covered by Chicago River's waters, explore the most haunted sites and buildings, hear about rise and fall of the most infamous gangsters.

Explore Chicago on a Crime and Mob Bus Tour. Escape into the city's underworld and learn about infamous gangsters and mobsters like Al Capone and John Dillinger.