Chasing Chicago’s Trendiest Haunts

Discover dog-friendly hotels, smoke-swirling cocktails, and the world’s largest digital art display in this Illinois city.

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A little romance in Lincoln Park. Photo by: Hossein Fatemi/Panos Pictures

Coined in the 1830s, Chicago’s Latin motto, Urbs in Horto (“City in a Garden”), anticipated the green movement by more than a century. Since then Chicago has accelerated the pace of environmental innovation, building some 480 kilometres of bike trails, installing green roofs on buildings like City Hall, and creating the 24.5-acre Millennium Park atop a parking garage.

Public art and architecture have long been at the heart of Chicago’s cultural appeal, and the two now merge for Art on the Mart, a new digital projection across 2.5 acres of edifice. The city’s culinary trailblazers fuel cultural exploration and create their own enticing food-focused circuit.

“Chicago has surprising beauty, and the people are very comfortable with where they live,” says David Manilow, a Chicago native and the creator of restaurant review show “Check, Please!” “It’s a city where you’re allowed to be yourself.”

—Elaine Glusac


Global Goes Local

Chicago’s craft breweries look to the world for fermentation inspiration


Clockwise from top left: Spicy seafood and the private dining room at BiXi Beer; Cruz Blanca’s Palm Shade pale ale; Maplewood brews to go. Photos by: Madi Ellis (fish, dining room), Matt Mendini (cans), Marina Carsello (glass)

Corner taverns, common in Chicago, are known for the Old Style–brand beer signs that often hang out front. But these days many residents do their drinking in the craft beer taprooms that have bubbled up with such frequency that the Brewers Association recently found Chicago to be the nation’s centre of craft brewing—home to 167 breweries, more than any other U.S. city.

Forget those hyped and hoppy IPAs; brewmasters here have brought global varieties home. In Ravenswood, Dovetail Brewery specialises in rich Belgian and German styles. In Logan Square, Bixi Beer incorporates ingredients such as Sichuan peppercorns and green cardamom to align with its Asian-accented cuisine. Nearby, Maplewood Brewery & Distillery mixes it up by creating cocktails with both house brews and spirits. Cruz Blanca Brewery & Taqueria in the West Loop, part of chef Rick Bayless’s restaurant empire, channels a sunny Mexican spirit.

Neighbourhood pride has bolstered the craft breweries, most of which sit far from downtown’s financial centre. “The definition of ‘local’ used to be ‘from Chicago,’” says Manny Valdes, Bayless’s partner in Cruz Blanca. “Now it is, ‘What block are you on?’ The neighbourhood supports you.”


Windy City Stays


Four-legged guests soak in the scene at Chicago Athletic Association Hotel. Photo by: AJ Trela

Chicago Athletic Association Hotel

Built to impress travellers at the 1893 Columbian Exposition, the Venetian-inspired Chicago Athletic Association has stone fireplaces and leaded glass windows. Restored and reopened as a hotel in 2015, the Millennium Park-facing landmark attracts locals keen on its rooftop bar, Cindy’s; retro Game Room; and eight-seat speakeasy, Milk Room, specialising in vintage spirits.

St. Jane Chicago

In the art deco Carbide and Carbon Building, this 365-room newcomer honours its namesake—social activist Jane Addams—by donating a portion of the proceeds to charity. The building’s shape recalls that of a champagne bottle, so it’s fitting that restaurant Free Rein feeds the fizz with DJs, live music, and crowd-friendly seafood towers.

InterContinental Chicago Magnificent Mile

Location meets lore in this 1929 Michigan Avenue classic, originally the Medinah Athletic Club—as revealed in its marble-and-tile swimming pool. Michael Jordan’s Steakhouse, backed by the basketball great, frames views of columns and coffered ceilings. The hotel will even pack you a picnic for urban exploration.


Tradition and Trend

Dig into deep-dish, but also try innovative bites and sips

Foodie HQ

The city officially counts 77 communities, but many adventurous chefs have settled in Logan Square, opening a slew of casual, cutting-edge, and indie restaurants. The eclectic Lula Cafe helped pioneer the farm-to-table trend here 20 years ago and still serves area creatives morning, noon, and night. Newer destination dining rooms include Mi Tocaya Antojeria, where chef Diana Davila pays inventive homage to her Mexican heritage; Fat Rice, plating the fusion food of Macau; and the tiny-but-mighty Giant, with Midwest-meets-world fare.

