A quick-fire guide to 7 can’t-miss Chicago neighborhoods

Some 77 official neighborhoods, each with their own personality, make up the patchwork of Chicago. But in a city with everything from walkable lakefront oases to late-night party havens, it can be hard for travelers to know where to start.

Below, we’ve gathered seven must-visit neighborhoods to check out on your next trip. Together, they paint a rich portrait of the city’s history, architecture, and culture—with some ridiculously fun Pride parades and some really great places to eat thrown in, too.

Northwest of Downtown Chicago, gritty Wicker Park has long been a creative hub for artists, musicians, and writers. In recent years, the neighborhood has added hip boutiques, buzzy restaurants, and design-forward hotels like the retro Robey Chicago to the mix.

To glimpse the neighborhood’s transformation—and take in industrial relics and shiny new residential development alike—rent a Divvy Bike (a Chicago bike-sharing program) and take a spin down the 606 recreational trail, which slices through the neighborhood on an elevated former rail bed.

Music fans will be in good company here. One can’t-miss stop for rock deep-cuts, according to longtime neighborhood resident Terry Alexander, is Reckless Records: “There’s no better record store in Chicago,” he said.

Alexander, also a partner in One Off Hospitality, which operates neighborhood restaurants like Big Star and Dove’s Luncheonette, has a crystal-clear Wicker Park rec: “If I had to choose my last meal, it would be sitting at the Rainbo Club with a cold Guinness and a cheap shot of whiskey in front of me,” he said.

Boystown—the Pride-flag-lined, mile-long stretch of North Halsted Street running between Belmont and Addison—is flanked by an eclectic array of LGBTQIA+-owned shops, restaurants, and bars. But travelers of all gender identities and sexual orientations are welcome in Boystown, the seat of the queer community in Chicago and the first officially designated gay neighborhood in the U.S.

“It’s a vibrant and inviting place to eat, shop, and socialize,” said Kevin Barbeau, the executive director of Northalsted Chamber of Commerce. But Boystown is also “an important reminder of past and present struggles—as well as successes—in achieving equality and acceptance,” he said.

By day, this area sees a steady thrum of foot traffic, and the Legacy Walk, a series of 40-rainbow-ringed pylons devoted to international LGBTQIA+ pioneers (from the writer Oscar Wilde to the astronaut Sally Ride), is a great way to take it all in. By night, it’s party time; do as the locals do and bar-hop on the strip—the rooftop deck at the sprawling Sidetrack (the largest gay bar in the Midwest) and the drag shows at Kit Kat Lounge are both cherished favorites.

Annual street festivals, including the Chicago Pride Fest in June and the Northalsted Market Days in August, draw revelers of all stripes, from the lavishly dressed to the nearly naked—and everything in between.

When Chicago forced Black Americans fleeing the Jim-Crow South to live in the red-lined, racially segregated South Side district, the area was disparagingly nicknamed the “Black Belt.”

“The residents, wanting a degree of dignity, renamed themselves and affectionately called it Bronzeville,” said Dawn Turner, a fourth-generation Bronzeville native and the author of the memoir Three Girls from Bronzeville.

Today, that history can be felt in the neighborhood’s art. Turner’s favorite piece is the Monument to the Great Northern Migration, a towering bronze sculpture featuring a person with a suitcase in hand, facing north: “moved forward by that promise that this land will offer something better,” she said.

Bronzeville’s contemporary-art scene is also worth exploring; the acclaimed Gallery Guichard, for example, specializes in rotating exhibitions by global artists from across the African Diaspora.

And to dine out here is to experience some of the many cultures and communities that call the neighborhood home. Dig into everything from Senegalese braised yassa chicken at Yassa African Restaurant to American Southern comfort food—including a “hangover plate” of fried chicken and grits—at Peach’s Restaurant.

Imagine 1,200 acres on Lake Michigan filled with tranquil parks and surrounded by leafy, townhouse-lined streets. Now plop a zoo smack dab on its eastern edge: That’s Lincoln Park.

