Live in the lap of luxury on your weekend escape in downtown Chicago. Bespoke tours, world-renowned restaurants, and couture shopping sprees are just the beginning. Get ready to be wowed by the city’s upscale experiences.
Day 1: The Magnificent Mile and city adventures
Morning
Start your day with an indulgent breakfast on the Parisian-styled patio or in the wood-paneled dining room at RL Restaurant, one of only four Ralph Lauren restaurants in the world. Then start shop hopping at upscale stores and designer boutiques — including Chanel, Prada, Cartier, and Dolce & Gabbana along The Magnificent Mile, Oak Street, and Rush Street.
Afternoon
Lunch on adventurous small plates and house-cured meats at The Purple Pig on Michigan Avenue before taking a luxury tour with Bespoke Experiences. Whether you’re looking for skyscrapers or underground, snowy winters or sunny summers, Bespoke Experiences will create the perfect itinerary for you.
Evening
Take a VIP Centennial Wheel ride at Navy Pier in a glass-bottomed, plush-seated, climate-controlled gondola. Then book a chauffeur with Windy City Limousine to whisk you to your exciting dinner destination in Lincoln Park. Set aside about three hours to dine at Alinea, where each course borders on performance art (dessert might be an apple helium balloon — need we say more?). Alinea has been voted one of the best restaurants in the world and is one of only 13 restaurants in the U.S. to earn the coveted Michelin 3-Star rating, so you know you’re in for a one-of-a-kind experience (and make sure you book well in advance). Then top off your lavish evening with a nightcap at The Aviary in Fulton Market, or head to The Office, an intimate speakeasy directly below The Aviary, serving classically inspired cocktails and vintage spirits.
Day 2: Fine arts and fine steaks
Morning
Take a private tour of the city’s art museums and galleries with Noble Art Tours, for an insider’s view of the Chicago art scene. Then explore Michigan Avenue’s art galleries to find masterworks by the likes of David Hockney, Jean Dubuffet, and Roy Lichtenstein to add to your private collection.
Afternoon
This is your time to relax. The Langham, Chicago’sChuan Spa is an oasis of tranquility in the heart of the city. Indulge in the Chuan Ritual Bath with aromatherapy, a salt stone sauna, and steam room. Or refresh both body and mind at The Peninsula Spa, with treatments inspired by Ayurvedic and Asian philosophies.
Evening
Now that you’ve found perfect zen, immerse yourself in Chicago’s inspiring performing arts at The Harris Theater for Music and Dance, part of the Millennium Park Campus or the Lyric Opera of Chicago, which overlooks the Chicago River. Afterwards, pamper yourself with a late dinner in the sumptuous, sunken dining room at RPM Steak. Located in Chicago’s River North neighborhood, the restaurant is a modern take on the traditional steakhouse, with a contemporary, chef-driven menu, an award-winning wine list, and a curated craft cocktail list you’ll find hard to resist. Or, for a true taste of the Midwest, reserve a table at Gibsons Bar & Steakhouse, where you can dine on succulent Gibsons Prime Angus Beef. Gibsons is the first restaurant group in the country to have its own USDA Certified Angus Beef Program.