Hall Pass

Food halls solve the “where should we eat” dilemma with something-for-everyone variety, a concept that has captivated Chicago diners. Revival Food Hall brings neighbourhood hotspots to a 1907 Daniel Burnham–designed building in the downtown Loop—and adds a bar and DJ for more buzz. Pop in pre-theatre for spicy chicken sandwiches from The Budlong, brisket from Smoque BBQ, and sweets from Hot Chocolate Bakery. On weekends, hit the Chicago French
, home to some 30 vendors.


Creative flair marks the menu at Mi Tocaya Antojeria. Photo by: Jude Goergen

Pizza 2.0

Chicago is, of course, synonymous with deep-dish pizza, a sturdy pie of two-inch caloric depths that can sustain citizens in the “city of the big shoulders.” But Chicagoans are passionate about pizza in all its forms. Union Full Board bakes square-pan Detroit- style pizza near Wrigley Field. In Ravenswood Spacca Napoli Pizzeria waves the Italian flag for authentic Neapolitan versions tended by a certified pizzaiuolo. For deep-dish gone truly decadent, join the line at Pequod’s Pizza, where cheese addictively caramelises the crust.

Cocktail Hour

Not to be outdone by inspired chefs, mixologists have raised the bar on invention. At The Aviary, in the West Loop, Grant Achatz applies a flight-of-fancy approach to drinks that send out wisps of smoke or deftly mimic flowers. (An open kitchen provides a peek behind the curtain.) The Violet Hour in Wicker Park won a James Beard Award for pours such as the mezcal-spiked Per My Last Email and rum-based Wherever I Wander. The new Bibliophile in Hyde Park gets literary with libations named after classic reads.


Shoreline to Skyline

Stroll waterside paths, obsess over architecture, and get your groove on

Exterior Design

When the Great Chicago Fire razed the city in 1871, rebuilding efforts focused on architectural innovation. The recently renamed Chicago Architecture Center, now housed in a Mies van der Rohe building, offers river cruises that tell the story of the city’s transformation into a megalopolis of cloud- tickling skyscrapers. You can also stroll the Chicago Riverwalk to ogle the landmarks. At night, catch the latest iteration of Art on the Mart, the projection that dances across the facade of the former Chicago Merchandise Mart.


Buddy Guy at his eponymous music club. Photo by: The Washington Post/Nels Akerlund

Outward Bound

Sun, rain, wind, or snow, residents embrace the weather and get outside. It helps to have the 30 kilometre Chicago Lakefront Trail that connects Lincoln Park with four others to encourage cycling, running, and rambling. There are also 27 beaches. If you’re a volleyball buff, hit the sand at popular North Avenue Beach. Outfitters provide guided kayaking excursions on the river and stand-up paddleboarding on the lake. Every Saturday morning birdwatchers meet on Jackson Park’s Wooded Island to add to their life lists.

Pursuing POTUS

Before he became president, Barack Obama lived here, working as a community organiser, Illinois senator, and University of Chicago law professor. Now, with the imminent construction of his presidential library, the Hyde Park neighbourhood is hot. Fans of 44 can spend the night at the new Sophy Hotel, themed to the university’s cultural and academic prowess; attend a storytelling session at the community-focused Silver Room boutique; and raise a glass to the Obama mural at the Cove Lounge.

Behind the Music

From Chance the Rapper to the Chicago Symphony Orchestra, music sets a big-time beat in this city. Explore the scene’s roots in jazz and blues with a stop at Uptown’s Green Mill Cocktail Lounge, a Prohibition-era speakeasy. Then join reverent audiences at the cabaret-style Winter’s Jazz Club near Navy Pier, or swing by the Jazz Showcase in the South Loop where Sunday matinees welcome all ages. Blues artists take the stage at Buddy Guy’s Legends, including the Grammy- winner himself during annual wintertime stints.





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