NEW YORK, NY.- First-time visitors to Chicago can find themselves awe-struck by the sheer scale of the place: the grand skyline, the vastness of Lake Michigan, and the miles of manicured parkland and beaches. Exploring all of Chicago, the nation’s third-largest city, is impossible in a single weekend, but that’s plenty of time to get a taste for what has made Chicago beloved by natives and tourists alike: easily navigable public transit, world-class museums, an eclectic mix of architectural styles, and an inventive restaurant scene that offers far more than an Italian beef and a shot of Malört. The city is shaking off its pandemic dust, setting records for hotel occupancy and getting ready for a big moment in the political spotlight next summer, when the Democratic National Convention comes to town.
ITINERARY
Friday
4 p.m. | Amble in the park
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 CTA 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).
6 p.m. | Dine in the West Loop
Once a hub of meat processing back when 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, including 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. Jill Biden, the first lady, stopped in for dinner this summer.
9 p.m. | Enter a cocktail cave
There are cocktail bars, and then there is the decadent After, known to Chicagoans as the creation of Curtis Duffy, a renowned chef. (Next door is Ever, the sleek fine-dining restaurant that played a role in the character Richie’s culinary education in Season 2 of “The Bear.”) Off a quiet street on the western edge of the West Loop, away from a busy strip of Randolph Street that attracts hordes on the weekends, After feels like a dark cave, hushed and intimate, with deep banquettes and a curved bar. Many of the drinks are a splurge, but beautifully prepared: Try the Herbal 75 ($23) or 24K Espresso Martini ($25), and nonalcoholic options are imaginative and delicious, too. A late-night weekend food menu from 10 p.m. to midnight offers Vietnamese duck wings ($20), French fries ($9) and crème brûlée with raspberries ($8).
Saturday
9 a.m. | Admire architecture
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; 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).
Noon | Romp around the Loop
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 unveiled in June, now on display in the museum’s main hall ($30 basic admission for out-of-state visitors).
1:30 p.m. | Stroll in elegance
On a quiet corner in the affluent Gold Coast neighborhood is the Lunchroom, a respite from crowds on the Magnificent Mile, Chicago’s main downtown shopping thoroughfare, and a refined place for an alfresco bite. Enjoy an Arnold Palmer ($5) and niçoise salad ($20.95) before shopping at the attached boutique, Space 519, which offers clothing, handbags, funky artwork and fragrances. Walk outside to marvel at the architectural gems in your midst: along Lake Shore Drive, the glassy twin Mies van der Rohe residential towers, a classic example of the architect’s modernist contributions to the city, or rare Gilded Age mansions built after the Great Chicago Fire of 1871. For a more structured guide to the neighborhood’s architecture, sign up for a 90-minute walking tour from the Chicago Architecture Center ($30 a person).
5 p.m. | Have Japanese bites
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 are a lush hotel and restaurant that feel practically un-Midwestern in their luxuriousness. The showstopper is Miru, where diners can choose from Japanese dishes such as 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.
7:30 p.m. | Find your seats
Regional theaters across the country are still suffering from smaller crowds and fewer paying subscribers, and the storied Steppenwolf in the Lincoln Park neighborhood is no exception, laying off 12% of its staff this year in the face of declining revenues. But Chicago’s love for theater runs deep, and Steppenwolf, which has been around since 1974, is still producing exceptional plays. (One of its shows, “Sanctuary City,” which runs through Nov. 18, is particularly well timed as Chicago struggles with an influx of migrants.) In 2021, the theater completed an expansion of its campus: The revamped Steppenwolf now includes the Ensemble Theater, a 400-seat, in-the-round space. You don’t have to look far for a nightcap after the show — two bars in the theater’s building are open late.
Sunday
10 a.m. | Savor Oaxacan Food
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 proclaims, “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.
1 p.m. | Trace the lakeshore
One thing that connects Chicagoans is Lake Michigan, provider of natural beauty, recreation and fresh drinking water. Get close to the lake and grab a Divvy bike for rental for a cruise down the 18-mile Lakefront Trail, taking in the splendor of the water, beaches and playgrounds that the preservationists of Chicago have long fought to protect. Follow your ride with lunch at Sfera, a tiny cafe blocks from the northern end of the bike trail that turns out delicious Sicilian street food. Don’t miss the perfectly balanced, fresh-squeezed limonata with housemade lemon syrup ($4) and arancini filled with porcini mushrooms and fontina ($12 for two).
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KEY STOPS
Robie House is a Frank Lloyd Wright masterwork, a restored example of his Prairie style architecture with public tours.
Sfera, a tiny cafe in Edgewater, is worth the trek for its limonata, arancini and proximity to Lake Michigan.
The 606, or the Bloomingdale Trail, is an elevated path for walking, running and biking that bridges neighborhoods.
Miru, a Japanese restaurant in the new St. Regis Chicago, has delicately prepared sushi and dazzling city views.
WHERE TO EAT
Le Midi is a wine bar and shop with a European feel, offering drinks and small plates.
Rose Mary is a West Loop hot spot with delicious pastas, seafood and Croatian wines.
After is a cocktail lounge with a richly decorated interior and an impressive menu of drinks and late-night bites.
Roux, a diner with Southern specialties, is one of the newest places to grab breakfast in Hyde Park.
The Lunchroom, around the corner from the bustle of Michigan Avenue in the Gold Coast neighborhood, is a quiet place for an elegant lunch.
Kie-Gol-Lanee makes Oaxacan food in a casual, no-frills environment in the Uptown neighborhood.
WHERE TO STAY
St. Regis Chicago is a new luxury entry in the city’s hotel scene, with a buzzy restaurant and serene interiors. Perks include an indoor swimming pool with a view of the Chicago River. Rooms start at $665.
Chicago Athletic Association is a classic choice on Michigan Avenue, across from Millennium Park. The hotel has seven restaurants, including Cindy’s, a local favorite. Rooms from $204.
CitizenM is centrally located downtown and a great home base for exploring. Its rooms, from $148, are on the compact side.
For short-term rentals, there are apartments aplenty in the River North or West Town neighborhoods, close to downtown.
This article originally appeared in
The New York Times.
