Ultra Luxury Chicago Holidays
Art enthusiasts will find the Art Institute of Chicago particularly captivating, as it houses the largest Impressionist collection outside of Paris. Beyond this, the city boasts 56 other museums, 250 theatres, and 225 music venues, ensuring a rich cultural itinerary. The Museum of Contemporary Art and the Field Museum are also noteworthy stops for those seeking to delve deeper into art and science.
Chicago's architectural significance is undeniable, being home to the world's first skyscraper. For panoramic city views, the 360 Chicago Observation Deck in the John Hancock Building offers a thrilling experience, complete with a tilting ride for adrenaline seekers. The city's architecture often features custom limestone and marble elements, reflecting its historical ties to local quarries.
Families will find an abundance of activities, including the Lincoln Park Zoo, Shedd Aquarium, and Navy Pier, which is brimming with attractions suitable for all ages. For shopping enthusiasts, the Magnificent Mile - a 1.6-kilometre stretch of high-end boutiques and department stores - promises a luxurious retail experience.
A visit to Millennium Park to see the Cloud Gate sculpture, affectionately known as "The Bean," provides a perfect photo opportunity. This central landmark encapsulates the city's blend of artistic expression and community engagement.
Chicago's culinary scene is equally impressive, with a staggering 12,000 restaurants offering a plethora of dining options. From the famous deep-dish pizza to gourmet dining, the city's gastronomic offerings cater to every palate.
Whether exploring its architectural wonders, indulging in its diverse culinary scene, or relaxing in its numerous green spaces, visitors are assured an exceptional experience in the ‘The Windy City’.
Art enthusiasts will find the Art Institute of Chicago particularly captivating, as it houses the largest Impressionist collection outside of Paris. Beyond this, the city boasts 56 other museums, 250 theatres, and 225 music venues, ensuring a rich cultural itinerary. The Museum of Contemporary Art and the Field Museum are also noteworthy stops for those seeking to delve deeper into art and science.
Chicago's architectural significance is undeniable, being home to the world's first skyscraper. For panoramic city views, the 360 Chicago Observation Deck in the John Hancock Building offers a thrilling experience, complete with a tilting ride for adrenaline seekers. The city's architecture often features custom limestone and marble elements, reflecting its historical ties to local quarries.
Families will find an abundance of activities, including the Lincoln Park Zoo, Shedd Aquarium, and Navy Pier, which is brimming with attractions suitable for all ages. For shopping enthusiasts, the Magnificent Mile - a 1.6-kilometre stretch of high-end boutiques and department stores - promises a luxurious retail experience.
A visit to Millennium Park to see the Cloud Gate sculpture, affectionately known as "The Bean," provides a perfect photo opportunity. This central landmark encapsulates the city's blend of artistic expression and community engagement.
Chicago's culinary scene is equally impressive, with a staggering 12,000 restaurants offering a plethora of dining options. From the famous deep-dish pizza to gourmet dining, the city's gastronomic offerings cater to every palate.
Whether exploring its architectural wonders, indulging in its diverse culinary scene, or relaxing in its numerous green spaces, visitors are assured an exceptional experience in the ‘The Windy City’.
Art enthusiasts will find the Art Institute of Chicago particularly captivating, as it houses the largest Impressionist collection outside of Paris. Beyond this, the city boasts 56 other museums, 250 theatres, and 225 music venues, ensuring a rich cultural itinerary. The Museum of Contemporary Art and the Field Museum are also noteworthy stops for those seeking to delve deeper into art and science.
Chicago's architectural significance is undeniable, being home to the world's first skyscraper. For panoramic city views, the 360 Chicago Observation Deck in the John Hancock Building offers a thrilling experience, complete with a tilting ride for adrenaline seekers. The city's architecture often features custom limestone and marble elements, reflecting its historical ties to local quarries.
Families will find an abundance of activities, including the Lincoln Park Zoo, Shedd Aquarium, and Navy Pier, which is brimming with attractions suitable for all ages. For shopping enthusiasts, the Magnificent Mile - a 1.6-kilometre stretch of high-end boutiques and department stores - promises a luxurious retail experience.
