Michelle Obama’s Chicago: Self-Guided Routes
By Allison Yates
Readers & runners pose in front of Boxville, where along with Da Book Joint, Fleet Feet, On, and RNWY, we hosted our Book Club Run of Becoming.
Happy Obama Day! That may not be what this day is called officially, but Chicagoans are thrilled to celebrate the official launch of the Obama Presidential Center and the Obama Presidential Center Branch of the Chicago Public Library.
One of Read & Run Chicago’s most beloved events is our Running Tour of Becoming. At this event—first hosted in 2024 to celebrate the launch of On’s newest shoe, the Cloudmonster Hyper—we bring Michelle Obama’s memoir to life through movement in Hyde Park, the South Side Chicago neighborhood where Michelle spent several of her adult years prior to becoming First Lady.
“I’ve learned it’s okay to recognize that self-worth comes wrapped in vulnerability, and that what we share as humans on this earth is the impulse to strive for better, always and no matter what.”
In Becoming, readers get to experience Michelle’s story through her eyes: her years at a little girl under the nurturing care of her parents, heading off to Yale and discovering her community. Then, back to Chicago to build her career and meet former president Barack Obama, and finally, her experience living in the White House.
Naturally, many of those moments happen outside of Hyde Park, where our events take place. There are so many wonderful locations throughout the city that Michelle Obama mentions in her memoir, including Roseland, where Michelle watched Barack inspire community action, and the South Shore Cultural Center, where the pair wed in 1992.
Read & Run Chicago guide Fernanda leading a route in 2024.
But sadly, we can’t visit all of these locations in one event! The running routes on Read & Run Chicago’s signature events are typically three to five miles total, and Michelle Obama’s Chicago footsteps spans distance much greater than this.
We crafted three additional self-guided routes of varying lengths for the readers & runners who can’t get enough of Michelle’s story!
BONUS: Treat yourself after the run. Here are three eateries Michelle Obama loves and/or played a role in her story:
Baskin-Robbins, Garrett’s Popcorn, Italian Fiesta.
Route 1: South Shore Childhood Years
Readers & runners at a field trip to Michelle Obama’s childhood home.
Route Link | Mileage: 4.1 | Highlights: Michelle’s Childhood Home, Rosenblum Park, Bouchet Elementary (former Bryn Mawr Elementary), and Rainbow Beach
From the home she grew up in and the park where Michelle and Craig played, to the elementary school where she first gained her sense of self, the Lake Michigan beach she’d ride her bike to and the church her family attended, here is a classic early years route to bring to life the many stories Michelle shares in her memoir.
Read & Run Chicago’s 2025 event.
Note: Michelle attended Whitney Young Magnet High School on the Near West Side. It’s a bit far for this suggested route, but would make a great (and long) long run!
Route 2: The Hyde Park Adult Years
Readers & runners at Promontory Point during an event in 2025.
Route Link | Mileage: 3.1 | Highlights: University of Chicago, Promontory Point, The Obama Kissing Rock
From the Lakefront Trail to the University of Chicago and beyond, this route gives you the greatest hits of Michelle’s adult years.
The lakefront is a special place for all Chicagoans for many reasons—and for Michelle, it hold significance from both personal and professional life. As a child, Michelle and Craig and their parents would spend time on the weekends by the lake (her dad would drive them in his special Buick!), and while Michelle and Barack were dating, they would often spend time walking by the lake.
As they’ve continued their lives, the lake still holds the opportunity for family: Malia and Sasha were often brought there to have fun and temporarily relieve some campaign stress.
Read & Run Chicago guide Fernanda also reminded readers & runners of one of the most awe-inducing moments of the memoir. In 2008, after Barack Obama won the presidential election, they drove on an empty Lakeshore Drive to Grant Park, where an estimated crowd of 240,000 people waited to hear him speak. Fernanda recalls being amongst the attendees and feeling the silence and wonder in the crowd. She prompts readers & runners to remember a similar moment: “Think of a moment that made you feel goosebumps and gave you so much happiness for being there,” she urges us. The answers among the group as we run to our next stop are always wonderful.
Route 3: A Long Run of Major Life Moments
Barack Obama in Grant Park after winning the presidency in 2008. Photo Credit: New York Times
Route Link | Mileage: 11.6 Point-to-Point / 20.1 round trip | Highlights: South Shore Cultural Center, Obama Presidential Center, Grant Park, Sidley Austin (formerly Sidley & Austin)
This is a long run—literally! You can choose to do this as a 11.6 point-to-point run (and take public transportation or Divvy back to the start), or go big with a 20.1 round trip long run. This route takes you along our treasured Lakefront Trail from South Shore Cultural Center where Barack and Michelle said “I do” in 1992, to the law firm where they met and Grant Park, where over 240,000 Chicagoans heard Barack’s acceptance speech in 2008.
Michelle and Barack on their wedding day in 2002. Credit: Michelle Obama’s Instagram.