Top Chicago Culture in 2026 - page 2

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important cultural and historic destinations, including Jackson Park, the Obama Presidential Center campus, and the Griffin Museum of Science & Industry. Enjoy an easy ride south without arranging taxis, rideshares, or public transit connections. The shuttle first stops near the Obama Presidential Center and Jackson Park, giving you access to one of Chicago’s most historic lakefront spaces. Explore the area at your own pace, take photos, or continue your visit independently. The route also serves the Griffin Museum of Science & Industry, one of Chicago’s most popular attractions and one of the largest science museums in the world. This is a great option for travelers who want a simple, affordable way to visit Chicago’s South Side highlights from downtown. Choose a one-way transfer or an all-day ticket for added flexibility.

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s most influential neighborhoods. Guests will enjoy curated tastings from locally owned Black restaurants while learning about the people, businesses, and historical moments that helped shape Chicago’s Black cultural landscape. Along the route, we visit significant landmarks, including the site where Barack and Michelle Obama’s love story began, historic community gathering spaces, public art, and locations connected to the neighborhood’s rich legacy of entrepreneurship, music, education, and civil rights. Unlike traditional food tours that focus primarily on dining, this experience connects each tasting to the larger story of the community, providing travelers with insider knowledge and meaningful cultural context.

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Discover the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

The Sloomooverse combines delicious scents (birthday cake, fresh berries, cotton candy), sounds that energize as well as soothe, an invigorating palette, and a feast of visual and tactile wonders. Plus, you’ll design your dream slime at our DIY Bar. Over 4,320,000 unique combinations! Play, connect, enjoy!

Discover one of the Windy City’s most spooky, gruesome destinations when you book advance tickets to the Medieval Torture Museum. Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge. Book tickets before you travel for a seamless visiting experience, and make use of an audio guide and included ghost-hunting app.

Enter a land of sugar and adventure with admission to Chicago’s Museum of Ice Cream. Immerse yourself in a vibrant world of interactive exhibits, including sprinkle-filled pools, whimsical selfie spots, and exclusive ice cream sampling stations offering seasonal flavors. Whether you’re an art lover or a dessert enthusiast, this playful, family-friendly experience promises fun and memories for all. Avoid disappointment by booking your preferred time.

Discover a dark, spooky side of Chicago that most tours miss on this adults-only ghost walking tour. Keep an eye out for sinister specters and ghastly ghouls as you explore abandoned buildings and shadowy alleyways near some of Chicago’s most popular landmarks, including the Chicago Theatre, Millennium Park, and the Art Institute of Chicago.

Discover one of downtown Chicago's highlight museums, and explore the works of leading artists across myriad media and genres, when you book tickets to the Museum of Contemporary Art. Choose from multiple entry times throughout the day, make your own way to the museum, and get ready to explore. Exhibitions are ever-changing, but you can expect to see works by artists the likes of Kara Walker, Jasper Johns, Cindy Sherman, and beyond.

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

Bored of traditional walking tours? Try an experience that mixes sightseeing with an engaging game in this murder mystery tour through Chicago. Play as a detective and a suspect as you wander through various neighborhoods and see the city. Learn about the real legends and crimes of Chicago while you try to solve a murder.

One of the easiest and most affordable ways to explore Chicago's top attractions is through a Chicago Explorer Pass by Go City. Save money compared to buying individual attraction tickets, and create your own sightseeing itinerary by choosing from among more than 35 top sites, including the Skydeck Chicago, a sightseeing cruise, a hop-on hop-off Big Bus tour, Navy Pier, and more.

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.