Top Chicago Arts & Design in 2026

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).

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.

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn fascinating stories about the city’s history and culture. At each stop, professional photos will be taken of you or your group, allowing you to take home original digital images that capture your adventure in the Windy City. - Visit five picturesque locations for memorable photos - Enjoy breathtaking skyline views throughout the tour - Receive original digital photos after the tour to keep the memories alive - Perfect for couples, families, or anyone wanting to explore Chicago through photography

Travel through architectural history on this express, small-group walking tour, which covers Chicago's most famous buildings in chronological order (and which is speedy enough to cater to the most time-pressed travelers). With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth commentary on Chicago's architectural history; you'll learn about each building, and will have plenty of chances to stop for photos.

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.

Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 2017, and is one of the city’s newest highlight institutions. Guarantee your admission, and prevent any travel hassles, by securing your tickets in advance. Once inside, you’ll have time to explore at your own pace.

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mile and Chicago River, where Tribune Tower, the Wrigley Building, and DuSable Bridge introduce the city's skyline. Continue downtown to see Willis Tower and the Art Deco Chicago Board of Trade Building, with pass-by views of Marina City, Merchandise Mart, the Civic Opera House. Enjoy a 20-minute stop at Millennium Park to see Cloud Gate (The Bean), followed by a separate 10-minute stop at Clarence F. Buckingham Fountain in Grant Park when operating, typically May through October. Stop for a photo at the historic Route 66 Begin Sign and pass the Art Institute of Chicago before finishing at Museum Campus. Admire views of the Chicago skyline across Lake Michigan, with exterior views of the Field Museum, Adler Planetarium, and Shedd Aquarium. This compact itinerary combines Chicago's signature sights and photo stops in one outing.

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk on this private, self-led smartphone walking tour. Upon booking, download the app and receive a password to access your tour; once it’s on your phone, it is valid forever. Set off at a time that works best for you: see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.

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.

Explore the Loop's famous architecture—and learn insider facts and stories that you wouldn't encounter if exploring alone—on this small-group walking tour. Led by your Chicago Architecture Center–certified guide, you'll discover some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. Admire the Rookery building, see the Marquette building, and much more, all while soaking up the city's ineffable energy.

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

Being short on time in Chicago doesn’t mean you need to rush your sightseeing. This combo tour helps you admire the Windy City from two perspectives—on land during a hop-on hop-off bus tour and from above at the 360 CHICAGO Observation Deck. Skip the stress of booking separate tickets and explore at your own pace.

With so many of Chicago’s most popular landmarks so spread out, it can be tough to see them all on foot or by public transport. On this private driving tour, listen to facts about the city as you’re delivered to Wrigley Field, Millennium Park, the Chicago Cultural Center, and much more.

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

Enjoy a budget-friendly way to explore Chicago—and see the sights that interest you most, all without following a large tour group around—with this cost-savings Chicago Attractions Pass. Enjoy discounts of up to 50% on an array of top Chicago attractions, including the 360 Chicago and SkyDeck observation decks, the Field Museum, Chicago River cruises, and more. Four different pass durations are available when booking.

Follow a self-guided adventure during this special smartphone-based game in Chicago’s Millennium Park. Learn about the city’s iconic works of art and architecture while enjoying views of Lake Michigan and the Chicago skyline. Play anytime you’d like, seven days a week, with no data or Wi-Fi needed.

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history, iconic landmarks, hidden gems, and must-see photo opportunities. From legendary deep-dish pizza and historic jazz venues to world-famous architecture and vibrant local districts, the local guides provide personalized recommendations for every type of traveler. No need to spend hours planning your trip—this tour is designed to give you the insights, stories, and local knowledge needed to make your Chicago experience unforgettable. * Learn about the essentials of Chicago * Get tailored recommendations from local guides * Take amazing photos at iconic and hidden-gem locations * Get familiar with the city's history, culture, and neighborhoods

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired European styles to bold American Art Deco and Modernist innovations to today’s Contemporary designs that continue to set the pace for world-leading architecture. As you journey through Chicago’s spectacular skyscraper canyons and stunning interiors, you’ll see how economics, technology, creativity, and gritty determination shaped Chicago’s ever-evolving skyline. Whether you’re a visitor or you’re a Chicagoan who has never explored the architectural masterpieces you see every day, join us today on this enlightening adventure.

Lots of tours help you explore Chicago’s historic streets, but most avoid the grittier details that have helped shape the city over the decades. But this small-group walking tour doesn’t shy away from the gruesome details. Listen to tales of gangsters, restless spirits, and local disasters as you navigate some of Chicago’s most popular landmarks.

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

There’s so much amazing architecture in Chicago but wandering around alone can leave you overwhelmed, and unsure of what you’re looking at. Check out some of Chicago's most important new buildings on an architecture walking tour. The tour is focused on the area around the Chicago Architecture Center (CAC), beside the Chicago River, so you don’t get overwhelmed exploring the whole city. Admission to the CAC’s galleries is also included.

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.