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 Hancock 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.