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5 Chicago Neighborhoods to Explore on Vacation

Of Chicago's 77 diverse neighborhoods, these are the places locals love to hang.

U.S. News & World Report

5 Chicago Neighborhoods to Explore on Vacation

Photo provides a view of downtown Chicago, south loop residential area.

Enjoy both the new and old in Chicago's South Loop neighborhood.(Getty Images)

Chicago is a city of neighborhoods, many of them undiscovered by visitors. Venture beyond popular River North, Gold Coast, Old Town and Lincoln Park to these Chicago neighborhoods brimming with history, diverse dining, boutique shopping and eclectic entertainment. They're all less than 10 miles from the Loop and easily accessible via public transportation.

Wicker Park/Bucktown

If it's edge and esoterica you're after, find it in West Side sister neighborhoods Wicker Park and Bucktown.

"Explore by bike the funky storefronts, galleries and specialty restaurants on Milwaukee, Damen and North avenues," says Victor Colon, head concierge at The Langham, Chicago. Divvy bike-share stations abound along these three streets that intersect at the triangular Flatiron Arts Building, which harbors working artists' studios that are open to the public.

First Polish immigrants, then urban pioneers and starving artists paved the way for those now living in Wicker Park's restored brownstones and Victorians. But the gritty neighborhood's alternative vibe, pulsing when Chicago author Nelson Algren lived there through the 1970s, is alive. Established art galleries include Arc Gallery and Monique Meloche. Chopin Theatre hosts international movies and performances.

Old-school, still-cool Myopic Books bans cell phones. Store B Vintage and Buffalo Exchange specialize in retro fashion. Since 1921, Margie's Candies hand-dips chocolates and ice cream cones. Co-ed Russian banya Red Square has steamed and rubbed down Chicagoans since 1906.

Iconic music clubs Subterranean, Empty Bottle and Double Door rock all night. It's a perpetual party at honky-tonk taco joint Big Star, as well as at Piece Brewery and Pizzeria, and Emporium Arcade Bar. Swank speak-easy The Violet Hour crafts James Beard Award-winning cocktails.

Born and raised in Wicker Park, Bernard Runo, concierge supervisor at Sofitel Magnificent Mile Chicago, says, "My guilty pleasures are Furious Spoon ramen noodle shop and shopping for vinyl at Reckless Records where a scene in [the 2000 flick] 'High Fidelity' staring Chicago actor John Cusack was filmed."

South Loop

Gentrified blocks on the Near South Side preserve Chicago's history from its frontier days forward. Oversized guidebooklike plaques near sites make self-navigating the storied streets easy.

"Tour the Prairie Avenue Historic District to see gorgeous Gilded Age mansions of Chicago's rich founding families, mobster Al Capone's Lexington Hotel headquarters and Chess Records blues recording studio," says Mark Roberts, head concierge at the Thompson Chicago.

Docents lead tours of the 1836 Clarke House Museum, Chicago's oldest residence, and the elegant 1887 Glessner House Museum. Nearby, Second Presbyterian Church has Arts and Crafts murals and Tiffany glass windows.

The Printer's Row warehouse lofts once housed book binderies. In June, 150,000 page turners attend Printers Row Lit Fest, the Midwest's largest free outdoor bookseller-author event.


After the Great Chicago Fire of 1871, Swedish immigrant farmers established Andersonville. Today, the North Side family neighborhood is fertile ground for a full day of play.

"I love Andersonville for its cultural mix represented by the Swedish American Museum, restaurants and independent shops along Clark Street and Ashland Avenue," says Kristen Klus, head concierge at the Four Seasons Hotel Chicago.

Gethsemane is a lush greenhouse, garden and gift shop. Readers can browse feminist book store Women & Children First, while graphic novel fans might favor AlleyCat Comics. Find vintage goods and home decor at Brown Elephant Resale Shop, Andersonville Galleria and Woolly Mammoth Antiques & Oddities.

Craft beer bar Hopleaf specializes in Belgian brews. George's Ice Cream & Sweets shop scoops decadent sundaes. Good morning meals are guaranteed at M. Henry and Kanela Breakfast Club. Gay bar Hamburger Mary's dishes gourmet burgers.

Family-owned Svea Restaurant, Swedish Bakery and Prohibition-era Simon's Tavern keep Andersonville's charming ethnic heritage relevant, as do the annual St. Lucia Festival of Lights and Midsommarfest celebrations.


The Lakeview encompasses three microhoods for sports fans, foodies and shoppers.

Baseball fans beeline for ivy-cloaked Wrigley Field, the nation's second oldest Major League Baseball park, built in 1914, and den of the 2016 World Series Champion, curse-crushing Chicago Cubs. Reservations are required for guided daily ballpark tours.

"Wrigley Field creates a village within Lakeview steeped in Cubs culture experienced best at a game or watching one from a very different vantage point atop a surrounding building's rooftop," says Steve Grillo, head concierge at The Peninsula Chicago.

Southport Corridor shopping district landmarks are Julius Meinl Viennese coffeehouse and two restored, almost century-old entertainment venues: Music Box Theatre and Mercury Theater Chicago. Must-stop shops include Uncle Dan's Outfitters, M2 Boutique and Krista K Boutique. Southport Grocery and Cafe carries local food purveyors' products and griddles cupcake batter pancakes.

Both Schubas Tavern and Southport Lanes & Billiards, a bar, pool parlor and bowling alley still employing pin boys, were built by Schlitz Brewing Company almost 100 years ago.

Graceland Cemetery and Arboretum, established in 1860, warrants a self-guided tombstone tour. Roberts says, "Noteworthy Chicagoans buried here include Daniel Burnham, George Pullman, Potter Palmer, Marshall Field, boxer Jack Johnson and 'Mr. Cub' Ernie Banks."

Hyde Park

No neighborhood exercises your noggin like Hyde Park. The South Side lakefront enclave has many museums and encompasses the historic 1893 World's Columbian Exposition fairgrounds.

"Choose from the colossal Museum of Science and Industry, the DuSable Museum of African American History and, on the University of Chicago campus, the Oriental Institute, Smart Museum of Art and Robie House," says Tim Batchelder, head concierge at The Talbott Hotel.

The campus' Frank Lloyd Wright-designed Robie House is a National Historic Landmark. When President Barack Obama was a professor in the law school, he frequented labyrinthine 57th Street Books, cafeteria-style Valois Restaurant and pizzeria Medici on 57th. His family home is in the adjacent Kenwood community.

Neighborhood events include the Hyde Park Jazz Festival, 57th Street Art Fair and African Festival of the Arts. Relieve cultural brain freeze with lake breeze at 57th Street Beach and peaceful Promontory Point.

To experience more of what Chicago has to offer, check out the U.S. News Travel guide.

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