It’s time to take another trip through one of Chicago’s 77 neighborhoods to explore some rich history, sites, and, of course, enjoy some delicious food. This time were going to a neighborhood many know as the Chicago home of the Obama family: Kenwood.

Things to do in KenwoodKenwood past and presentA tour of the Kenwood neighborhood: landmark homesLocal art and dining in Kenwood

Kenwood past and presentSettled in the 1850s by Dr. John Kennicott around present-day 48th Street and named after his ancestral family lands in Scotland, Kenwood has grown to be one of the most culturally diverse neighborhoods in all of the city.

Kenwood is the story of Chicago’s greatness in its purest form. And I’m not just saying this because my grandma lives nearby, or because I spent a considerable amount of time there in my childhood with friends. I’m saying this because it’s undeniably true.

Now, with the Obama Presidential Center opening nearby in Jackson Park, thousands of visitors will be making their way to this part of Chicago. While many will come for President Barack Obama’s legacy, they’ll quickly discover that Kenwood has stories, landmarks, and flavors to sustain their visit for weeks on end. The history of this neighborhood is deep and rich, which explains why the Obamas found it worthwhile to settle there.

A tour of the Kenwood neighborhood: landmark homes

Frank Lloyd Wright’s Heller House near Kenwood

A historic home in the Kenwood neighborhood; photo by Adam Alexander Obama homeOkay, on our first stop, is the most famous address in the neighborhood on 50th and Greenwood Avenue (5046 S. Greenwood Ave.).

Though they no longer live there full-time, the Obama family home remains one of Kenwood’s most recognizable landmarks. It serves as a reminder that a young community organizer who once walked these streets would eventually become the 44th President of the United States.

Please note, this is still a private residence. We’ll just admire it from a distance and wave at the Secret Service as we go to our next stop.

Muhammad Ali house, photo by Adam AlexanderMuhammad Ali homeAlright, let’s keep going and head one block north to 4944 S. Woodlawn Ave to visit the greatest of all-time. No, I’m not talking about Michael Jordan (this time). I’m talking about the other G.O.A.T. None other than Muhammad Ali (4944 S. Woodlawn Ave.).

Ali purchased this sprawling home in the 1960s and would go on to live in Chicago on and off for more than a decade. Ali’s career was just as grand as his home. I imagine he found great solace resting here after his various championship bouts throughout the late 60s and 70s.

Muddy Waters homeOver the years, you might have noticed that President Obama often shared a summer playlist of songs he was listening to. Well, one legendary artist worth adding to that list, who also called Kenwood home was none other than a man referred to as the “Father of Modern Chicago Blues,” Muddy Waters.

Let’s head north to 4339 S. Lake Park Avenue to check it out. Waters helped transform American music and influenced everyone from The Rolling Stones to Jimi Hendrix.

Standing near his former residence, it’s hard not to imagine the sounds that once flowed through the neighborhood and eventually around the world. If you’re looking for a song recommendation, be sure to check out, Got My Mojo Working as you read the sign in front of his home. I can’t wait until his home is fully transformed into a museum. Let’s be sure to come back when it opens!

Local art and dining in Kenwood

Carver 47 inside Little Black Pearl ChicagoLittle Black Pearl Art Design CenterIf youre looking for creativity in action, we’ll have to stop by Little Black Pearl Art Design Center. For decades, this community arts organization has provided opportunities for young people to develop artistic skills while preserving and celebrating Black culture. From exhibitions to educational programs, it remains one of the South Side’s most important cultural institutions. And aesthetically, its one of the most beautiful places I’ve had the pleasure of visiting in Chicago. True story. No cap.

Norman’s BistroAre you hungry yet? We’ve been out exploring for a while, so I’m going to assume that you are, because I am. Let’s make our way to Normans Bistro.

This neighborhood restaurant blends Southern comfort food with Caribbean influences. The food is as memorable as the atmosphere. What do I recommend? Everything. But today I’m in the mood for some of their chicken gumbo, so let’s go with that. Oh, and if you stop by on Sunday you’ll be able to enjoy live jazz with your meal, so take note of that!

I’ve been told that its a great idea to walk after your meals, so let’s keep the car parked and walk the neighborhood to enjoy the scenery. If not for nothing, this will help us avoid falling asleep after such a scrumptious and satiating meal.

Kenwood’s legacyAs you’ve seen throughout the day, one of Kenwood’s greatest strengths is its architecture. Yes, visiting homes where icons once lived in Kenwood is necessary, but what truly makes Kenwood special is the everyday Chicagoans who have all left their mark.

And as we take this walk, we’ll be reminded of just that, because even though we can’t name every person who resides in the beautiful homes and neighborhoods we pass, we can be certain that they have made an indelible impact on Kenwood, and all of Chicago. It’s a place where Black history, immigrant history, political history, and cultural history intersect in ways that feel uniquely Chicago.

So yes, come to the South Side for the Obama Presidential Center, but stay long enough to discover the Muddy Waters connection, the Muhammad Ali history, the artistic spirit and aesthetics of Little Black Pearl, and a meal at Norman’s that you’ll be thinking about on the drive home.

Have you ever visited any of these cultural institutions in Kenwood? Did I miss anything? Let me know, so I can check it out on my next drive.