Two of the Prettiest Neighborhoods in Chicago

November 8, 2021 | By Lauren Bozarth
Reading Time: 3 Minutes

Old Town and River North are considered two of the prettiest neighborhoods to live in but for vastly different reasons. Let’s see how these two gorgeous downtown Chicago communities compare.

Two of the Prettiest Neighborhoods in Chicago

old town apartment buildings

Old Town

There is no denying the charm that the Old Town neighborhood offers. Walking down the tree-lined streets, you’ll stumble across stunning Victorian-style homes, quaint narrow streets, and adorable local shops.

You can see traces of Old Town’s history in much of the classic architecture, especially around the Old Town Triangle.

The history of Old Town explains where a lot of its charm came from. After the Great Chicago Fire in 1871, the Old Town Triangle was one of the only surviving areas. Afterward, it began to grow, initially attracting many artists and even playing a part in World War II. After the war, the area was known as “North Town” and began hosting art fairs called “Old Town Holiday.” Eventually, the name evolved into its current name, “Old Town.”

In the late 1970s, the City Council of Chicago designated most of the Old Town Triangle a Chicago Landmark to preserve the architectural and historic character of the area. 

Some of the most iconic buildings are still standing here, including St. Michaels Church and the Second City. You can also find plenty more beautiful old buildings that have been around since before the disaster.

River North

River North is equally as magical as Old Town but in a unique way. Many people are enchanted by the downtown neighborhood’s ultra-hip and ultra-urban setting. 

The countless shiny skyscrapers and sleek art galleries tucked away into old warehouse buildings are bound to impress.

River North’s gallery district has attracted plenty of creatives and remains a charming area within the neighborhood. This district emerged during the late 1970s when artists and dealers found themselves drawn to the expansive and dynamic spaces offered by the neighborhood’s former manufacturing buildings. 

Now, the area houses the largest concentration of art galleries in the United States after Manhattan.

As its name implies, River North is located right along the beautiful Chicago River. Tourists and residents alike enjoy boating through or strolling along the beautiful water. There are also a handful of top-notch restaurants and bars along the river.

River North boasts a handful of iconic buildings known for their history and jaw-dropping architecture. Merchandise Mart, The Wrigley Building, and the Holy Name Cathedral are all sites to behold.

Many people also appreciate the fantastic views that many of the River North skyscrapers offer. There’s nothing like sipping on your favorite drink and soaking up the ariel views of the Windy City.

Where to Live in River North and Old Town

If you’re interested in making one of the prettiest neighborhoods in Chicago home, consider securing an apartment in Old Town or River North. Check out a few of our favorite luxury buildings in each neighborhood.

Old Town Apartment Buildings:

River North Apartment Buildings:

To take the next step in making one of these apartments home, connect with an experienced broker today.

Still searching for the right neighborhood fit? Follow the link below!

Chicago Neighborhood Guide

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