Discover a world of cultures across Chicago’s many neighborhoods

Destination Illinois

CHICAGO — Chicago is known as a city of neighborhoods, and there’s plenty to do across its 77 community areas, each with a unique personality of its own. 

Begin your adventure rolling down the bike lanes along the “Hipster Highway” of Milwaukee Avenue in Wicker Park, an always electric scene, even as nightclubs are shuttered during the pandemic. 

Discover new shops along the street, and duck into Cebu for some Spanish and Chinese influenced eats. Gobble up Filipino egg rolls, known as “Lumpia,” stuffed with tender roast pork, carrots, garlic and onions and dipped in dark mushroom soy sauce.        

Wash it down with Cebu’s version of the mojito, blending Passion Fruit and El Dorado Rum for the perfect thirst quencher.

Kids love the pool on the top of the iconic Robey Hotel Chicago. The Art Deco elevators whisk you to the “Up Room” cocktail bar, featuring marvelous scenery sure to lift your spirits. Even the sunny guest rooms feature a spectacular view.

On the next leg of your neighborhood tour, feel the “calor” and warmth of the Puerto Rican people, like the Caribbean herself inviting you in for a swim.  

Even after organizing hurricane and earthquake relief efforts for those on the island,  this big-hearted Chicago community is pulling together to defeat the pandemic.   

Nothing stirs the soul like rhythm, drawing people to the irresistible neighborhood recently renamed “Puerto Rico Town.”

The coffee’s strong at Café Colao, one of many restaurants featuring sidewalk cafes. 

Some of them serve up the legendary “Jibarito,”’ a sandwich invented in Chicago featuring seasoned steak, onions, garlic and avocado sandwiched between toasted plantains.

Educator and author Ada Lopez chronicles the journey for Chicago’s Boricua community.

“It’s a beautiful experience. You see the extended families, the grandparents with the children,” Lopez said.

Next, feel the romance of Chicago’s Little Italy. Long before social distancing, Italians mastered the art of “al fresco” dining.   

Community leader Ron Onesti’s family landed in 1911 and never left the neighborhood which has served as a port of entry for generations of Italian-Americans looking for a better life.

“So many businesses and so many families have tried to recapture the feel of what it was like being in Italy,” Onesti said. 

The Divino family is one of those that’s still part of the local community. Their Pompei Restaurant & Bakery serves up fresh pasta, salads with homemade Stromboli and pizza.  

“Taylor Street is one of those neighborhoods that’s truly based on family. This is a neighborhood of families,” Onesti said.

Grab it to go because we’re off to our next destination: bustling Hyde Park,  home to the University of Chicago, famous architecture and the reopened Museum of Science and Industry. 

You’ll feel the dynamic energy of this South Side community. 

“It seems that Hyde Park really was a microcosm but also a Mecca if you will for political activism and progressive politics,” said Perri Irmer, the CEO of the nearby DuSable Museum of African-American History.

Irmer points to groundbreaking leaders from Hyde Park: from Chicago’s first African-American Mayor Harold Washington, to Cook County Board President Toni Preckwinkle, the first female to lead the county’s Democratic Party, and a law professor and community organizer by the name of Barack Obama.

Retrace the steps of the 44th President of the United States from his Kenwood home at 50th Street and Greenwood Avenue, which is still under the watchful eye of the Secret Service and attracts the occasional selfie.  

Stop at Valois Restaurant on 53rd Street for steak and eggs, a favorite menu item. And at Hyde Park Hair Salon at 52nd Street and Blackstone Avenue, the presidential barber chair is encased in glass.  

“He was our guy. He’d come in and we’d talk sports, we’d talk local events,“ said barber Maurice McClain. “We’d have a crowd of people outside, as many as we could fit in the barbershop.”

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