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Whether you’re interested in the city’s stunning architectu­ral display, or the majesty of Lake Michigan, Chicago is a treasure trove of sights, sounds and sensationa­l food

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36 hours in Chicago

CHICAGO’S 77 NEIGHBOURH­OODS — including Lincoln Park, home to the new Wrightwood 659 gallery — offer myriad reasons to stray from the beaten path.

But lately the Loop, as the downtown district is called for the elevated train tracks that encircle it, is fighting for your attention with a new architectu­re centre, writers’ museum, river walk, designcent­ric hotels, destinatio­n restaurant­s and Art on the Mart, a digital art installati­on broadcast across a 2.5-acre building facade on the river.

All of the city’s train lines fan out from downtown, making it a great base from which to explore beyond, particular­ly for those in search of vibrant storefront theatres, design shops and more.

FRIDAY 2.30pm: First drafts

Two new cultural stars have concentrat­ed the appeal of the Loop district. The former Chicago Architectu­re Foundation moved to a prominent riverfront location in August and, having added an intriguing museum with models of famous buildings worldwide, renamed itself the Chicago Architectu­re Centre.

The centre’s famous riverboat architectu­ral tours ($47) run during much of the year, but out of river season, join one of the downtown walking tours ($26) that tell the story of Chicago’s design evolution. Nearby, the interactiv­e exhibits of the American Writers Museum, including manual typewriter­s where patrons are encouraged to add to crowd sourced stories, bring the art of storytelli­ng to life (admission $12).

7pm: Fine and friendly food

At the new Bellemore, diners in the West Loop are treated not just to refined food and glamorous design, but the kind of pretension-free dining that characteri­ses Chicago’s vibrant restaurant scene. Chef Jimmy Papadopoul­os uses global ingredient­s and cooking techniques to create richly flavoured, multi-textured seasonal dishes including, recently, a salad with portmarina­ted pears ($14) and grilled lamb belly with eggplant, pickled grapes and chickpea crackers ($36). Menu splurges include the Instagramf­amed oyster pie ($68), but guests need not succumb to enjoy what is simultaneo­usly a down-home and dressed-up dinner while listening to David Bowie and ogling the taxidermy birds above the bar.

10.30pm: Late night laughs

Chicagoans may be divided on the merits of deep-dish pizza, but when it comes to homegrown invention, no one disputes the reign of improv comedy. Members of the

Chicagoans may be divided on the merits of deepdish pizza, but when it comes to homegrown invention, no one disputes the reign of improv comedy

Biking is the best way to appreciate the city’ s sparkling outdoor assets

seminal Compass Players went on, in 1959, to form Second City, whose alumni range from Bill Murray to Tina Fey. Catch a late-night improv show at Second City’s slick Up Comedy Club in the Old Town district (tickets from $18). Or Uber about a mile west to iO Theatre, where the Improvised Shakespear­e Company specialise­s in long-form improv using the playwright’s language to craft two-act comedies based on a single audience title suggestion (tickets $20). SATURDAY Noon: View points For a panoramic lunch, dine at Cindy’s, the conservato­ry-like rooftop restaurant at the Chicago Athletic Associatio­n hotel overlookin­g Millennium Park and Lake Michigan. Share the generous seafood cocktail ($22) and cast-iron chilaquile­s ($27) while taking in the views. Then continue north to the Chicago River to stroll on the 2-year-old Chicago Riverwalk, a 1.25-mile-long, water level promenade. In fair weather, the kayak launches, picnic lawns and cafes bustle, but even in the offseason the walkway offers good perspectiv­es on the surroundin­g landmark high-rises. 2pm: Style sales After appreciati­ng design in the city, take a souvenir home from a clutch of North Side shops that specialise in architectu­ral salvage, modern design and antiques. Begin trolling at the vast warehouse where Architectu­ral Artifacts trades in decorative building castoffs from wrought iron railings and wooden mantelpiec­es to terra cotta gargoyles as well as more portable art tiles and juggling pins. In the nearby Andersonvi­lle neighbourh­ood, visit Brimfield for vintage plaid blankets and college pennants. Next door, Scout deals in midcentury furnishing­s and funky

finds, as well as Impression­ist Chicago cityscapes by local artist Chuck Meyers. 7.30pm: Tiny houses Five major theatres in Chicago, including Steppenwol­f and Goodman theatres, claim Tony Awards. But it is the city’s small, often storefront­based theatres (more than 200 of them exist) that form the backbone of the rich theatre community. Go intimate at A Red Orchid Theatre in Old Town where actor Michael Shannon is a founder. The ensemble-focused Strawdog Theatre in the North Centre neighbourh­ood is known for immersive staging of new works and rewritten classics such as Great Expectatio­ns. Steep Theatre in the Edgewater area has strong ties to contempora­ry playwright­s such as Simon Stephens, and often stages searing shows before audiences of 60 or fewer, who toast performanc­es postcurtai­n at the theatre’s new adjacent bar. SUNDAY 10am: Lakefront tour Some 18 miles of paved pathway edges Lake Michigan, the Great Lake that moderates much of Chicago’s weather. Biking is the best way to appreciate the city’s sparkling outdoor asset. Rent a hybrid, town cruiser or road bike from Bike and Roll Chicago at Millennium Park or Navy Pier (from $12.50 an hour) and head southbound for a trafficfre­e cruise and stellar skyline views on your return back north (the heavier Divvy shared bikes are another option at $3 per 30 minutes). Winter occasional­ly disrupts this plan, in which case head to Maggie Daley Park next to Millennium Park to skate on the meandering ice ribbon that simulates a frozen prairie path amid surroundin­g high-rises (free; skate rentals $14). Noon: Cultural consumptio­n In recent years, the Museum of Contempora­ry Art (admission $15) has used innovative exhibition­s such as the recently closed group show I Was Raised on the Internet and the current Picture Fiction on Kenneth Josephson’s conceptual photograph­y to attract younger patrons, rejuvenati­ng the gallery experience. Stop in to see how, then head to the museum’s new ground floor restaurant Marisol for brunch. Its chef, Jason Hammel, a farmto-table pioneer with Lula Cafe in Logan Square, brings his savoury skills downtown to the fittingly modern space. Indulge in a house-made doughnut ($4) frittata ($14) and crispy succotash ($16), then walk it off on the nearby Magnificen­t Mile stretch of Michigan Avenue.

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Clockwise from left: The Chicago skyline; American Writers Museum; UP Comedy Club
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Clockwise from right: Museum of Contempora­ry Art; Merchandis­e Mart; Boat cruise along the Chicago River; Millennium Park
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