A visit to Millennium Park to see the Cloud Gate sculpture, affectionately known as "The Bean," provides a perfect photo opportunity. This central landmark encapsulates the city's blend of artistic expression and community engagement.
Chicago's culinary scene is equally impressive, with a staggering 12,000 restaurants offering a plethora of dining options. From the famous deep-dish pizza to gourmet dining, the city's gastronomic offerings cater to every palate.
Whether exploring its architectural wonders, indulging in its diverse culinary scene, or relaxing in its numerous green spaces, visitors are assured an exceptional experience in the ‘The Windy City’.
Chicago’s skyline is a masterpiece, blending historic gems like the Tribune Tower with modern icons like the Willis Tower – and architectural river cruises provide a unique perspective on the city's world-renowned urban design.
Architectural Marvels
Chicago’s skyline is a masterpiece, blending historic gems like the Tribune Tower with modern icons like the Willis Tower – and architectural river cruises provide a unique perspective on the city's world-renowned urban design.
From indulgent deep-dish pizza to Michelin-starred dining, Chicago’s culinary scene is renowned. Sample Chicago-style hot dogs, prime steaks, and explore diverse global flavours in the city’s vibrant restaurant districts.
Culinary Excellence
From indulgent deep-dish pizza to Michelin-starred dining, Chicago’s culinary scene is renowned. Sample Chicago-style hot dogs, prime steaks, and explore diverse global flavours in the city’s vibrant restaurant districts.
Chicago’s lakefront is an urban oasis, offering sandy beaches, waterfront parks, and sailing excursions. Cycle along the Lakefront Trail or unwind at Navy Pier with stunning skyline views.
Lakefront Leisure
Chicago’s lakefront is an urban oasis, offering sandy beaches, waterfront parks, and sailing excursions. Cycle along the Lakefront Trail or unwind at Navy Pier with stunning skyline views.
next trip today
Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.
START A WHATSAPP CHATLuxury Chicago Hotels
Luxury Chicago Hotels
Four Seasons Hotel Chicago
Chicago, North America
The city and Lake Michigan views from Four Seasons Hotel Chicago are sure to impress. Also prepare to be awed by VIP-level service and luxury accommodation, with dining and leisure experiences designed to wow.
The city and Lake Michigan views from Four Seasons Hotel Chicago are sure to impress. Also prepare to be awed by VIP-level service and luxury accommodation, with dining and leisure experiences designed to wow.
The city and Lake Michigan views from Four Seasons Hotel Chicago are sure to impress. Also prepare to be awed by VIP-level service and luxury accommodation, with dining and leisure experiences designed to wow.
The Peninsula Chicago
Chicago, North America
Elegant, luxurious, expansive. Just some of the words that best describe The Peninsula Chicago located on the city’s Magnificent Mile. Savour first-class service, global dining experiences, superb leisure facilities, and an Asian-inspired spa.
Elegant, luxurious, expansive. Just some of the words that best describe The Peninsula Chicago located on the city’s Magnificent Mile. Savour first-class service, global dining experiences, superb leisure facilities, and an Asian-inspired spa.
Elegant, luxurious, expansive. Just some of the words that best describe The Peninsula Chicago located on the city’s Magnificent Mile. Savour first-class service, global dining experiences, superb leisure facilities, and an Asian-inspired spa.
The Langham, Chicago
Chicago, North America
The Langham, Chicago occupies a grand setting by the Chicago River, with a level of service designed to elevate every experience. Dining is always refined and indulgent, as is relaxation at the award-winning spa.
The Langham, Chicago occupies a grand setting by the Chicago River, with a level of service designed to elevate every experience. Dining is always refined and indulgent, as is relaxation at the award-winning spa.
The Langham, Chicago occupies a grand setting by the Chicago River, with a level of service designed to elevate every experience. Dining is always refined and indulgent, as is relaxation at the award-winning spa.
Waldorf Astoria Chicago
Chicago, North America
Waldorf Astoria Chicago presents the very best of Parisian style and warm American hospitality in the popular Gold Coast area. Every experience is elevated here - whether it’s drinks, dining, or the stunning spa services.
