Top Chicago Private and Luxury - page 8

See Chicago’s legendary Air & Water Show from the best seat in the city! Secure a VIP spot on a Lake Michigan cruise (or Skydeck viewing party) and watch the U.S. Air Force Thunderbirds, Golden Knights, and dazzling stunt pilots soar overhead. Enjoy premium amenities, from fast-track boarding to reserved seating, up-close views, and included food or drinks (per package). With unmatched photo ops and the sound of jets flying overhead, this is a must-see experience for locals and visitors alike—just in time for summer’s biggest Chicago festival. Book early; these shows always sell out fast.

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and more. See the theater from Public Enemies, Harold Washington Library from Ocean’s Eleven, the Chicago Board of Trade and Calder’s Flamingo from Ferris Bueller, iconic Blues Brothers spots, and Bruce Wayne’s penthouse and Harvey Dent’s office from The Dark Knight. Perfect for film buffs and Chicago enthusiasts alike.

Get ready to experience Chicago in full color with Tea Around Town. Step aboard our signature pink double-decker bus, beautifully adorned with vibrant wildflowers that bring a whimsical touch to the Windy City streets. Sip fine teas, enjoy delicious treats, and sing along with our entertainers as you journey past Chicago’s most iconic landmarks—from Millennium Park and the Magnificent Mile to the historic Riverwalk.

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating stories, insider insights, and exclusive information tailored to your interests.

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the Peggy Notebaert Nature Museum, the lush Lincoln Park Conservatory, and the vibrant Lincoln Park Zoo—curated into one dynamic, story-filled journey led by a knowledgeable local guide. You'll marvel at the butterflies in flight, wander through exotic gardens under glass, and encounter wildlife from around the world—all while uncovering the hidden history and surprising beauty of this beloved urban oasis. Whether you're a first-time visitor or a lifelong Chicagoan, this tour offers fresh insights, natural wonders, and photo-worthy moments at every turn. Book now and see why Lincoln Park is one of Chicago’s most treasured gems!

Embark on an exclusive journey through Chicago's storied past with a private tour unveiling the city's 1920s Art Deco and Art Moderne architectural wonders. Led by a knowledgeable local guide, delve into Chicago's pivotal role in shaping the global Art Deco movement, an era synonymous with innovation and elegance. Marvel at the intricate facades and lavish designs adorning the city's iconic buildings, each a testament to the opulence and creativity of the Jazz Age. Gain profound insights into the architectural evolution that defined Chicago's skyline, from the roaring twenties to the present day. This immersive experience promises a deep dive into the vibrant history and enduring legacy of Chicago's architectural heritage, offering a unique perspective on the city's rich cultural tapestry.

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.

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies you from Chicago to Los Angeles, transforming each stretch of road into an experience full of context, curiosities and stories that give meaning to the journey. You don’t just drive – you understand the landscapes, cities and small towns that marked the American dream. No schedules, no groups and no rush, just you, the road and a voice that guides you at the right time. If you’ve always dreamed of doing Route 66 for real, this audio guide is the most authentic and simple way to live it.

Entry ticket and self-guided audio tour of Skydeck and the city of Chicago are available in a separate app — the WeGoTrip app. You will receive an email from WeGoTrip with the link to download the app with the ticket and the digital guide. The digital guide includes maps, photos, scripts, and audio commentary. You will see Chicago from above and on foot with a Skydeck ticket and self-guided audio touring-app audio tour. Soak up history and panoramas of the place that Frank Sinatra called "My kind of town" and after your visit to the Skydeck, continue your journey on foot, uncovering the stories behind what you saw. Visit Millennium Park, cross the Chicago River and stroll along the Magnificent Mile

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and peaceful gardens, all while soaking in the city’s energy, ending at Queen’s Landing, where the city meets the lake, and the skyline stretches as far as you can see. You'll learn the history of the city, see the sites, learn about what you are seeing and be guided step by step by our walking tour app.

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore the birthplace of the skyscraper, visit landmarks like the Chicago Theatre, the Pablo Picasso at the Daley Plaza, and Millennium Park, and see how the city rose from the Great Fire to define modern design. Led by a friendly local guide who’s passionate about Chicago’s history and architecture, this tour brings the skyline to life one building, story, and photo stop at a time. Whether you’re an architecture enthusiast, a first-time visitor, or a curious local, you’ll walk away seeing Chicago in a whole new way.

Skip the crowds—this is a private tour for your group only! “Chicago’s Festive Lights: A Magical Christmas Journey” takes you through the heart of the Windy City during the most wonderful time of the year. Begin your tour at 875 North Michigan Avenue (formerly the John Hancock Center), adorned with holiday decorations and offering spectacular views of the city’s festive lights. Stroll down N State St, a vibrant street bustling with holiday shoppers and seasonal displays. Conclude your tour at Christkindlmarket Chicago, a traditional German holiday market filled with crafts, food, and the spirit of Christmas—an authentic and memorable way to experience the joy of a Chicago Christmas. Itineraries are subject to change based on availability.

