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 theatre 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
3pm
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 specialities on a busy downtown street. The tea service ($29.95) includes over 30 teas and a spread of sweets and savouries such as Pozharski croquettes and rugelach, while the vodka flights feature house-flavoured 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 January 27th.
5pm
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 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 colourful 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 .
7pm
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.
9pm
4 Dance Party
For a beer (and 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 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 DJ 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.
Saturday
9am
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 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 architecture during the winter, when the architectural boat tours are on hiatus, visit the Landmark Chicago Gallery's architectural photo series at the Chicago Cultural Center (free), in the Loop.
1pm
6 Get Saucy
In the Edgewater neighbourhood, Sauce and Bread Kitchen is worth the trip. This collaboration between Crumb bakery and Co-op Hot Sauce has a B.Y.O. (vodka) Bloody Mary bar ($12.99 for house-made mix, pickles and beef sticks for four) and wonderful sandwiches (from $5.99) like grilled eggplant with a pimento spread. Half of Co-op Hot Sauce's profits support a local arts nonprofit. Stay on the North Side for the Paper Machete, a "live magazine" hosted by the writer Christopher Piatt. The free event, held at the historic Green Mill jazz club at 3pm each Saturday, invites comedians, journalists and performers to speak on everything from pop culture to current events.
5.30pm
7 Beer Hour
The great Revolution Brewing was recently immortalised by the local director Joe Swanberg with his movie about the craft beer scene, Drinking Buddies. Sip a beer named for the likes of Eugene V Debs or Gerry Adams, president of Sinn Féin, then join the free 6pm tour at the Avondale Brewery. Another option is the Map Room, the youth hostel of the pub world. Its shelves are stocked with vintage National Geographics, and its beer list spans the globe. With over 50 taps and nearly 300 beers, Hopleaf is an Uptown institution that doubled in size last year, with plenty of space for serving moules frites ($13).
7pm
8 Chicago Seoul
Ruxbin in Noble Square is an unpretentious neighbourhood B.Y.O.B. restaurant serving surprisingly elegant dishes. With just 32 seats and a steampunk aesthetic, Ruxbin belongs to Edward Kim, a Chicago-born, Cordon Bleu-trained Korean-American chef who worked under Thomas Keller at Per Se. Kim mixes Asian flavours with Midwestern ingredients in dishes like a delicious seafood bourride with white beans, fennel, sake, sun-dried tomato, fines herbes and lemon aioli ($28) or a grilled octopus appetiser with chickpeas, pickled green onions, black soybean, grapes and ginger-scallion vin ($12).
9pm
9 Show Time
Opened in Roscoe Village last spring by the drummer, composer and Pitchfork Music Festival producer Mike Reed, Constellation is among the newest spots in a city overflowing with live music venues.
With influences as varied as Duke Ellington and John Cage, the space's mission is to promote "forward-thinking" jazz, improvisation and contemporary classical music. Less well-known than landmark theatres like the Steppenwolf or the Goodman, Lookingglass Theater Company is an imaginative company on the Near North Side, in the Water Tower Water Works building.
11.30pm
10 Late, Late Night
The city's after-hours bar scene is made possible by a Late Hour liquor license that allows select spots to stay open until 5am on Sunday mornings.
Hit one of the lesser-known late-night clubs like the Underground Wonder Bar, a colourful, and sometimes campy, River North destination for live blues, jazz, funk, rock, reggae, soul and more – plus comedy shows and open mikes.
The Wonder Bar is owned by Lonie Walker, the self-appointed "Queen empress of Transcendent Rockin Jazz" and the front woman of the house band, Lonie Walker and her Big Bad Ass Company Band, which plays Saturday nights from 10.30pm into the wee hours.
Sunday
10am
11 International Brunch
Vendors at the weekly new Maxwell Street Market, on the Near South Side, sell everything from imported produce to knickknacks, and food stalls like Rubi's serve tacos, spit-roasted al pastor and fresh salsas.
Another brunch option, farther south in Chinatown, is Yan Bang Cai, a Sichuan restaurant with powder blue booths that specialises in dishes from the Zibong region. Try the spicy poached fish ($14.95) in a broth of glistening red oil, or rabbit in spicy ginger sauce ($13.95).
1pm
12 Go analog
While other cities are seeing the disappearance of their independent music shops, Chicago's thrive.
Stop into Reckless Records in Wicker Park or Dusty Groove in Ukrainian Village, or head up to Logan Hardware, which has a Vintage Arcade Museum in back of its Logan Square shop, where customers play free. Milwaukee Avenue in Wicker Park is dotted with stylish boutiques, and Pilsen’s 18th Street has several vintage shops, including Modern Cooperative, with its gorgeous selection of midcentury modern furniture and home décor, and the works of local artists.
– New York Times Service
