36 Hours in Chicago

Skip downtown for now and head to the Northwest Side to stroll the Bloomingdale Trail — known as the 606, a nod to the first three numbers shared by most Chicago ZIP codes. An elevated 2.7-mile-long park that evolved from an abandoned rail line, the 606 connects several neighborhoods with a trail lined by murals and native plants. (An easy access point is from the Damen stop on the C.T.A. Blue Line.) Follow your walk with a stop in Wicker Park, a neighborhood that has, in a generation, transformed from grungy art-and-rock enclave to a more grown-up (and moneyed) hub for restaurants and nightlife. Le Midi, a wine bar heavy on Mediterranean influences, opened in 2022 and became an immediate local favorite. Wine starts pouring at noon, accompanied by small bites that include vermouth-marinated-mushroom crostini ($8) and pork-and-pistachio pâté ($8).

Once a hub of meat processing back when the poet Carl Sandburg called Chicago “hog butcher for the world,” the West Loop is now one of the city’s fastest-growing neighborhoods — McDonald’s relocated its corporate headquarters there in 2018, and high-end condo towers keep popping up. Restaurants, like the Danish-influenced Elske and the line-out-the-door burger joint Au Cheval, are the true draw for visitors. If you can score a table, dine at the easygoing Rose Mary, which borrows from the cuisines of Croatia and Italy to produce heirloom tomato salad ($21), grilled clams ($19), tuna crudo ($22) and cevapi, a sausage dish ($20). Chicago is not a celebrity-spotting town, but this might be the place to bump into them: Even Jill Biden, the first lady, stopped in for dinner this summer.

Start your day by admiring the University of Chicago, a campus with architecture spanning Gothic to Modern, in the Hyde Park neighborhood. Rise early with the bookish Hyde Parkers at Roux, a Southern-style diner that opened in 2021 (don’t skip the pastries — when I stopped by at 7 a.m. recently, the classic powdered-sugar beignets were still warm). Follow with a guided tour of the Robie House (from $20), a Frank Lloyd Wright creation nearby that was inspired by the clean, horizontal lines of the Illinois prairie and underwent an $11 million renovation, unveiled in 2019. Wander to Jackson Park, to the east (and peek at construction beginning on the Obama Presidential Center, a project that could bring a development boom to the neighboring Woodlawn community). Or visit the DuSable, a museum of Black history in Washington Park nearby, a stroll west of the Robie House (opens at 11 a.m.; $14.50 admission for nonresidents, free for some visitors).

Many Chicago tourists make a beeline for the Loop, shorthand for the downtown district, to take a selfie in front of “Cloud Gate,” the shiny metallic sculpture that everyone calls the Bean. They will be disappointed for a little while: access to the Bean is limited until next spring, while its surrounding plaza undergoes much-needed renovations. But other beloved city institutions nearby are showing new life. Only blocks away, the Art Institute of Chicago is exhibiting the work of Remedios Varo, a Spanish-born Surrealist painter, until Nov. 27 ($32 general admission for out-of-state residents). Children can romp around at Maggie Daley Park, a true urban playground, or look at the Field Museum’s newest star, Sobek, a 46-foot-long Spinosaurus that was unveiled in June, now on display in the museum’s main hall ($30 basic admission for out-of-state visitors).

Designed by Studio Gang, the architecture practice led by Jeanne Gang, the St. Regis Chicago is a curvy stunner of a skyscraper that opened in May. It is the most eye-catching addition to the skyline in years, especially when cruising up DuSable Lake Shore Drive, and inside is a lush hotel and restaurant that feel practically un-Midwestern in their luxuriousness. The showstopper is Miru, where diners can choose from Japanese dishes like hamachi and lemon sushi ($22) and miso black cod ($44). The smoky house Bloody Mary is called the 1871, one of many references to the Great Chicago Fire you may notice during your visit. Ask for a table on the terrace for spectacular views of Lake Michigan, the Chicago River and the Ferris wheel at Navy Pier during golden hour.

No one needs to tell Chicagoans that the city has some of the best Mexican food anywhere (Chicago has more Mexican-born immigrants than any American metro area but Los Angeles). Find a delicious example with brunch at Kie-Gol-Lanee, a no-frills Oaxacan spot in Uptown, on the North Side (try the huevos a la Oaxaqueña, $13). From there, meander north through the historically Swedish neighborhood of Andersonville, now known for its stretch of bookstores and home-goods shops. Women & Children First, a bookstore, has anchored a busy corner of the neighborhood since 1990 (block lettering on its windows proclaim “Open today, open forever”). Newer to the area are Paper & Pencil, a tiny stationery shop; Rare Form, which specializes in art prints and antiques; and the Understudy, a gorgeously designed theater-themed bookstore and coffee shop that opened last year.