One of few free zoos in the country, the Lincoln Park Zoo has nearly 200 animal species, and it’s part of a string of parks along the lakefront that allow cyclists, runners, and walkers to transit nearly the entire length of the city along the 22-mile Lakefront Trail. In summer, take the path to North Avenue Beach, Lincoln Park’s most bustling stretch of sand, for swimming or beach volleyball.

Next to the zoo are the grand greenhouses of the Lincoln Park Conservatory—the tropical rooms are a nice break from Chicago’s famous wind. And in the Peggy Notebaert Nature Museum’s Butterfly Haven, the dazzling swallowtails and lacewings are known to fulfill the “social butterfly” moniker, often landing on the shoulders of visitors.

Modeled after a wall in Beijing, the street-spanning Chinatown Gate heralds your entry into this 30-block neighborhood, which is best explored on foot.

“It’s not just a tourism attraction but a place for Chinese residents to visit social service agencies, have dim sum, and purchase Chinese groceries,” said Ben Lau, the executive director of the Chinese American Museum of Chicago, noting that visitors will almost certainly hear more Chinese than English.

There’s lots of art and architecture to take in here, from the Nine Dragon Wall, a relief sculpture depicting sacred dragons to the Pui Tak Center down the street, a former community center whose roof is clad in colorful terracotta tiles: red for joy and green for affluence.

There’s lots of food to take in as well, and you’d be hard pressed not to visit without an appetite. Dig into dim sum from MingHin Cuisine, one of Lau’s favorites (beloved by Tripadvisor reviewers for its pork buns and shrimp dumplings), or the rolling carts at Phoenix. For a dessert—and a few sweet and savory souvenirs—head to Aji Ichiban for a dizzying array of imported candy.

An independent village that was roped into Chicago when the city hosted the 1893 World’s Columbian Exposition, Hyde Park is an intimate neighborhood “where the best of the city comes together,” said Anthony Beach, the general manager of the Sophy Hyde Park hotel.

“It’s diverse, creative, entrepreneurial, architecturally significant, and it has a vibrant food scene,” he said, calling out the Museum of Science and Industry and the future Obama Presidential Center, which is slated to open in 2025 with a museum, community center, sprawling garden, and more.

The Sophy sits on 53rd Street, Hyde Park’s downtown corridor, along with shops like Silverroom, which sell graphic tees and hosts community-building readings and tango nights, and Suuri Design, where you’ll find jewelry designed by a local mother and daughter duo.

Any stroll in Hyde Park is an impromptu architectural tour. Walk a few blocks south from 53rd Street and you’ll see the University of Chicago’s neo-Gothic quads. Or, take a guided tour at the nearby Robie House, one of Frank Lloyd Wright’s Prairie School landmarks.

The city’s central business district, the Loop may not feel as cozy or culture-filled as other neighborhoods on this list. But a quick-fire visit means you can hit up much of Chicago’s top museums and iconic architecture in one go, plus Millennium Park (home to Anish Kapoor’s iconic “Cloud Gate,” AKA “The Bean,” a sculpture that’s just about as “Chicago” as it gets.)

Ariella Gibson, the marketing manager of the Chicago Loop Alliance, puts it succinctly: “The heart of the city is in the Loop,” she said.

You could spend your whole life in Chicago and still find new things to see at the Art Institute of Chicago, and it’s an absolute can’t-miss for visitors as well. The museum is known for its Impressionist masterpieces by the likes of Renoir and Seurat, as well as quirky exhibits like the Thorne Miniature Rooms, which feature dollhouse-size versions of residential interiors.

And although there are plenty of generic glassy towers in the Loop, there are also landmarked buildings that are staggering to see, including the Chicago Cultural Center (home to the world's largest Tiffany stained-glass dome) and 330 North Wabash, designed by the groundbreaking midcentury architect Ludwig Mies van der Rohe.

To get a sense of the city’s unique architectural makeup, take a walking tour with the Chicago Architecture Center (which, as Tripadvisor reviewers point out, grants access to some pretty jaw-dropping building lobbies) or grab your seat on Shoreline Sightseeing’s architecture-themed river cruise, which has more than 3,700 five-star reviews.