With its magnificent architecture, a collection of world-class hotels, a food scene recognized by Bon Appétit as the best in the country, and the famous Millennium Park in the center of downtown, Chicago merits much more than the nickname "Second City." Recognized as one of the most design-forward in the country, this Midwestern metropolis is a second city no more. On the heels of the city’s Chicago Architecture Biennial, Chicago’s design renaissance is reaching even higher levels, with new restaurants, hotels, museums, and office structures pushing the envelope on both architectural brilliance and interior design.
Visitors flock to the city year-round, even in the depths of Chicago’s notoriously difficult winters. However, residents have found creative ways to stay warm and cozy, both inside and out—such as outdoor bars offering thick wool blankets, roaring fire pits, and warm-your-bones cocktails. Even so, Chicagoans will tell you: Visit from late spring to mid-autumn to experience the best that the city has to offer.
Where to Stay
Impressive design is a hallmark of the Gwen, a Luxury Collection Hotel. The property features hand-carved limestone accents by Chicago-born sculptor Gwen Lux and Art Deco artwork and furniture in the main lobby—it's no surprise that the city’s top influencers can be found sipping cocktails at the lobby bar. Considered by many to be one of the most beautiful suites in the city, the Gwen’s Superior Suite offers minimal yet chic 1930s design and an expansive outdoor terrace with breathtaking views of the lake and the storied city skyline.
Opened at the end of the 19th century, the Chicago Athletic Association is a testament to the warm spirit typical of the city. Located in downtown Chicago, mere footsteps away from the popular Millennium Park (more on that later), this hotel exudes elegance.
Away from downtown, located in the city’s River North neighborhood, is another hotel to check out, if purely for the design. The Claridge Hotel was designed in 1923 by native Chicago architect Walter Ahlschlager, and the recently renovated lobby pays homage to the '20s and '30s with gilt accents, a silk-wrapped custom chandelier, and gallery walls featuring black-and-white photos of the hotel when it was a residence in the '40s and '50s. "We wanted the lobby to be an extension of the guest room," says project designer Ali Bacon of Chicago-based firm The Gettys Group. “It felt natural for this communal space to be the ‘living room’ of the hotel, and by extension, the entire Gold Coast neighborhood."
Situated in the stark black Ludwig Mies van der Rohe AMA Plaza across from the Trump building, The Langham Chicago is discreet, with few signs indicating that the hotel occupies 13 floors of the building. However, as soon as you get off the elevator, you’re rewarded with an awe-inspiring art collection, hand-blown glass chandeliers, and floor-to-ceiling windows that let in plenty of light. The rooms feature more of the hotel’s famed Bauhaus-influenced design.
For a stay that feels more like home, book a few nights in the West Loop’s ultra-trendy Publishing House Bed and Breakfast. Housed in a 110-year-old former publishing house, this loft-turned-bed-and-breakfast blends minimalist decor with contemporary design: claw-foot tubs and local artwork in the guest rooms, soft and worn leather chairs and a statement cement-and-slate fireplace in the middle of the lobby. Elements of the building’s history—first as a publishing house, then as a casket factory and holography museum—are seen throughout, such as industrially outfitted tall ceilings and floor-to-ceiling square-tiled windows.
Where to Eat and Drink
Go back in time for breakfast at Wormhole Coffee, a quirky and eccentric café in Wicker Park accented with a DeLorean (from Back to the Future), novelty movie posters, mismatched mugs, and ample family seating. You’ll find some of the neighborhood’s hippest people here, sipping java while furiously typing on their laptops. For something more elevated, visit Café Robey, a bright and airy restaurant tucked inside The Robey hotel. Here, you can enjoy avocado toast, fresh-pressed juices, and an array of delicious bites in their retro booths. Proxi, a West Loop favorite for brunch, also plays to the retro diner vibe, with orange round-booth seating, big patina mirrors, large-scale houseplants, and a gold-plated bar.
