12 Most Popular Neighbourhoods in Chicago

River North places you in the centre of the action near Chicago’s central business district. With sprawling clubs and bars around every corner, the enclave is one of the city’s hottest late-night hangouts. Unwind with a fabulous dinner in chic restaurants like RPM Steak, then crank up the energy after sunset at The Underground, Spybar or other pulsating nightclubs.

To gaze at beautiful architecture, River North impresses with its array of stunning buildings. Head to the scenic Chicago Riverwalk to check out masterpieces like theMART, the Wrigley Building and Marina Towers. For retail therapy, head to Chicago’s shopping paradise, Magnificent Mile on Michigan Avenue.

Pilsen in Chicago’s Lower West Side captivates your senses with elaborate murals, delicious eateries and cheerful music. The primarily Mexican-American neighbourhood earns praise for its food and art scene that’s undoubtedly among the best in Chicago. Check out the National Museum of Mexican Art to browse through 10,000 pieces of Mexican heritage. Outside the museum, you'll find murals designed by revered street artists.

The moment you step off the decorative 18th Street Station on CTA’s Pink Line, you feel the exciting buzz of the enclave. Food vendors sell tacos and elotes (grilled sweet corn) on the streets, while family-owned eateries serve authentic Mexican dishes. Check out the famous Thalia Hall, which regularly hosts touring musicians, comedians and DJs.

Hyde Park plays an important role in Chicago's history and has several world-famous attractions. This South Side neighbourhood gained fame for hosting the Chicago World’s Fair in 1893. A must-visit for families is the spectacular Museum of Science and Industry.

Siting on the shores of Lake Michigan is Jackson Park, a 500-acre public space with a sprawling bike and running path, radiant gardens, and sandy beach. Other notable institutions include Frank Lloyd Wright’s Robie House, DuSable Museum of African American History, and Hyde Park Art Center. Hyde Park is also the former home of Barack Obama, so make sure to swing by some of his favourite spots while you're in the neighbourhood. 

Head to West Loop if you came to Chicago on an empty stomach as it’s where you’ll be able to enjoy a feast. You won’t need to stray far from Chicago’s central business district to find many of the city’s top restaurants. Randolph Street, known as Restaurant Row, features some of the hippest eateries in Chicago and draws hordes of hungry patrons.

Up the block, Fulton Market is an old warehouse district that houses upscale restaurants, cocktail bars, cosy cafés and laid-back breweries. The nearby Greektown is a great place to have a meal at authentic tavernas, restaurants or pastry shops. To learn about Greek culture, head over to the National Hellenic Museum.

Old Town in Chicago’s North Side contains some of the city’s most historic buildings. St. Michael’s Church is among the city's oldest structures. It miraculously survived the Great Chicago Fire of 1871. Established in 1958, Old Town Ale House is a rowdy dive bar famous for its eye-popping wall art. Elsewhere, the swanky neighbourhood is known for boutique shops, fancy restaurants and luxurious homes.

The Second City comedy club is known for hosting world-renowned comedians like Bill Murray, Chris Farley and Steve Carrell. Swing by for a live show any night and watch the rising talent in the comedy scene. Don’t forget to wander down Wells Street to visit some of Chicago’s beloved bars and restaurants.

Bridgeport is home to the Chicago White Sox and attracts baseball fans to Chicago’s South Side. An easy journey on the CTA Red Line to the Sox–35th Station drops you off beside Guaranteed Rate Field. Outside of the baseball scene, Bridgeport has multiple thriving arts venues. Some of the top places to visit include the Bridgeport Art Center and Zhou B Art Center.

Chicago’s lakeside location gives it a rich maritime tradition, with the Chicago Maritime Museum displaying thousands of seafaring objects. Bridgeport is also one of Chicago’s most diverse areas and features an eclectic food scene, from Italian and Chinese to Korean-Polish fusion. Bring your appetite and travel across the globe without leaving Chicago.

