Feb 14, 2024 - Culture

Visit the most romantic streets in Chicago

A man walks his dog in the middle of a shaded, beautiful Chicago street.

Alta Vista Terrace in Wrigleyville. Photo: Monica Eng/Axios

Who needs dimly lit restaurants or romantic getaways when Chicago already has the perfect backdrop to make your valentine feel special?

The big picture: There are so many beautiful streetscapes to visit around the city. Here are the top 10 most romantic sections of streets in town.

📍 Alta Vista Terrace (Wrigleyville)

Built 120 years ago, this little street just northeast of Wrigley Field is hella romantic. The homes are inspired by row houses in London. This is a perfect place to pop the question or just marvel at unique Chicago architecture.

📍 West Caton Street between Milwaukee and Leavitt (Wicker Park)

Old graystones on tree lined street
Photo: Carrie Shepherd/Axios

Take a nostalgic stroll down Chicago history in Wicker Park. The historic houses scream romance.

📍 Glenwood Avenue (Rogers Park)

Photo of a street
Photo courtesy of the Rogers Park Business Alliance

Near the old Heartland Cafe and nestled next to the Red Line tracks, this charming stretch of Glenwood Avenue is perfect for a romantic stroll. If you listen closely, you can hear poetry from the defunct No Exit Cafe.

📍 West Jackson Boulevard between Ashland and Laflin (West Loop)

Photo of a street
Photo: Justin Kaufmann/Axios

The tree-lined boulevard and old-school Chicago architecture make this particular block a hidden gem on the Near West Side.

📍 57th between Kenwood and Woodlawn (Hyde Park)

Photo of people walking on street
57th Street Books. Photo: Dina Rudick/The Boston Globe via Getty Images

Frankly, all parts of Hyde Park are pretty romantic, but the stretch of 57th Street that includes Medici and 57th Street Books is a great place to start.

📍 Lincoln Avenue Adler and Sullivan Row Houses (Old Town)

Photo of houses on the street
Photo: Justin Kaufmann/Axios

Walk down North Wells Street and turn left onto Lincoln Avenue to enjoy awe-inspiring Adler & Sullivan architecture. You'll get lost (in your loved one's eyes) exploring the surrounding neighborhood.

📍 Armitage Avenue between Halsted and Sheffield (Lincoln Park)

Photo of a man standing on a street
Armitage Avenue in Lincoln Park. Photo: Justin Kaufmann/Axios

This little stretch in Lincoln Park has been taken over by national chains, but there is no denying the beauty on display. The ornate architecture of the old houses, as the L train whizzes past, is a work of art.

📍 Wilson and the Chicago River (Ravenswood Manor)

Mural painted on a wall leading to a bridge.
Photo: Monica Eng/Axios

We don't have too many canals in the Chicago area that would fall under a romantic category, but the bridge on Wilson over the river is a treat on the Northwest Side.

📍 Central Park Avenue at Garfield Park Conservatory (Garfield Park)

Photo of a conservatory next to a street
Photo: Carrie Shepherd/Axios

The curve of the street hugs the lush, green landscape and highlights the conservatory's glass dome, drawing you in. Plus, the vintage L platform makes this West Side spot feel like a stroll through the past.

📍 South Shore Drive and South Shore Cultural Center (South Shore)

Photo of a cultural center
South Shore Cultural Center. Photo: Saul Loeb/AFP via Getty Images

DuSable Lake Shore Drive gets honorary mention when we talk about romantic spots. When the drive takes a turn at 71st Street in front of the South Shore Cultural Center, you get a nice stretch of housing and businesses that are beyond comparison.

  • Stop by the Rainbow Beach or walk the grounds of the famed South Shore Cultural Center, where the Obamas celebrated their wedding reception.
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