Waldorf Astoria Chicago presents the very best of Parisian style and warm American hospitality in the popular Gold Coast area. Every experience is elevated here - whether it’s drinks, dining, or the stunning spa services.
Waldorf Astoria Chicago presents the very best of Parisian style and warm American hospitality in the popular Gold Coast area. Every experience is elevated here - whether it’s drinks, dining, or the stunning spa services.
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Four Seasons Hotel Chicago
The city and Lake Michigan views from Four Seasons Hotel Chicago are sure to impress. Also prepare to be awed by VIP-level service and luxury accommodation, with dining and leisure experiences designed to wow.
The Langham, Chicago
The Langham, Chicago occupies a grand setting by the Chicago River, with a level of service designed to elevate every experience. Dining is always refined and indulgent, as is relaxation at the award-winning spa.
The Peninsula Chicago
Elegant, luxurious, expansive. Just some of the words that best describe The Peninsula Chicago located on the city’s Magnificent Mile. Savour first-class service, global dining experiences, superb leisure facilities, and an Asian-inspired spa.
Waldorf Astoria Chicago
Waldorf Astoria Chicago presents the very best of Parisian style and warm American hospitality in the popular Gold Coast area. Every experience is elevated here - whether it’s drinks, dining, or the stunning spa services.
Chicago in a nutshell
The city’s rich cultural heritage makes it a standout destination for ultra-luxury Chicago holidays. The Art Institute of Chicago, home to an extensive collection of masterpieces, is a must-visit. Meanwhile, theatre lovers can catch a Broadway-calibre production at the iconic Chicago Theatre or explore the city’s jazz and blues legacy at famed music venues. The Museum of Contemporary Art and the DuSable Museum of African American History add depth to the city’s artistic and historical narrative. For an immersive experience, private art tours and VIP theatre packages provide an exclusive glimpse into Chicago’s thriving creative scene. The Chicago Symphony Orchestra and the Lyric Opera also present world-class performances, appealing to classical music aficionados.
Tastes to try
Dining in Chicago is a fantastic experience, with top-tier restaurants offering everything from authentic deep-dish pizza to internationally inspired tasting menus. Seafood lovers can indulge in the freshest catches from Lake Michigan, while classic steakhouses serve premium cuts. The West Loop is a culinary hotspot, housing some of the best Michelin-starred restaurants the city has to offer. Whether dining with views of the Chicago River or in the lavish restaurants of luxury hotels in Chicago, foodies will find no shortage of exquisite options. Many top dining spots offer chef’s table experiences and curated wine pairings for an elevated gastronomic journey. The city’s food festivals, such as Chicago Gourmet, attract top chefs and food enthusiasts, showcasing the city’s ever-evolving culinary landscape.
After-dark destinations
As the sun sets, Chicago transforms into a city of dazzling nightlife. Rooftop bars offer breathtaking skyline views, while speakeasies and jazz lounges transport visitors to the Prohibition era. Live blues and jazz performances define the city’s after-dark appeal, creating an electric yet sophisticated atmosphere. For a unique experience, a moonlit architectural river cruise provides an exclusive way to admire Chicago’s illuminated landmarks. Late-night theatre shows and private whiskey tastings complete the city’s luxury nightlife offerings. Upscale lounges in luxury hotels Chicago cater to those seeking refined cocktails and intimate social settings, ensuring an unforgettable evening in the city. Exclusive rooftop lounges at high-end hotels provide a sophisticated retreat for those looking to enjoy handcrafted cocktails while gazing at the glittering skyline. From day until night, the Windy City is always full of surprises.
The city’s rich cultural heritage makes it a standout destination for ultra-luxury Chicago holidays. The Art Institute of Chicago, home to an extensive collection of masterpieces, is a must-visit. Meanwhile, theatre lovers can catch a Broadway-calibre production at the iconic Chicago Theatre or explore the city’s jazz and blues legacy at famed music venues. The Museum of Contemporary Art and the DuSable Museum of African American History add depth to the city’s artistic and historical narrative. For an immersive experience, private art tours and VIP theatre packages provide an exclusive glimpse into Chicago’s thriving creative scene. The Chicago Symphony Orchestra and the Lyric Opera also present world-class performances, appealing to classical music aficionados.
