The Obama’s Chicago - A Walking Tour of Hyde Park, Kenwood, and South Shore Neighborhoods (Illinois)
“Umm, are you really going to The Obama’s house?” asked the Lyft driver. I confirmed that was indeed my drop off location. I’d parked around the corner from there and it was the simplest destination to put in the app to get back to my car after this 6 mile walk I’d been on.
Apparently I’m not the only one that was (previous to this day) unaware that the location of the Obama family home, and other Obama-adjacent locations, are well documented.
I was in Chicago for work and I’ve been really feeling the itch to get out and explore parts of Chicago I normally don’t. It was a bit chilly and cloudy, so my biking and paddling ideas were out. I was perusing AllTrails when a walking tour of Hyde Park, Kenmoore, and South Shores neighborhood caught my eye. Double clicking in, the description referred to this as a walking tour of 'Obama's Chicago' and I was sold!
Honestly, the app didn't work well for navigating this, and was missing some spots, so I built out this Google Map you can use.
I might be biased, but I think spring was the absolute best time to be there. This is a neighborhood of mature trees and dense, beautiful landscaping in some parts. There were so many colorful blooms to enjoy! An even better time to go will be when the Barack Obama Presidential Center opens up in 2026 so you can add that experience on as well.
The Obama Family Home
KAM Isaiah Israel Temple
Across the street from the Obama home is a beautiful Byzantine-inspired synagogue. Designed by well-known Chicago architect Alfred Alschuler, it’s the oldest in Chicago.
The Kissing Rock
Definitely the cheesiest landmark along the way, but a sweet story. (badum tss) The Baskin Robbins is still there, too.
Barack’s Apartment
The most pedestrian stop on the list. Just a regular ole apartment building. But I suppose that’s the point.
57th Street Books
I was thrilled there was a bookstore on the list. I opened the door down in to the cellar and was greeted by a nice shopkeep. I spent way too much time in here for someone with only a mini backpack to put belongings in. But finally, I settled on this book and continued on.
Chicago Lab Schools
Affiliated with the University of Chicago, and more or less on its campus, the Obama’s daughters, Sasha and Malia, went to school. On the door I saw a sign that read “We value learning experientially, exhibiting kindness, and honoring diversity.”
University of Chicago Law School
I had never been to the University of Chicago or its Law School, but the reputation certainly precedes it. It was a beautiful and stately campus. Old buildings and new, with a massive greenspace stretching out between. It’s crazy to think how much time I’ve spent in Chicago only to have moments like this, where I see a new-to-me site and think WOW, I haven’t seen Chicago at all.
I spent a moment in front of the reflecting pond as law students passed by. The walking tour said you can go look at the classroom where Obama taught and that there is also a plaque outside the door if class is in session and you can’t go in. But I tried one set of doors and they wouldn’t open without a pass, so I chickened out and moved on, content with having seen the school.
I headed east towards the interstate, passing more campus buildings. A couple of which included public restaurants BarDavid and Truth Be Told A very different campus life than I knew! Soon campus was behind me.
Barack Obama Presidential Center
Renderings from Michael Van Valkenburgh Associates Inc. More about the center here.
Once I passed under the Chicago Skyway, my focus shifted to the construction in front of me and I realized the monstrosity ahead of me was the soon to be Barack Obama Presidential Center. It felt garish, yet as I looked closer, the stone that was being used was appealing. Looking it up later and seeing the renderings and the context of the park it will sit in, it hit different. I like the natural yet modern look the photos portray. So I suppose time will tell!
Due to the construction, I had no view of the park or ability to enter it, and had to walk city streets for a while. Kids were getting out of school and waiting for buses and I felt like I was sticking out like a sore thumb. It made me eager to get into the park.
Jackson Park / Basketball Courts
As the story goes, Michelle Obama's brother Craig played basketball with Barack during their early dating stages to assess his character (and athletic ability). This is where it went down, and he got the thumbs up.
I was guessing at which basketball courts in Jackson Park were ‘the courts’, and I think I guessed wrong. But I put the right ones on the map above.
I followed a disc golf course for a bit, then I passed a marina where some people were sailing. Another side of the city I’ve not seen.
South Shore / South Shore Cultural Center
I was thrilled to reach Lake Michigan and catch a glimpse of the Chicago skyline from this new perspective, though it was a pretty rough looking for a beach. It sounds like Burnham Park / Promontory Park, north of Jackson Park, is the place to go for a gram worthy photo. I followed a golf course for a bit, finally reaching the cultural center where the Obama’s wedding reception was.
I failed to grab a decent picture of the structure because I had to pee, my phone was dying rapidly, and I got distracted by a huge mushroom growing out through the bark of one tree.
I took advantage of a porta potty on one of the holes (surely looking like a supreme weirdo to the guys playing the hole), and ordered up a Lyft to take me back to my car. I had a really great convo with the driver on the way back. The type of interaction that feels as important to the experience as the walk or the sites.
Future Itineraries
Obama Presidential Center, Valois Restaurant (on the map, though I didn’t go there), Museum of Science and Industry, Osaka Garden, Burnham Park and Promonotory Point