Skip the crowds this is a private tour for your group only! How about an unforgettable time in Chicago with your beloved? If you're looking to have the most romantic time while visiting famous attractions of Chicago, then you can't miss this walking tour! Why is Chicago called "The Windy City"? Did you know that Chicagoans call The Cloud Gate "The Bean"? Do you know why? Together with the professional tour guide you will discover so many different facts about Chicago and you will hear the most romantic stories as you walk along the beautiful and historical streets of Chicago. Fill your hearts and memories with the most beautiful views and photos of The Windy City!

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist hub and its modern gentrification. Key Highlights: * Radical History: Learn about labor leader Lucy Parsons and the search for hidden bombs in the park. * Beer Baron Row: Hear tragic tales of murder and madness tied to grand Victorian mansions. * Quack Medicine: Discover how Theophilus Noel’s "Vita-Ore" empire funded iconic local architecture. * Mob Intrigue: Visit the former Russian Baths where mobsters met in steam rooms to avoid FBI wires. * Massacre Connections: See where the St. Valentine’s Day Massacre was planned and its getaway car destroyed.

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. Begin at Millennium Park where Anish Kapoor's Cloud Gate reflects the skyline that pioneered skyscraper design and continues to push architectural boundaries today. Wander along the Chicago Riverwalk where boat tours explain how the city reversed the river's flow and rebuilt in steel and stone after the Great Fire of 1871. Marvel at the ICAs world-class collection. Explore the Magnificent Mile's shopping and historic Water Tower, then discover the vibrant neighborhoods where Polish, Mexican, and African American communities have shaped Chicago's culture. Experience the blues at clubs where Muddy Waters and Buddy Guy defined a genre, then savor deep-dish pizza in the taverns that perfected this Chicago original.

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for the elite to a vibrant, diverse community shaped by migration, policy, and social change. Explore iconic landmarks like the Museum of Science and Industry while gaining insight into the impacts of racial segregation and urban renewal. This tour is designed for history buffs and urban studies enthusiasts, offering a nuanced perspective on the intersection of race and community development. - Walk through Hyde Park and learn about its historical significance - Visit key sites related to civil rights and urban policy - Understand the neighborhood's transformation and ongoing challenges - Perfect for history lovers and those curious about social dynamics

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Windy City. See iconic venues like the Chicago Theatre and Willis Tower, while learning fascinating stories about Al Capone and Prohibition. An enriching experience for architecture, history and gastronomy lovers, all in one day. - 7.2 km tour through points of interest in Chicago - Discover the historical and modern heritage of the city - Explore at your own pace with captivating audio stories - Ideal for travelers in a hurry or those on a quick visit to Chicago

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellence, resilience, and activism that transformed both the city and the nation. From Underground Railroad stations to civil rights battlegrounds, you’ll discover how Chicago became a beacon for those seeking freedom and opportunity. Starting at the site of Jean Baptiste Point DuSable’s mansion near the Chicago River, you’ll follow the footsteps of the city’s founder: a Black man who established Chicago’s first trading post in the 1770s. You’ll walk through the heart of the Loop, exploring sites where pioneering entrepreneurs like John Jones built businesses that became platforms for activism. The tour ends at Grant Park, where Barack Obama delivered his historic presidential acceptance speech in 2008 – a moment that represented the culmination of generations of struggle.

Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, and complete challenges for a unique experience blending sightseeing with gaming. Explore the Magnificent Mile and Cultural Mile with this unique adventure: Solve puzzles, explore the city, and find hidden gems at your own pace. Try a new type of experience with your smartphone, the perfect mix between a walking tour, sightseeing, and a scavenger hunt.

Explore the underground drinking culture of Chicago during the Prohibition era on this captivating app-guided walking tour. Uncover the secrets of hidden bars and speakeasies while learning about the city's notorious figures like Al Capone. This evening tour blends fascinating stories of gangsters and bootleggers with Chicago's vibrant cocktail and beer scene, making it an ideal experience for history lovers and cocktail enthusiasts alike. - Visit intriguing speakeasy-style venues and secret bars in Chicago's Loop - Discover the rich history of Prohibition and its impact on the city - Optional purchase of drinks and food at most stops, with recommendations provided - Perfect for history buffs and those seeking a unique night out in Chicago

Relive this city’s most remarkable historic events while visiting the towering buildings, fascinating sculptures, and beloved public spaces built by generations of Chicago laborers who brought to life the ingenious ideas of some of the world’s most influential designers.

Uncover the essence of Chicago's sports culture on this guided tour through the downtown area. Learn about the city’s iconic sports figures, explore fascinating stories, and discover the hidden sports landmarks that define the lives of Chicago fans. This tour offers a unique perspective on how sports are woven into the fabric of the city, providing insights that only a local guide can share. Whether you're a die-hard sports fan or just curious about the city's history, this tour is perfect for anyone looking to delve deeper into Chicago's athletic legacy. - App-Guided tour focusing on Chicago's rich sports history - Explore the downtown area and discover hidden sports icons - Learn about legendary figures and their impact on the city - Ideal for sports enthusiasts and those interested in local culture - Opportunities to purchase Chicago sports-related souvenirs

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.