Tastes to try
Dining in Chicago is a fantastic experience, with top-tier restaurants offering everything from authentic deep-dish pizza to internationally inspired tasting menus. Seafood lovers can indulge in the freshest catches from Lake Michigan, while classic steakhouses serve premium cuts. The West Loop is a culinary hotspot, housing some of the best Michelin-starred restaurants the city has to offer. Whether dining with views of the Chicago River or in the lavish restaurants of luxury hotels in Chicago, foodies will find no shortage of exquisite options. Many top dining spots offer chef’s table experiences and curated wine pairings for an elevated gastronomic journey. The city’s food festivals, such as Chicago Gourmet, attract top chefs and food enthusiasts, showcasing the city’s ever-evolving culinary landscape.
After-dark destinations
As the sun sets, Chicago transforms into a city of dazzling nightlife. Rooftop bars offer breathtaking skyline views, while speakeasies and jazz lounges transport visitors to the Prohibition era. Live blues and jazz performances define the city’s after-dark appeal, creating an electric yet sophisticated atmosphere. For a unique experience, a moonlit architectural river cruise provides an exclusive way to admire Chicago’s illuminated landmarks. Late-night theatre shows and private whiskey tastings complete the city’s luxury nightlife offerings. Upscale lounges in luxury hotels Chicago cater to those seeking refined cocktails and intimate social settings, ensuring an unforgettable evening in the city. Exclusive rooftop lounges at high-end hotels provide a sophisticated retreat for those looking to enjoy handcrafted cocktails while gazing at the glittering skyline. From day until night, the Windy City is always full of surprises.
The city’s rich cultural heritage makes it a standout destination for ultra-luxury Chicago holidays. The Art Institute of Chicago, home to an extensive collection of masterpieces, is a must-visit. Meanwhile, theatre lovers can catch a Broadway-calibre production at the iconic Chicago Theatre or explore the city’s jazz and blues legacy at famed music venues. The Museum of Contemporary Art and the DuSable Museum of African American History add depth to the city’s artistic and historical narrative. For an immersive experience, private art tours and VIP theatre packages provide an exclusive glimpse into Chicago’s thriving creative scene. The Chicago Symphony Orchestra and the Lyric Opera also present world-class performances, appealing to classical music aficionados.
Tastes to try
Dining in Chicago is a fantastic experience, with top-tier restaurants offering everything from authentic deep-dish pizza to internationally inspired tasting menus. Seafood lovers can indulge in the freshest catches from Lake Michigan, while classic steakhouses serve premium cuts. The West Loop is a culinary hotspot, housing some of the best Michelin-starred restaurants the city has to offer. Whether dining with views of the Chicago River or in the lavish restaurants of luxury hotels in Chicago, foodies will find no shortage of exquisite options. Many top dining spots offer chef’s table experiences and curated wine pairings for an elevated gastronomic journey. The city’s food festivals, such as Chicago Gourmet, attract top chefs and food enthusiasts, showcasing the city’s ever-evolving culinary landscape.
After-dark destinations
As the sun sets, Chicago transforms into a city of dazzling nightlife. Rooftop bars offer breathtaking skyline views, while speakeasies and jazz lounges transport visitors to the Prohibition era. Live blues and jazz performances define the city’s after-dark appeal, creating an electric yet sophisticated atmosphere. For a unique experience, a moonlit architectural river cruise provides an exclusive way to admire Chicago’s illuminated landmarks. Late-night theatre shows and private whiskey tastings complete the city’s luxury nightlife offerings. Upscale lounges in luxury hotels Chicago cater to those seeking refined cocktails and intimate social settings, ensuring an unforgettable evening in the city. Exclusive rooftop lounges at high-end hotels provide a sophisticated retreat for those looking to enjoy handcrafted cocktails while gazing at the glittering skyline. From day until night, the Windy City is always full of surprises.
frequently asked questions
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next trip today
Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.