Where to stay, what to do, where to eat. Experience the exhilarating whirl of Chicago’s grandeur: two days of exploration, delight, and luxury in the heart of the Windy City. Embark on your Chicago adventure from The LaSalle, a beacon of luxury and elegance ideally situated for exploring the city’s eclectic offerings. Within two days, a trove of experiences awaits you, accessible by foot or a swift Uber ride from the hotel.
Dive headfirst into the cultural hotpot that is Chicago, a metropolis known for its remarkable architecture, vibrant culinary scene, and world-class museums. As the third-largest city in the United States, Chicago offers a stunning blend of cosmopolitan sophistication and Midwestern hospitality. Whether you’re a seasoned traveler or visiting for the first time, the city’s rich history, diverse cultural offerings, and exciting attractions never cease to amaze.
Beyond the awe-inspiring views and mouthwatering delicacies, Chicago thrives in its theatrical scene and sporting events. Whether you choose to laugh the night away at Second City or cheer on Chicago’s beloved sports teams, the city brims with excitement and life.
Luxury Abounds at The LaSalle Hotel
Every exquisite journey begins with a haven of comfort and luxury, and for me, this destination was The LaSalle Hotel. Nestled in Chicago’s bustling financial district, the 21-story icon has redefined luxury, pairing sophisticated design with unparalleled service. The LaSalle’s rooms are a study in luxury, with meticulous design and finishes that effortlessly merge contemporary chic and Art Deco roots. The design duo, DiLeonardo International and Chipman Design Architecture, have expertly crafted an atmosphere of elevated casual elegance.
Of note is the hotel’s on-site dining experience, Grill on 21. As the name suggests, this 21st-floor establishment offers an exciting dining option for both hurried business lunches and lavish leisurely dinners. The service is meticulous, the food exquisitely crafted, encapsulating the refined essence of 21st-century dining.
Culinary Gems: The Dearborn and Ocean Prime Chicago
Dining in Chicago is an adventure of its own. A brisk walk from The LaSalle brought me to The Dearborn, an urban American tavern that perfectly balances sophisticated classics with ‘lick your plate’ delights. The brainchild of sisters Amy Lawless and Clodagh Lawless, The Dearborn is as much a tribute to Chicago’s storied past as it is an ode to its vibrant present. The laid-back ambiance, paired with an exciting menu (do try the pork belly appetizer!), offers an enriching culinary experience.
On the second evening, a shopping spree on Michigan Avenue found its perfect conclusion at Ocean Prime. Housed within the same building as the LondonHouse hotel, this restaurant offers a stunning setting complemented by an impressive menu. The ambiance is equally inviting, whether for casual socializing, business discussions, or simple indulgence. Ocean Prime’s seafood is a must-try, their impressive cocktail selection the perfect accompaniment to an evening of luxury.
Experiences to Cherish: Iconic Sights and Unforgettable Experiences
No trip to Chicago is complete without a rendezvous with the city’s iconic landmarks, all conveniently accessible from The LaSalle. Stroll along the mesmerizing landscapes of Millennium Park, and make a stop at Cloud Gate, affectionately known as ‘The Bean’ by locals. The Art Institute of Chicago, a trove of masterpieces, offers an immersive experience in art, history, and culture. Be sure to spare a moment of awe for the classics by Monet and Picasso, among others.
A meander along the Chicago River on the Chicago Architecture River Cruise reveals the city’s architectural splendor, while the Willis Tower (still the Sears Tower in my heart) offers a bird’s eye view of this urban masterpiece. Looking for a thrill? The Chicago Helicopter Experience gives you an unbeatable panoramic view of the city.
Day Two: Shopping, Entertainment, and Sports Galore
Shopping on Michigan Avenue, the “Magnificent Mile,” is an experience that is hard to match. From the world’s largest Starbucks to renowned brands like Nike and American Girl, the shopping scene in Chicago is as eclectic as it is extravagant.
Culture vultures should check out Chicago’s vibrant theatre scene. Whether you fancy the grandeur of Broadway hits or intimate storefront performances, Chicago’s theaters will captivate your imagination. And if sports are your thing, Chicago’s got you covered. The Bears, Cubs, White Sox, Bulls, and Blackhawks – they all call this city home.
Unwind from the day’s adventures in your tranquil sanctuary at The LaSalle, where luxury and comfort meet. As you drift to sleep, you’ll look forward to the city’s offerings for the next day. After all, at The LaSalle, you’re not just staying in the heart of Chicago – you’re living it.
Also read, the 5 Best Luxury Hotels in Chicago.
Christopher Parr, is the Editor and Chief Content Creator for Pursuitist, and a contributing writer to USA Today, Business Insider — and the on-air host of Travel Tuesday on Live at 4 CBS. He is an award-winning luxury marketing veteran, writer, a frequent speaker at luxury and interactive marketing conferences and a pioneer in web publishing. Named a "Top 10 Luxury Travel Blogger” by USA Today, Parr has also been selected as the official winner in Luxury Lifestyle Awards’ 2023 list of the “Top 50 Best Luxury Influencers and Bloggers in the World.”