Photo by Maria Sbytova/Shutterstock
Photos by Jeff Marini
Head to Hyde Park for live music and great jerk chicken.
Chicago has some 77 neighborhoods, and numerous more sub-neighborhoods, each with its own charm. Explore a handful for a real insight into the third largest U.S. city.
Chicago, the third largest city in the United States, has been called a big city with a small-town feel, mostly for its numerous neighborhoods that seem to bring things a bit closer together. Since the city’s inception, immigrants have set up enclaves—Swedes in Andersonville, Poles in West Town and then up Milwaukee Avenue, Czechs and then Mexicans in Pilsen, Puerto Ricans in Humboldt Park, Ukrainians in, well, Ukrainian Village, and on and on—and created a multicultural patchwork that continues to influence life in the Windy City.
The 77 official neighborhoods further slice into sub-neighborhoods like Wrigleyville within Lakeview, Andersonville within Edgewater, Chinatown within Armour Square, and Ukrainian Village within West Town. It’s here where the real Chicago thrives.
Many visitors to Chicago tend to visit the more tourist-driven areas like Millennium Park, the Gold Coast, and River North. But to know Chicago is to get into the neighborhoods and explore the city’s rich, diverse history.
Here we highlight some of the best Chicago neighborhoods to help you make the most of your visit.
While few of the Swedish touches still exist—the Swedish American Museum, Svea restaurant, and Lost Larson for Swedish-inspired pastries (pro tip: get the cardamom bun) for example—the neighborhood celebrates its Nordic influence each June with the Midsommarfest street fair.
Today, Andersonville is arguably one of Chicago’s most vibrant neighborhoods with a mix of families and the LGBTQ calling it home, many in the historic Lakewood Balmoral District. The area has an array of eclectic shops like the Wooden Spoon for all things cookery, Foursided when you need unique gifts, antiques and beautiful furniture at Scout and Roost, men’s clothing and lifestyle at Cowboys and Astronauts, and Women & Children First bookstore, focusing on feminist, LGBTQ, and children’s books.
Dining and drink options seem endless, but don’t miss classic Italian fare at Anteprima, coffee at the mod-designed Coffee Studio, big-as-your-head martinis at Marty’s, one of Chicago’s best craft beer selections at Hopleaf, a little bit of everything at Little Bad Wolf, and fried chicken and negroni slushies at Parson’s.
The Guesthouse Hotel
Book now: from $199/night, expedia.com
Stay local at the Guesthouse Hotel, a great option with one- to three-bedroom suites with kitchens, living rooms, and balconies—not to mention a roof deck for summer hangs and a communal fireplace in the winter—for a weekend or extended stay.
Known for its vast namesake park that creates a natural border between upscale urban living and the beaches of Lake Michigan, Lincoln Park provides many reasons to visit. First, Lincoln Park Zoo, a 35-acre free zoo, sits right in the middle of the park and is home to hundreds of animals from around the world. Next, you have world-class museums like the Chicago History Museum, where you can experience City on Fire: Chicago 1871, highlighting the Great Chicago Fire, and Vivian Maier: In Color, a photography exhibit from this lifelong nanny who left behind 100,000 images upon her death. At the Peggy Notebaert Nature Museum, immerse yourself among 1,000 free-flying butterflies from 40 species in the Butterfly Haven.
And then, from Wells Street to Armitage Avenue and Halsted Street, there’s fantastic shopping, entertainment, and restaurants. So when you want to shop, hit long-running local stores like the Spice House for high-quality pantry ingredients from around the globe, Art Effect for unique home items and gifts, wine and spirits at House of Glunz, Chicago’s oldest wine merchant dating back to 1888, and men’s and women’s fashion at Lori’s Shoes, Tie Bar, and Calvin Tran.
Lincoln Park entertainment includes the renowned improv comedy shop the Second City, world-class theater at Steppenwolf, and authentic blues at Kingston Mines. And then there’s the dining. You can go super high-end with the three-Michelin-star Alinea, where chef Grant Achatz and his team prepare multi-course avant-garde molecular gastronomy tasting menus, or at the one-Michelin-star neighbor Boka, featuring chef Lee Wolen’s seasonal American fare.
But Lincoln Park is home to countless restaurants offering every sort of cuisine, including California-inspired at Summer House Santa Monica, Sichuan at Chengdu Impression, upscale Middle Eastern (with some of the fluffiest house-made pita you’ve ever had) at Galit, and the Athenian Room for Greek, which also happens to be a favorite of Tina Fey. And if you want to just relax, stroll among the mansions and historic brownstones of the Old Town Triangle area.
The Hotel Lincoln
Book now: from $96/night, expedia.com
The Hotel Lincoln, directly across from Lincoln Park, offers sweeping 360-degree views—not to mention great cocktails and bites—from its rooftop bar, the J. Parker, or an intimate sushi omakase meal in a hotel room at Sushi Suite 202.
