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The Best Neighborhoods to Explore in Chicago

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The beating heart of the Windy City exists in its more than 200 diverse neighborhoods, positioned within 77 community areas and divided into nine districts: Central, Far North Side, Far Southeast Side, Far Southwest Side, North Side, Northwest Side, South Side, Southwest Side, and West Side. Chicago loves a grid. Keep reading to learn about some of the best neighborhoods in the city worth exploring.

01
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Andersonville

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Address

Andersonville, Chicago, IL, USA

Known for its Swedish roots and history as one of the city’s largest LGBTQ+ populations, Andersonville is where to go for shopping and dining in independent restaurants. Culture opportunities abound in this neighborhood. Visit the Swedish American Museum or shop for your next read at one of the largest independent feminist bookstores in America, Women and Children First. For fans of music and theatre, you can see modern drama at the Raven Theatre, be a part of an immersive show at the Neo-Futurist Theater, or hear a live chorus at Allegrezza, Later, grab a drink at one of the many bars or dance clubs—Farraguts, Hopleaf, Lady Gregory’s, Simon’s Tavern, and Replay Andersonville are all gems.

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Logan Square

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Address

Logan Square, Chicago, IL, USA

From May through October, Logan Square, one of Chicago’s oldest neighborhoods, is home to one of the best farmers markets in the city. But because there’s a strong art and music scene here, you’ll find that there’s really no bad time to visit. Flanked by limestone homes, Logan Boulevard cuts through the center of the neighborhood and is a good place to begin. Marvel at the Centennial Monument, see a movie at the historic Logan Theatre, hear live music at The Congress Theater or Concord Music Hall, and sip a cocktail at one of the many neighborhood bars.

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Pilsen

TripSavvy / Cory Giguere



Address

Pilsen, Chicago, IL, USA

Music and art thrive in this Latin-centric community. Street art, shopping boutiques, eateries, and the National Museum of Mexican Art bring visitors from all over the nation to this corner of the city. If you’ve ever wanted to line up to watch runners tackle the Chicago Marathon, Pilsen is one of the best neighborhoods to view the race—or to run through if you wish to compete yourself. You’ll hear loud music and crowds of people cheering, watch performers dance with noisemakers, and see all the local businesses and restaurants throw open their windows and doors. No matter what time of year you come, be sure to grab sweet noshes at Panaderia Nuevo Leon, a self-serve Mexican bakery.

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River North

TripSavvy / Cory Giguere



Address

River North, Chicago, IL, USA

Kitty-corner to Chicago’s central business district, River North is full of trendy bars, ideal for that after-work adult beverage or dinner (Eataly is a fun stop for its market full of wines and cheeses and small indoor restaurants). Architecture tours up and down the Chicago River are popular, as is shopping along the Magnificent Mile. Stroll along the Chicago Riverwalk and stop for a glass of wine at the City Winery. If you’re hankering for a slice of the city’s famous deep dish pizza, check out Lou Malnati’s, one of the city’s most beloved pizza joints. Hubbard Street, between LaSalle and North State Street, is a go-to nightlife destination in the neighborhood, while Navy Pier is just east of River North, on Lake Michigan.

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West Loop

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Address

West Loop, Chicago, IL, USA

Formerly an industrial area, the West Loop is now one of the trendiest neighborhoods in the city, full of Michelin-starred dining, shopping, boutique hotels, and nightlife. The high-end Oriole or Smyth restaurants are great places to take a date, as is the popular reserve-in-advance Girl and the Goat. Sweat and network at an indoor climbing gym, listen to live music at Bottom Lounge, or visit the Green City Market, Chicago’s biggest and original year-round sustainable farmers market. If you wish to make West Loop your base, we recommend booking a stay at SoHo House, The Godfrey Hotel, Hotel Julian, or The Langham, Chicago.

It’s worth noting that the Museum Campus—where you’ll find Adler Planetarium, Shedd Aquarium, Field Museum of Natural History, and Soldier Field—is just south of Grant Park in the South Loop neighborhood. The Art Institute of Chicago is directly east, on the north end of Grant Park.

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Wrigleyville

 TripSavvy / Cory Giguere



Address

Wrigleyville, Chicago, IL, USA

Wrigleyville, home of the Chicago Cubs, is a neighborhood like no other. Sports bars (the Cubby Bear is super popular, especially before or after a game) and souvenir shops surround the stadium, and a bunch of new hotels and restaurants have popped up since the Cubs clinched the World Series in 2016. View a game from the stadium or from the top of one of 11 rooftops, or indulge in a Wrigley Field tour for a behind-the-scenes look at this historic ballpark. Stay at Hotel Zachary at Gallagher Way—a new green space just outside the stadium—for great views of the ballpark and the “Wrigley Field Home of the Chicago Cubs” sign.

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Bronzeville

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Address

Bronzeville, Chicago, IL, USA

A hub for Black culture in Chicago, Bronzeville is the former home of Louis Armstrong, Gwendolyn Brooks, Bessie Coleman, Ida B. Wells, and Richard Wright. Check out the Harold Washington Cultural Center and Ida B. Wells—Barnett House before taking a trolley tour through the Bronzeville Art District (be sure to stop by the Blanc Art Gallery and Gallery Guichard). When the day is through, dine at one of the BBQ or soul food restaurants in the neighborhood. Don’t miss the Bud Billiken Parade, the largest African American parade in the U.S., held here the second Saturday of every August since 1929.

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Boystown

TripSavvy / Cory Giguere 



Address

Boystown, Chicago, IL, USA

Eleven pairs of 23-foot-high Art Deco rainbow pylons welcome you to this part of the city. Boystown, an enclave of the Lakeview neighborhood, is the colloquial name for the LGBTQ+ community that flanks North Halsted Street. While you’re here, visit the Center on Halsted, the Midwest’s largest LGBTQ+ community center. See improv or sketch comedy at The Annoyance Theatre and Bar, or a drag show at Kit Kat Lounge and Supper Club. Eat at the famous Chicago Diner, a vegetarian restaurant that’s been meat-free since 1983. The neighborhood lights up during the Chicago Pride Parade and Chicago Pride Fest, an annual event that happens here each June.

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Wicker Park

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Address

Wicker Park, Chicago, IL, USA

Hipsters love Wicker Park, a neighborhood full of coffee shops, vintage clothing boutiques, bars, and art galleries. Are you looking for an obscure record or ’80s nostalgia? You’ll find it here. At the heart of the neighborhood is the Six Corners area, where North, Milwaukee, and Damen Avenues intersect. Start on the 606, an elevated 2.7-mile rail line that has been converted into a multi-use recreational park and trail, one that winds through Wicker Park, Bucktown, Humboldt Park, and Logan Square. Have drinks at the semi-hidden (and swanky) The Violet Hour, sip espresso while you peruse the shelves at Volumes Bookcafe, and live out your movie-loving wistful dreams at The Wormhole. Stay at The Robey, where you’ll find excellent dining at Café Robey, plus rooftop views of the Six Corners.

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Old Town

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Address

Old Town, Chicago, IL, USA

On Chicago’s north side sits the historic neighborhood of Old Town. The Second City—the world-famous comedy club where Tina Fey, Stephen Colbert, and John Belushi have performed—is here, as is Zanies. Enjoy at drink at Old Town Pour House, which offers up one of the largest beer menus in Chicago, and follow it up with a trip to the family-owned The Fudge Pot, a chocolate shop that’s been in operation since 1963. You can also gain a deeper understanding of the Windy City’s past at the Chicago History Museum. North Avenue Beach and the Lakefront Trail are nearby.

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