Leigh’s Chicago City Guide
Whether you’re visiting for the first time or looking for new spots to explore, our Chicago stylist, Leigh, has curated a list of her favorite places to shop, eat, and stay, in the Windy City along with some must-see experiences to round out your trip!
SHOPPING
For a luxurious shopping experience, the Shops at 900 in the Gold Coast offer a variety of high-end, one-of-a-kind boutiques that can’t be found elsewhere. Whether you’re searching for unique gifts, clothing, or books, this shopping destination feels like an art gallery where everything is for sale. For vintage lovers, Lost Girl’s Vintage is a must-visit with its two city locations. This shop combines funky interiors with a mix of fashion, art, and home decor. Don’t miss the Randolph Street Market, an antique lover’s dream. With high-end vintage fashion, rare designer pieces, and one-of-a-kind antiques, this market is perfect for finding one-of-a-kind treasures. Downtown, 260 Sample Sale is the ultimate spot to score great deals on luxury brand fashion, beauty, and home items during their rotating weekly sales.
TO EAT
Chicago’s restaurant scene is as diverse as its neighborhoods. Gretel is a cozy yet stylish spot that serves elevated comfort food paired with craft cocktails, and their burger is one you won’t want to miss. Downstairs, the cocktail lounge adds a fun, intimate touch to your evening. For inventive drinks and Asian-inspired dishes, Chef’s Special Cocktail Bar is a hidden gem that seamlessly combines creativity with flavor. If authentic Italian is calling your name, Sapori Trattoria is a family-owned gem where risottos and fresh pasta are made with seasonal ingredients for a truly classic dining experience. For something lively, Duck Duck Goat offers a modern take on Chinese cuisine with colorful, creative dishes in a vibrant atmosphere. For a more laid-back meal, Luxbar is a stylish yet relaxed spot known for its delicious weekend brunch options in the heart of the city.
TO DO
Exploring Chicago means embracing both its natural beauty and cultural vibrancy. Lakefront Trail is a scenic route along Lake Michigan that offers stunning views of the city’s skyline and lakefront, providing a quieter, less crowded alternative to Millennium Park. It’s great for walking or cycling. A Chicago staple for stand-up comedy, Zanies offers an intimate setting to enjoy top comedians. It’s a fun, low-key night out. In the West Loop, the Fulton Market District is a trendy area with an industrial charm, packed with unique restaurants, galleries, and boutique shops. If you’re looking to explore Chicago’s art scene, the Bridgeport Art Center houses studios, galleries, and creative spaces, providing a peek into Chicago’s local art scene.
TO STAY
When it comes to accommodations, Chicago has no shortage of stylish places to stay. The Robey in Wicker Park is a standout, offering sleek, modern design and panoramic 180-degree views of the city skyline. For those who prefer a trendy yet laid-back vibe, The Hoxton in the West Loop features a modern industrial aesthetic, and its rooftop bar provides the perfect place to unwind with sweeping city views. Across from Millennium Park, the Chicago Athletic Association Hotel blends historic charm with modern amenities, featuring original wood paneling and ornate details that transport you back in time. And while not a hotel itself, The J. Parker rooftop bar at Hotel Lincoln offers unbeatable views of Lincoln Park and Lake Michigan, making a stay at the vintage-inspired Hotel Lincoln even more memorable.
Chicago is a city that truly has it all—luxury shopping, world-class dining, rich culture, and unbeatable skyline views. Leigh’s guide offers a taste of the city’s best, whether you’re a first-time visitor or a local looking to rediscover Chicago. Want to work with Leigh? Contact us below!