Chicago has around 80 unique neighbourhoods, which makes it one of America’s meccas of cultural diversity. Each community has a distinct personality and has something special to offer for first-time visitors. Thanks to an extensive public transport network, you can easily get around many of Chicago’s exciting districts. However, don’t be surprised to find enough activities in each area to keep you entertained for days.

    Then, which neighbourhood of Chicago is best for you? Read on as we’ve scanned through each section of Chicago and listed our favourite neighbourhoods to visit. From popular attractions and top-rated bars and restaurants to public transport access, these neighbourhoods are incredible hosts for your trip to the “Windy City.”


    River North

    For the Chicago Riverwalk and a cool nightlife scene

    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. The nearby Magnificent Mile on Michigan Avenue is Chicago’s shopping paradise. It hosts hundreds of retailers, upscale outlets, and stylish hotels.

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    Colourful streets bustling with rich Latino culture

    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. Pilsen also houses the famous Thalia Hall, which regularly hosts touring musicians, comedians, and DJs.

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    photo by Adam Jones (CC BY 2.0) modified


    Hyde Park

    A Chicago neighbourhood rich in local history

    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. Just a short walk away, the University of Chicago campus is known for producing some of the world’s most brilliant minds.

    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. 

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    West Loop

    A former industrial zone and Chicago foodie’s paradise

    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. Girl & The Goat, Bandit, and La Josie are just a few of the many world-class establishments on Restaurant Row.

    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 and learn about Greek culture at the National Hellenic Museum.

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    Old Town

    For some of the most historic buildings in Chicago

    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.

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    For great baseball and a bustling arts scene

    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 that appeals to many taste buds. From Italian and Chinese to Korean-Polish fusion, this neighbourhood lets you enjoy flavours from across the globe.

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    photo by Victor Grigas (CC BY-SA 3.0) modified



    The site of Chicago’s 20th-century Harlem Renaissance

    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. The South Side enclave is home to the Bronzeville Art District, where you'll find 6 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.

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    photo by Victor Grigas (CC BY-SA 3.0) modified



    The USA's first official gay neighbourhood

    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. Just a few minutes away, the Belmont Harbor is a delightful launching pad for sailing excursions on Lake Michigan. Sports fans can visit Wrigley Field to catch Chicago Cubs baseball games.

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    photo by Richie Diesterheft (CC BY 2.0) modified


    Wicker Park

    Chicago’s biggest hipster enclave

    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 2.7-mile bike and jogging path adorned with public art.

    Spend a few hours roaming the streets and you’ll find all sorts of bookshops, record stores, and unique eateries. You can kick off your evenings lounging at trendy cocktail bars. A popular option is The Robey hotel's rooftop bar. Continue the fun late into the night with your choice of rocking music venues, dance clubs, and dive bars.

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    Logan Square

    Beautiful architecture and spacious boulevards

    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 and a year-round Sunday farmer’s market.

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    photo by Thshriver (CC BY-SA 3.0) modified

    Daniel Grenier | Contributing Writer

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