In keeping with the trend of live accents and cascading houseplants, Aba—located in hipster haven Fulton Market—is an Instagrammer's dream. A large portico draped in English ivy, flourishing plants at every corner, and a garden-themed patio with topiary bushes and lush planter boxes, Aba was inspired by a summer in the Mediterranean, according to senior designer Avril Zayas. “I have always loved greenery in indoor spaces," Zayas explains. "It creates a natural element that feels relatable and comfortable to guests."Boka incorporates the greenery trend, with a living moss wall in their private dining room, and a patio decorated with bulb lights and a small yet verdant garden.
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Open a discreet large black door and you enter one of Chicago’s most famous and beautifully designed steakhouses, GT Prime. Unlike other steakhouses in the city, GT’s design theme is fairy tales, according to lead designer Karen Herold of Studio K. The host stand is flanked by two large animal heads, the stools in the bar are wrapped in faux fur, and rich, velvety royal purple elements can be seen throughout. The waiter’s station in the middle of the room is the focal point, with two giant log cabin–esque pillars and a grand chandelier.
Though Chicago is no stranger to cocktail bars, the drinking scene has seen the biggest growth in terms of design. Z Bar, the popular rooftop spot in the swanky Peninsula Hotel, has a more contemporary feel than the rest of the property, but it still focuses on Chicago. “I sought inspiration from the city of Chicago…the dramatic bean-shaped skylight set into the 13-foot-high ceiling above the bar casts light onto hand-painted mural wall coverings that feature Chicago’s signature bascule bridges. The front lounge pays subtle homage to city architecture through a vocabulary of lines and materials, including hexagonal-patterned, mixed-marble floors,” says lead designer Yabu Pushelberg.
With a nod to Prohibition-era Chicago, The Violet Hour is one of the city’s most beautiful speakeasies. Hidden behind a street-art-decorated brick door, the lush tapestries, teardrop chandelier, and velvet couches and chairs sit behind elegant curtains. (The cocktails are just as design-forward.) Located in the midcentury-modern Conrad Hotel, Baptiste and Bottle looks and feels like a high-end whiskey bar. Custom millwork pieces showcase the restaurant’s extensive liquor collection, and the artwork includes a large abstract collage of whiskey ingredients and stills, as well as a series of illustrations detailing the whiskey-making process.
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What to Do
In a city revered for its architecture, any design lover would be remiss not to take a Chicago Architecture Tour. There are many ways to do this, but most people opt for one of the boats. You’ll weave along the recently renovated and rebuilt Riverwalk, spotting the city’s famous skyscrapers—like theMART and the wave-inspired Jeanne Gang–designed Aqua skyscraper—from the water. For an aerial view of the city’s architecture and landscape, take a helicopter tour. The LondonHouse hotel’s rooftop bar, located on Upper Wacker’s riverfront, also provides inspiring views of Chicago’s downtown.
Millennium Park is a large public open space that is home to a collection of sculptures, including Anish Kapoor’s Cloud Gate and Frank Gehry’s Pritzker Pavilion. Located just a few blocks away is the famous Art Institute of Chicago. Designed in 1893, the Beaux Arts building is a college, museum, and conference center; at night, the striking building offers beautiful views of the city skyline. Although the outside seems rather unassuming, the interiors are what make the Chicago Cultural Center a must-see. Standouts here are a spectacular Tiffany Dome (believed to be the largest in the world) and the intricate Healy-Millet Dome, both of which are free to see.
Away from the hustle of downtown, the Garfield Park Conservatory is a favorite of locals, especially in the cold winter months. This 4.5-acre conservatory is home to thousands of plants, trees, and flowers, with the focal point the palm-fringed prismed dome you see as soon as you enter.
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Two other can’t-miss neighborhoods for street art, restaurants, and design are Wicker Park and Andersonville. The go-to spot for design inspiration, Wicker Park is home to the city’s hippest shops, the architectural marvel The Robey hotel, and the famed Chicago mural below the Blue Line tracks. Here, you can hop on the 606 — the nearly three-mile-long, multiuse recreational trail that was once an abandoned railway. Andersonville’s Swedish roots are visible throughout the Northeast neighborhood—from the lush landscaping to the trendy Andersonville Galleria. The exposed-brick loft building features dozens of local vendors, selling everything from custom-made artwork to hand-stitched clothing and photography.
