Travel Tips

America’s Gypsy: Puerto Rico in Chicago

Locations in this article:  Chicago, IL Los Angeles, CA

Ana Berry, America’s Gypsy, Puerto Rico in Chicago“America’s Gypsy” Ana Berry travels the world within America and always seems to find cultural adventures waiting just around the corner. Today, she takes us on a journey to Puerto Rico in Chicago.

It was a cold and rainy day in Chicago and I needed some warmth.

Driving northwest on Division Street and flipping through the radio, I came across SalSoul 98.5 FM, Chicago’s local Puerto Rican station. The sounds of salsa vieja (old salsa) filled the air and the memories of my recent trip to Puerto Rico flooded my mind.

As I passed Western Avenue, I could already smell the tostones in the fry pan and hear the coqis chirping in the trees.

Division Street, in Chicago’s Humboldt Park neighborhood, is the symbolic center of the city’s Puerto Rican community. Massive 59-foot steel sculptures of the Puerto Rican flag  adorn both sides of the street and culturally signify the entrance into Paseo Boricua (Gateway to Puerto Rico).

Puerto Rico Chicago Mural

Puerto Ricans have been moving to Chicago since the 1920s. In the early 1960s a group of Puerto Rican civic leaders in Chicago called “Los Caballeros de San Juan” organized the first unofficial Puerto Rican parade. They soon joined with the Chicago Park District and created the annual week-long festival of Boricua art, music, food and culture that’s centered around the 207-acre Humboldt Park.

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Dance Academy of SalsaLooking down at my feet while walking along the Paseo Boricua, I imagined I was on a parranda (a Puerto Rican tradition similar to Christmas caroling) through the cobblestone streets of viejo San Juan, sipping on Don Q rum and singing “Feliz Navidad.” The best I could do was dance in my boots on my way to the 5 p.m. class at the nearby Dance Academy of Salsa (

I was greeted by a chorus of smiling “holas” and was soon wrapped in the arms of a sun-kissed man twirling me to the sounds of salsa. After an hour of 1, 2, 3 … 1, 2, 3 … turn, I was sweaty from the songs of amor … yet still hungry for more!

La Bruquena restaurantContinuing my parranda along the Paseo Boriqua, I cha-cha-ed across the street to the restaurant La Bruquena for an authentic Puerto Rican dinner. La Bruquena, named after the crab indigenous to Puerto Rico, has been in existence since the 1940s and specializes in the best of fried “everything!”

I indulged in my favorites: tostones (seasoned fried green plantains), a jibarito (a sandwich made with flattened, fried green plantains instead of bread and stuffed with meat), and mofongo (the signature dish of Puerto Rico, made from mashed plantains, seafood and vegetables).

When in Puerto Rico proper, I can never seem to get enough plantains, but this time I definitely went a little bananas!

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After finishing that heavy meal, I needed a digestive! And what better way to quench my thirst and aid my digestion than aqua de coco (cold coconut water known for its cleansing and cooling properties)?

Puerto Rico in Chicago streetIn Puerto Rico, there are fruit stands on every street corner stocked with chilled coconuts fresh from the trees, so I hoped to find something similar in the park of the Paseo Boriqua.

Walking towards Humboldt Park, I was accompanied by reggaeton music blasting from each little bodega on La Division (the name for Division street in local parlance) as I passed thoroughfares named in honor of notables such as former governor of Puerto Rico, Luis Muños Marín, and nationalist leader Pedro Albizu Campos.

On the corner of the park I found exactly what I was looking for: three stations of trucks filled with large juicy watermelons, cherries and coconuts.

Humboldt Park StandThey cut the top off a big coconut and stuck a straw in it for me to enjoy.

The sun had set and my quick cultural vacation for the day seemed to be over. On my way back to my car, I passed several vibrant murals on the large brick walls. One that stuck out in particular was a painted image of giant hands clasped tightly together over a child’s coffin. The hands stood tall next to protesters and rioters with the words above them: Unidos Para Triunfar (Together We Overcome).

The image on the mural reaffirmed the importance of continuing one’s cultural traditions over generations, even if it’s in a new land.

Hear the sounds and see the sights of the area with Ana Berry as she journeys through Puerto Rico in Chicago in this video…

Puerto Rico ChicagoCrossing oceans and starting anew only deepens the appreciation of one’s homeland. It always seems that memories of families and friends surpass the hardships life will always bring.And although I was walking down Division Street in the heart of America, for a few hours of my day, I felt united with Puerto Rico.

By Ana Berry for Visit Ana on the Web at and

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