36 Hours in Chicago (Published 2014) (2024)

Chicago is a city that changes noticeably with the seasons. It is endlessly beautiful in the warm months, when the sidewalks transform into cafes, the Lakefront Trail becomes a Divvy Bike highway and the beaches along Lake Michigan might be mistaken for Miami. As the temperatures fall, the city changes from a playground to a cultural promised land — a place of fine and varied food, inventive theater and one of the country’s great live music scenes. From the historic high-rises of the Gold Coast to regal Hyde Park, from Bronzeville to Boystown, from the Indian and Puerto Rican enclaves of Devon Avenue and Humboldt Park, respectively, to the bohemian barrios of Logan Square and Pilsen, Chicago demands hard choices. It rarely disappoints.

FRIDAY

3 p.m.
1. From Russia With Love

Russian Tea Time is the kind of classic, white-tablecloth restaurant that helps old cities age gracefully. There’s nothing new here, just wonderful Ukrainian-style borscht ($6), Russian herring ($13.50) and Moldavian, Uzbek and Azerbaijani specialties on a busy downtown street. The tea service ($29.95) includes over 30 teas and a spread of sweets and savories such as Pozharski croquettes and rugelach, while the vodka flights feature house-flavored black currant, horseradish and ginger spirits. Just across Michigan Avenue, get a taste of the Art Institute of Chicago’s dizzying scope by dropping into one of its catch-it-while-you-can exhibitions, like “Art and Appetite: American Painting, Culture and Cuisine,” which surveys “the historical art of eating” through Jan. 27.

5 p.m.
2. Into the Air

From the third floor of the Art Institute of Chicago’s Renzo Piano-designed Modern Wing, follow the Nichols Bridgeway, also designed by Mr. Piano, which crosses over Monroe Street to Millennium Park. Magical during the summer, the park’s Lurie Garden was designed to be visited in winter too, when colorful blooms are replaced by the captivating shapes of frozen seed heads and panicles. Then, take Millennium Park’s serpentine, Frank Gehry-designed pedestrian bridge to the edge of Maggie Daley Park, still under construction, to see the next stage in the evolution of Chicago’s front yard. For a vertigo-inducing vantage without the $18 ticket to the Willis (formerly Sears) Tower Skydeck, head north on the Magnificent Mile to the Hanco*ck Tower’s 96th-floor Signature Lounge. The décor is dated, the wait and service often grating, but the sunset view of the Chicago skyline rewards one’s patience and pairs well with a classic martini.

7 p.m.
3. Food as High Art

Chicago has an international reputation for avant-garde restaurants, like the molecular gastronomist Grant Achatz’s famed Alinea, which makes this a city where it’s worth considering a splurge on a once-in-a-lifetime meal. On the Near West Side, Grace is among the newest of its kind. Though only about a year old, it has already earned two Michelin stars for its eight-to-12-course $185 prix fixe menus (the vegetable-centric “Flora” and the carnivorous “Fauna”), which change nightly and make use of esoteric ingredients like mashua leaf, aged grits and kokum. Reservations required, often weeks in advance.

9 p.m.
4. Dance Party

For a beer (and, if you choose, a less extravagant meal) venture two blocks west of Grace to Au Cheval, one of the city’s myriad new-school diners, where comfort foods like matzo ball soup ($8) and fried, house-made bologna sandwiches ($10.95) are served with an excellent, wide-ranging beer list. Then, hop down to Maria’s Packaged Goods and Community Bar, in Bridgeport, a mysterious storefront bottle shop with a bar in back that hosts a monthly “Secret Disco” and a D.J. most nights. Or, if you eat early, make the trek to Lincoln Square’s Old Town School of Folk, which has undergone a $16 million expansion. On Friday nights, the Global Dance Party series offers a dance class followed by either a live band or D.J.’d world music.

SATURDAY

9 a.m.
5. Pop Goes Chicago

For breakfast, try an enormous biscuit or a slice ($5) of one of several seasonal pie offerings — think caramel apple, roasted pumpkin cream and chocolate — made daily from scratch at Bang Bang, in Logan Square, where the crust features real lard and seasonal fillings. Lighter fare may be had at one of the two locations — one in River North, the other in Lakeview — of the coffee roaster Bow Truss, which hosts a pop-up bakery, with a rotating cast of bakers selling pastries, doughnuts, cookies and tarts. Then, seek out temporary galleries by the Pop Up Art (popupartloop.com) project, which converts the Loop’s vacant storefronts into art spaces. For an overview of the city’s celebrated architecture during the winter, when the beloved architectural boat tours are on hiatus, visit the Landmark Chicago Gallery’s architectural photo series at the Chicago Cultural Center (free), also in the Loop.