Chicago’s 77 neighborhoods — 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 center, writers’ museum, river walk, design-centric 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 theaters, design shops and breweries. Late fall and winter are bargain times to appreciate them, when rates for everything from airfare to hotel rooms drop. But the best reasons to visit Chicago now largely defy climate.
1) 2:30 p.m. 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 Center. It’s the start of the center’s famous riverboat architectural tours ($47), now launching from across the street (through Nov. 19). 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 crowdsourced stories, bring the art of storytelling to life (admission $12).
2) 7 p.m. 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 characterizes Chicago’s vibrant restaurant scene. The chef Jimmy Papadopoulos uses global ingredients and cooking techniques to create richly flavored, multi-textured seasonal dishes including, recently, a salad with port-marinated pears ($14) and grilled lamb belly with eggplant, pickled grapes and chickpea crackers ($36). Menu splurges include the Instagram-famed oyster pie ($68), but guests needn’t 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.
3) 10:30 p.m. 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 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 Theater, where the Improvised Shakespeare Company specializes in long-form improv using the playwright’s language to craft two-act comedies based on a single audience title suggestion (tickets $20).
4) 10 a.m. Art History at Home and Abroad
You don’t need us to tell you to go to the Art Institute of Chicago (admission $20 to $25). But while you’re there, here are a few specifically Chicago-centric exhibitions you might otherwise overlook. Through Jan. 6, “Hairy Who? 1966-1969,” features the boldly graphic work of six countercultural South Side-based artists. Then make your way to the quirky Thorne Miniature Rooms, a subterranean collection of 68 dollhouse-scale architectural vignettes from a Gothic church and Tudor great room to a New Mexican dining room in the 1940s. All were designed by Narcissa Niblack Thorne, a Chicago artist and the wife of James Ward Thorne, heir to the Montgomery Ward retail fortune. From Nov. 17 to Jan. 8, several of the rooms are decorated in denominationally appropriate holiday style.
5) 12 p.m. 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 south to the Chicago River to stroll on the two-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 off-season, the walkway offers good perspectives on the surrounding landmark high-rises.
6) 2 p.m. Style Sales
After appreciating design in the city, take a souvenir home from a clutch of North Side shops that specialize 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 neighborhood, visit Brimfield for vintage plaid blankets and college pennants. Next door, Scout deals midcentury furnishings and funky finds as well as Impressionist Chicago cityscapes by the local artist Chuck Meyers.
7) 4 p.m. Brew Break
The explosive Chicago microbrew scene is largely neighborhood-based, from Argus Brewery in the South Side Pullman district and Moody Tongue Brewery in Pilsen to Temperance Beer Company in north suburban Evanston. Among the most popular, Half Acre Beer Co. recently opened a tap room, restaurant and beer garden just west of Andersonville. Claim a rustic wood table and a pint of its signature Daisy Cutter pale ale, Pony pilsner (each $6) or wet-hopped black ale Sticky Fat ($8) to relax in the family-friendly locale. Alcohol-free options include local Dark Matter Coffee ($2) and 164 Soda ($3). When hunger strikes, don’t miss the housemade bread ($6) and roast chicken ($18).
8) 7:30 p.m. Tiny Houses
Five major theaters in Chicago, including Steppenwolf and Goodman theaters, claim Tony Awards. But it’s the city’s small, often storefront-based theaters — over 200 of them exist — that form the backbone of the rich theater community. Go intimate at A Red Orchid Theater in Old Town where the actor Michael Shannon is a founder. The ensemble-focused Strawdog Theater in the North Center neighborhood is known for immersive staging of new works and rewritten classics such as “Great Expectations.” Steep Theater 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 post-curtain at the theater’s new adjacent bar.
9) 10:30 p.m. Toddlin’ Town
In a town where nightclubs and bars stay open an extra hour on Saturday nights, there’s a nightcap for every mood. The polished new Z Bar at the Peninsula Chicago hotel offers bird’s-eye views over Michigan Avenue’s Magnificent Mile downtown. In bohemian Wicker Park, the intimate Up Room atop the Robey hotel channels a midcentury lounge with Chicago accents, including drinks inspired by the Great Fire of 1871, such as Holy Cow milk punch ($15). In the Loop, enter through a neighboring diner to reach the neo-dive-bar Moneygun and huddle in a circular booth with a classic cocktail like a Pink Squirrel ($11.75). Nearby, play a game of foosball or bocce ball at the retro Game Room in the Chicago Athletic Association.
10) 10 a.m. Lakefront Tour
Eighteen 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 traffic-free 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).
11) 12 p.m. 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 (through Dec. 30) 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 farm-to-table pioneer with Lula Cafe in Logan Square, brings his savory skills downtown to the fittingly modern space. Indulge in a housemade doughnut ($4) frittata ($14) and crispy pork succotash ($16), then walk it off on the nearby Magnificent Mile stretch of Michigan Avenue.
The 1929-vintage Carbide and Carbon Building newly houses the 364-room St. Jane hotel in the Loop. Named for the pioneering social worker Jane Addams, the hotel plans to donate 1.1 percent of hotel revenue to a local charity. Guests will find local brands in the minibar and a destination all-day American brasserie, Free Rein, on the ground floor. Rooms from $269; stjanehotel.com.
Though occasional downtown apartments come up on Airbnb, most rentals tend to cluster in more residential neighborhoods. Those in the Old Town district tend to run from $64 to $130 and offer easy mass-transit access north or south via the Red or Brown Line trains. In the opposite direction and conveniently on the Red Line, look for good deals in Chinatown, where apartments start around $65. Airbnb.com.