Top Chicago Arts & Design

Fit far more of Chicago’s most popular landmarks into your trip than you could exploring solo, thanks to this small-group minibus tour. Gaze into the mirrored surface of the Cloud Gate (the Bean), navigate the Magnificent Mile and the Chicago River, take in views of the Willis Tower, and much more.

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).

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.

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.

Experience360 by the Illinois Holocaust Museum memorializes the lives and stories of Holocaust victims and survivors in a way that guidebooks can’t match. With this admission pass, engage with holographic stories and virtual reality experiences, reflecting on the somber lessons taught by one of modern history’s most important and traumatic events.

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 Chicago architectural treasures—and immerse yourself in the Windy City's history—on this small-group walking tour. Your focus is the iconic stained glass pieces crafted and designed by the Tiffany Glass and Decorating Company. Following your guide from the Chicago Architecture Center, visit four late-19th-century landmarks that contain glass works by Louis Comfort Tiffany and his contemporaries. This in-depth, insider tour is a must-do for history and architecture fans.

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.

Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally led Pilsen walking tour offers an authentic, insider experience beyond typical Chicago sightseeing. - Pilsen-based experts with 40+ years of combined experience - Explore iconic sites like 16th Street murals, Thalia Hall, and local cultural landmarks - Official Pilsen tour partner of the Chicago History Museum - Bilingual tours available in English and Spanish - Multiple routes and flexible options, including walking, running, or biking tours -BOOKING: Please note the tour guide will contact you to schedule an exact time for your tour after you have completed the booking. There is no option to pick a start time.

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.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares insights into Wright’s life, ideas, and influence on modern architecture. Begin at the Frank Lloyd Wright Home & Studio, where he lived and developed many revolutionary designs. Continue through the Oak Park to admire beautifully preserved Prairie School homes and early residential works. Visit Unity Temple, one of Wright’s most celebrated modern religious buildings, then return toward Chicago to see The Rookery Building with its grand lobby and intricate design. Conclude at Robie House, a masterpiece of Prairie School architecture showcasing Wright’s signature horizontal lines and integration with the landscape. This flexible experience offers architecture enthusiasts a relaxed way to explore Wright’s legacy and the evolution of modern American design.

Save time upon arrival to the Chicago Architecture Center; with prepaid tickets in hand, you won't have to wait in line at the box office. Your tickets guarantee your admission even on sold-out days. You'll get access to all the exhibits and galleries, including the Chicago model exhibit and a selection of rotating architecture exhibits.

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

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.

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo walk, I’ll help you pose and feel comfortable while taking high-quality photos using iPhone, optimized for social media. You’ll receive about 50 digital photos, including 5 professionally color-edited images, delivered via a private online gallery. Please download your photos within 14 days after receiving access, as the gallery link will expire.

The vibrant Loop area is home to some of the city’s best preserved art deco buildings designed during the Roaring 20s—if you can spot them. With this small-group walking tour, your guide—an interior designer and historic architecture expert—points out about seven of the best art deco buildings, as well as other notable architectural highlights through the Financial District and parts of the North Michigan Avenue corridor.

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.

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.

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

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”

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot and by L train, and see the city’s most iconic landmarks like The Rookery Building, Chicago Cultural Center, First Arts Building, and more 19th and early 20th-century masterpieces. Be ready to see the City by the Lake from a new perspective and get to know it even closer as you stroll down its streets and travel by train. Enjoy the small-group experience and don’t miss a thing as you travel Discover the downtown and historical building together with your local knowledgeable guide Marvel at architectural landmarks of the City by the Lake and get to know the stories behind them Combine a walking tour with a train to see more landmarks and iconic sights on one tour.