February 10, 2021

Chicago is a city unlike any other — with an incredible history to match! You can find a story around just about every corner of this town. And our senior clients often love not only talking with us about their connections to Chicago’s storied past, but going out and visiting historic spots for themselves! 

Finding Classic Chicago in 2021

Whether you’re feeling nostalgic for old school Chicago, or want to learn a little bit of our local history for yourself, here are some of the best ways to discover classic Chicago in 2021.

Retro Eats

Can a bite of food transport you back in time? It can in Chicago! Our area is home to restaurants that are legendary for starting food crazes that have swept the nation; others have been continuously operating since the 1800s! 

Some of the area’s most famous retro eateries include Orange Garden Chinese, Manny’s Cafeteria & Delicatessen, The Berghoff, and Daley’s Restaurant. Eat like a Beatle at Margie’s Candies, or satisfy your sweet tooth with a retro dessert from Dinkel’s Bakery or the Original Rainbow Cone. Revisit a Chicago classic by getting an Italian Beef from Al’s, or deep dish from the original Uno’s or a vintage Lou Malnati’s. 

To find options for delivery and takeout during COVID-19, check out our online guide!

Historic Spots

Chicago is a time capsule in a lot of ways. As much as things change, others stay the same. To get swept up in the history that makes our area so unique, look for local sightseeing tours. There are lots of options — from bus tours that whisk you back to the days of Al Capone, to riverboat cruises that shine the spotlight on our area’s amazing architecture. 

Look for incredible architecture in Oak Park, home to the highest concentration of Frank Lloyd Wright buildings anywhere in the world (plus the original birth home of Ernest Hemingway). See the stunning Pullman Park National Monument, or stroll the Midway Plaisance, once home to the World’s Columbian Exposition in 1893. Check out some of the vintage houses tucked in downtown along the Gold Coast or Millionaire’s Row, or go looking for history in one of Chicagoland’s oldest suburbs.

For easy ideas on how to make day trips easier and safer for the elderly, click here!

Musical Destinations

Music can help bring up old memories and get you moving. Take a walk down memory lane by sampling the classic tunes at Buddy Guy’s Legends, B.L.U.E.S., Kingston Mines, or the Green Mill Cocktail Lounge. Enjoy an outdoor show at Ravinia Park or Northerly Island.

For more ideas on using art and music to connect with the elderly while staying home during COVID-19, click here!


When you want to learn more about the unique history that has shaped Chicagoland, turn to one of our area’s incredible museums! 

You’ll find lots of informative and dynamic exhibits at the Chicago History Museum. The Museum of Science and Industry and the Art Institute of Chicago also have plenty of local exhibits and artifacts. Pay a visit to the oldest home in Chicago at the Clarke House Museum, or do a little research into your neighborhood at the Newberry Library or Chicago Cultural Center. 

Click here for 10 more fun ways to help active seniors enjoy Chicagoland. 

For more ways to enjoy these museums from the comfort and safety of home during COVID-19, visit this great guide from Choose Chicago.

Vintage Stores

Looking to bring a little history home with you? Chicago is full of fantastic antique and vintage stores. 

The Vintage Garage takes over several floors of an Uptown parking garage with retro goodness each fall. Find one-of-a-kind clothes at Shangri-La Vintage, Viva Vintage, or Elliott Consignment. Pick up antique furnishings at Antique Resources, the Broadway Antique Market, Vintage Quest, or Dial M for Modern. Grab a family member’s favorite record at Dave’s, Laurie’s Planet of Sound, or Bob’s Blues and Jazz Mart. 

For more reasons why we love the Windy City, click here!

Ready to Help the Senior In Your Life Really Enjoy Chicago? Companions for Seniors Is Here to Help

Curious about other ways to help your senior loved one remain active and social, while aging in place? Looking for caregiving and companionship services in the Chicagoland area? If you have any questions about caring for the older adult in your life, don’t hesitate to reach out to Companions for Seniors! 

We’d be happy to be your sounding board, share our experiences, and talk over any questions or concerns you may have about any aspect of providing care for your aging loved ones.

Don’t hesitate to give us a call at 866-910-9020, or fill out our online contact form to learn more today!