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Top Activities for Older Adults in Chicago



“This is my kind of town, Chicago is,” crooned Frank Sinatra. Even with the Yoda-like grammar, one can appreciate the sentiment. Though the Windy City – so named for its 19th-century politicians’ proclivity toward spewing “hot air'' - can actually get pretty windy, the happy throngs of active adults lucky enough to retire in Chicago wholeheartedly agree with Old Blue Eyes.

As the cultural hub of the Midwest, Chicago perfectly merges the down-to-earth with the trendy and sophisticated. It excels in, well…pretty much every category. From stunning lake views and green spaces to jaw-dropping architecture, world-class museums, music, food, and sports teams, Chicago is a city of superlatives.

The list of adult activities in Chicago is endless. All you need is a good pair of sneakers and unlimited enthusiasm. Here are a few suggestions to get your Chicago adventure started.

Skydeck Chicago at Willis Tower

On a clear day from Skydeck Chicago you can see panoramic views that extend into Indiana, Michigan, Iowa, and Wisconsin. The Willis Tower is no longer the tallest building in the world but once you step out onto The Ledge, an enclosed glass balcony that extends four feet out over the city, you’ll agree it is still definitely high enough.

Chicago River Tours

The Chicago River, the only river in the world that flows permanently backward, offers great opportunities for cruising, kayaking, or canoeing through the heart of the city. The river flows past some of the city’s most notable architecture including the Willis Tower, the Wrigley Building, and Navy Pier.

Navy Pier

Grab a friend, or the grandkids and head over to Navy Pier, one of Chicago’s highlights. Jutting into the waters of Lake Michigan, the 3,300-foot pier features almost 50 acres of exhibits, rides, and parks.

Magnificent Mile

The Magnificent Mile is where fashion, architecture, and history intersect. As you walk from the Chicago River to Oak Street, you’ll pass iconic landmarks and plenty of high-end shopping opportunities.

Chicago Cultural Center

Originally built as Chicago’s first public library, The Chicago Cultural Center is now doing double duty as a renowned architectural monument and event venue. This popular Chicago mainstay features more than 1000 free concerts, films, art exhibits, and other cultural events every year.

Wrigley Field

You don’t have to be a diehard baseball fan for Wrigley Field to be a bucket list destination. Built in 1914, it is the oldest baseball venue in the National League. When it comes to fun things to do for seniors in Chicago, look no further.

Art Institute of Chicago

Located in Grant Park, along with the Museum Campus and Millennium Park, the Art Institute of Chicago is one of Chicago’s most visited attractions. The museum showcases 300,000 works of art from masters of the past and present. Once you’ve gotten your fill of artistic excellence, take a stroll through Grant Park, the city’s primary park in the downtown Loop.

Northerly Island

Northerly Island was originally the vision of 1893 World’s Fair architect Daniel H. Burnham. Today the island reflects the parks, harbors, trails, beaches, and wide-open green spaces he envisioned. Pack a picnic and spend a day experiencing nature, convenient to the city.

Chicago for seniors is like baseball at Wrigley Field, an invigorating, exciting, unrivaled experience. Check out Overture Yorktown, Overture’s premier active adult community in Chicago, and prepare to knock this active adult chapter out of the park.