Technically two separate neighborhoods divided by North Avenue, the area has generally gotten grouped together since its rise in popularity in the early ’90s when such artists and musicians as Liz Phair and Urge Overkill gathered here, especially at bars like the Rainbo Club and rock venues like Subterranean.
Over the past two decades, the neighborhood has gentrified (just walk along the 606, a 2.7-mile elevated nature-lined trail, to see the newer homes and renovated condo buildings), but what has remained are hip independent shops like Una Mae’s, for a mix of vintage and contemporary men’s and women’s clothing, candles, apothecary, and more; Myopic Books, one of Chicago’s best selections of new and used books—we’re talking 60,000 books stacked on those old wooden shelves; and Asrai Garden for stunning floral design, jewelry, scents, and other distinctive offerings.
While you make a day of strolling and shopping, stop at Antique Taco for blood orange margaritas and crispy tempura cod or barbecue pork carnitas tacos, wood-fired pizza and meats at Etta, elevated Spanish fare at Mama Delia, classic red sauce Italian at Club Lucky, house-made pasta at Tortello, Costa Rican at Irazu, Southern-style tamales at the Delta, modern Filipino at Cebu, or seasonal tasting menu fare at the Bristol. The options are plentiful so wander until you find what grabs you.
Book now: from $120/night, expedia.com
The hip Robey hotel, a former art deco office tower that dates back to 1929, modernized into a cool boutique spot with rooms featuring luxe linens, Le Labo bathroom products, and modern furniture. It also offers Café Robey on the ground floor with daily brunch, the Lounge on the second floor for coffee, drinks, and a place to get some work done, and two rooftop bars: the Up Room for sophisticated mixology and the Cabana Club, set around a pool, perfect for summertime frolicking.
While Germans, Irish, and Bohemians first settled the area, Pilsen has been an enclave for Mexican immigrants since the 1950s and those influences are felt deeply throughout the neighborhood. Stroll 16th Street to view dozens of murals (and many more that dot the neighborhood) depicting Mexican American heritage from local artists like Hector Duarte, Deliliah “Zena” Salgado, and Alejandro Medina.
The strong artist community attracted works from other acclaimed street artists, including Hebru Brantley and Jeff Zimmerman. Even more Mexican works appear at the National Museum of Mexican Art, home to one of the nation’s largest collections of Mexican art. But a visit to Pilsen would not be complete without eating. You can easily just eat high-quality Mexican fare with chilaquiles, chile rellenos, pollo en mole, and carne asada at La Esperanza; tamales, ceviche, and tortas at 5 Rabanitos; or some of Chicago’s most celebrated pork carnitas and chicharrones at Carnitas Uruapan.
Or explore other global flavors with chef Stephen Gillanders’s Asian-inspired American fare at S.K.Y.; French Vietnamese at HaiSous Vietnamese Kitchen from celebrated chef Thai Dang; or farm-to-table seasonal tavern fare at Dusek’s. Either way, eating in Pilsen always satisfies.
If you want to stay in Pilsen, you can find some good options on Airbnb, but if you’re looking for a hotel, the historic Blackstone on Michigan Avenue overlooking Grant Park or the modern Marriott Marquis at McCormick Place are both within two miles of Pilsen.
Book the Blackstone: from $129/night, expedia.com
Book the Marriott Marquis: from $224/night, expedia.com
For a true experience of culture and history in Chicago, head south to Hyde Park, home to the World’s Columbian Exposition in 1893 (which spawned the Garden of the Phoenix and Museum of Science and Industry, where you can see a full-size submarine and go down into a coal mine) and Kenwood, home to some of Chicago’s grandest homes, including one belonging to Barack and Michelle Obama.
This neighborhood is home to the University of Chicago and its striking Gothic campus, first designed by renowned architect Henry Ives Cobb and then added to by Eero Saarinen and Ludwig Mies van der Rohe and others for a modern feel. The famed Frank Lloyd Wright Frederick C. Robie House sits on the campus, and you can take in one of the best views of the Chicago skyline from Promontory Point.
Hyde Park has long been a center of Black culture in Chicago with the DuSable Museum of African American History but also with food at Virtue, a heralded Southern restaurant from famed chef Erick Williams, or Jamaican jerk chicken at Ja’Grill. Catch an array of live music—rock, electronic, dance, jazz, and more—at the Promontory.
Book now: from $229/night, expedia.com
The Sophy, a boutique hotel, sits along 53rd Street near many restaurants and shops, like the Silver Room, owned by another Eric Williams, who is opening the Bronzeville Winery just north of Hyde Park in the historic neighborhood of Bronzeville.
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