Bronzeville is the lifeblood of African-American culture in Chicago and has produced some of the city’s famous icons. Jazz musician Louis Armstrong, Pulitzer Prize-winning poet Gwendolyn Brooks and civil rights leader Ida B. Wells made remarkable impacts on the neighbourhood. Bronzeville is home to the Bronzeville Art District, where you'll find stunning visual art spaces showcasing the community’s incredible history.

Venture down Martin Luther King Drive to check out the Bronzeville Walk of Fame and Monument to the Great Northern Migration. The Bud Billiken Parade is the largest African-American parade in the USA. Held every summer for nearly a century, it's an exciting celebration filled with music, dance and food. So, make sure you have your camera ready.

Boystown made history by becoming the USA's first gay enclave to be recognised by a city government. Located inside Lakeview, the vibrant neighbourhood is home to much of Chicago’s LGBTQ history and LGBTQ-owned businesses. Walk around the rainbow-coloured streets to visit cheerful bars, unique eateries and vintage shops. Don’t miss the Legacy Walk that celebrates LGBTQ+ icons and historic events for the community.

The neighbourhood becomes especially lively during Chicago’s annual June Pride Parade. Watch the vibrant nightlife scene come to life with energetic nightclubs, drag shows and stylish bars. The Belmont Harbor is a delightful launching pad for sailing excursions on Lake Michigan. If you’re a sports fan, visit Wrigley Field to catch Chicago Cubs baseball games.

Wrigleyville is a Chicago neighbourhood that’s good to visit for live sports and good time fun. The lively Northside neighbourhood’s main attraction is the historic Wrigley Field. Whether or not you’re a baseball fan, there’s no better way to spend a summer afternoon than cheering for the Chicago Cubs. Join an official Wrigley Field Tour if you’re keen to learn more about Chicago’s 100-year baseball history.

Surrounding the field, the pocketed community brims with shops, sports bars and restaurants, especially along Clark Street. To hear the echoes of the voices of Bob Dylan, Nirvana and other legends, check out who’s playing at the legendary Metro music hall.

Wicker Park is known as the epicentre of hipsterdom in Chicago, thanks to its art galleries, hip cafés and vintage stores. You can reach this enclave by riding the CTA Blue Line and hopping off at Damen Station. It greets visitors with quirky attractions seen nowhere else. The signature sight is the 606, an old railroad converted into a bike and jogging path adorned with public art.

Spend a few hours roaming the streets and you’ll find all sorts of bookstores, record stores and unique eateries. You can kick off your evenings lounging at trendy cocktail or rooftop bars. Continue the fun late into the night with your choice of rocking music venues, dance clubs and dive bars.

Gold Coast is a serene, upscale neighbourhood north of Downtown Chicago and a few blocks from Lake Michigan. Since the late 1800s, the district has attracted Chicago’s glitziest and wealthiest residents. As a result, the tree-lined streets are dotted with designer boutiques, prestigious 19th-century homes and renowned restaurants.

With pedestrian-friendly sidewalks, you can explore the area with ease. Notable buildings in the area include the Former Playboy Mansion and the Charnley-Perksy House, designed by Louis Sullivan and Frank Lloyd Wright. In the evening, head to Rush Street and mingle with the city’s trendy crowd at lively bars.

Logan Square sits right off the CTA Blue Line in Chicago’s West Side. Wander down Logan Boulevard to admire stately mansions, historic churches and the towering Illinois Centennial Monument. The nearby Logan Theatre dates to 1915 and enchants movie buffs with its retro décor. Watch indie films, unwind in the lounge or visit during the Chicago Underground Film Festival.

Logan Square's lively nightlife scene consists of upscale cocktail bars, vibrant music venues and craft breweries. Best Intentions is one of Chicago’s top-rated watering holes, while Logan Square Auditorium hosts all sorts of public events. The neighbourhood also spoils visitors with a diverse food scene. Remember to check out the year-round Sunday farmer’s market.