Things to Do in Chicago

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

Make your time in Chicago into a piece of art with this private photoshoot that includes the rental of a stunning flying dress. Share your glamorous moment with ease with 30 digital photos.

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!

With our travel insurance, you can travel with peace of mind and focus solely on unwinding and enjoying your holiday. Don't let anything spoil your trip!

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

Experience the excitement of a live Chicago White Sox game at Guaranteed Rate Field. Enjoy the energy of a true Chicago sports crowd and the smell of ballpark favorites.

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment. What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

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

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.

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.

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 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!

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.

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.

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

Explore one of the largest science museums in the world with a ticket to Griffin Museum of Science and Industry in Chicago. See science, technology, and engineering brought to life through exhibits.

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.

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!

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

Join us for an exhilarating urban art workshop in Chicago and delve into the dynamic world of street art, all while sipping on your favorite beverages (BYOB for those 21+).

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!

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.

• 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.

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.

Cruise the Chicago River or Lake Michigan on a tiki-themed boat with a full bar. Enjoy tropical cocktails, beers, and wines as you take in the city’s skyline and historic landmarks.

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

Book your ticket for this Premier Plus Architectural Lunch Cruise in Chicago. Sit back and relax during a narrated tour and enjoy chef-prepared plated menus.

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

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.

With the Go City: Chicago Explorer Pass, you’ll get access to 2 to 7 of the city’s attractions. With the Essentials Pass, you’ll visit 3 attractions.

• Enjoy a 2.5–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 and take in the Lake Michigan views by the river’s glow.
• Bring the whole family and enjoy free admission for infants under two.
• Creative cocktails, wine, and beer are available on your cruise for purchase to add to your cruise, ideal for celebrations or a special night out.

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic 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 .

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!

• 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.

Explore the world's most remarkable art pieces at the Art Institute of Chicago with your personal self-guided audio tour.

Unlock the secrets of Chicago's most-photographed venue with The Chicago Theatre Tour Experience. Marvel at the grandiose architecture and walk in the footsteps of legends on this exclusive tour.

This is the only tour in Chicago that explores the movie "Ferris Bueller's Day Off" from the perspective of art. It's also the only walking tour that immerses you in the actual artwork featured in the 1986 American teen film. Over the course of the tour, you'll visit 3 floors of the museum, see 16 pieces of art, and leave with an appreciation of the works, their relationship to characters, and their placement in the camera's frame. ⚠️ NOTE: Admission to the Art Institute of Chicago is NOT included in the public walking tour. The tour starts under the stairs in the *Modern Wing* of the Art Institute, Griffin Court. Guests must digitally sign a general waiver of liability. Guardians must sign waivers for children under the age of 18.

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!

• 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!