Chicago has a certain magnetism in early summer—as Barack and Michelle Obama, who met in the Windy City as young lawyers, discovered in the ‘80s. It was here that Barack dated and married Michelle, worked as a local community organizer, and then taught at the University of Chicago law school before running for U.S. Senate. And it is here that the $800 million Obama Presidential Center will open June 19, on the Juneteenth holiday, not far from the University of Chicago campus.
The opening comes at an ideal time for the city: The blizzards are long gone, the humidity has yet to fully arrive, and the beaches and parks along Lake Michigan fill with loungers. If you want to follow in the former president’s footsteps, visit some of his most formative and cherished sites around the city on this Obama-themed itinerary of Chicago.
Start your day at Valois Restaurant
1518 E. 53rd St. | View on Google Maps
Valois Restaurant is one of the oldest cafeteria-style restaurants in the U.S., where a young Barack Obama often got his fill.
Photo by Kathleen Hinkel
Obama frequented this cafeteria-style restaurant when he lived in a nearby studio apartment in his 20s, working as a community organizer. A few blocks from the University of Chicago, Valois is festooned with murals of Chicago landmarks like Washington Park and the Field Museum. The 105-year-old Hyde Park fixture is famous for all-day breakfasts: a stack of pancakes topped with strawberries, giant omelets that take up the entire plate, and—reportedly one of the former president’s favorites—a platter of egg whites, hash browns, turkey sausage, and wheat toast, with hot tea.
Bask in butterflies at the South Shore Cultural Center Park
7059 S. South Shore Drive | View on Google Maps
During their wedding reception on October 3, 1992, the Obamas danced “almost all night,” as Michelle wrote on Instagram, at this 71-acre park. (The first dance was Stevie Wonder’s “You and I,” according to Brides magazine.) Once a segregated country club that excluded Black and Jewish people, the city-owned park invites all visitors today to its nature sanctuary, butterfly garden, public beach area, and the R&B-focused South Shore Summer Festival every August.
Be inspired at the Obama Presidential Center
6001 S. Stony Island Ave. | View on Google Maps
The Obama Presidential Center is a magnificent display of architecture and design.
Renderings courtesy of The Obama Presidential Center Campus
Opening on Juneteenth, the Obama Presidential Center was designed to be a “hub for change,” as Obama called it. In addition to displaying films and photos of organizers and volunteers who worked on the former president’s 2008 campaign, the center will offer educational training for teachers and college students as well as programs like Teen Action Lab, which uses sports to train kids on health and wellness issues. The center sits on a 19-acre plot in cherry-blossom-packed Jackson Park, near the Griffin Museum of Science and Industry, and is predicted to see 700,000 annual visitors. The campus will include a museum (containing memorabilia from Obama’s presidency); a restaurant run by Cliff Rome, owner of Peach’s in the nearby Bronzeville neighborhood; and a “sky room” overlooking the city’s South and West Sides.
Grab a quick lunch at One Prudential Plaza
130 E. Randolph St. | View on Google Maps
Known as “the Pru,” this skyscraper overlooking Millennium Park along the Magnificent Mile was the site of Obama’s campaign headquarters in 2012. Three months before the election, the president visited his campaign staff here by way of helicopter and underground motorcade. The offices are mostly closed to the public, but visitors can dine at restaurants on the first floor, where the former president likely got his lunches during the campaign. Head to Giordano’s for Chicago-style deep-dish pizza, or order the chocolate-chip banana option at Wildberry Pancakes and Cafe.
Admire great works at the Art Institute of Chicago
111 S. Michigan Ave. | View on Google Maps
In the city’s downtown Loop area, the Art Institute of Chicago has several types of art, including ancient, Impressionist, and contemporary.
Photo by ChicagoPhotographer/Shutterstock
When the Obamas talked about dating and their relationship in a 2019 interview with Today, Barack advised, “Guys out there, art impresses people.” The Art Institute of Chicago certainly wows visitors with its stately bronze lions flanking the entrance steps and works by Van Gogh, Picasso, Georgia O’Keeffe, Chicagoan Simone Leigh, and Edra Soto. Barack and Michelle spent their first date here in 1989 and dined at the on-site café. While their order is lost to history, today’s menu includes a chicken flatbread with chili crisp and hot honey, an herb-butter pot pie, and a strawberry matcha cheesecake parfait.
Dine on Mexican salsas and cactus sorbet at Topolobampo
445 N. Clark St. | View on Google Maps
Many of the Obamas’ early date-night restaurants in Chicago no longer exist. Longtime North Side fixture Gordon closed in 1999, where Barack proposed to Michelle by instructing a waiter to bring an engagement ring with dessert. But Topolobampo, a favorite of Barack and Michelle’s a few blocks from the Gordon site, is still dishing out high-end Mexican food. The one-Michelin-star restaurant is run by top Chicago chef Rick Bayless, who once called the Obamas “adventurous eaters.” The restaurant locally known as “Topolo” serves dishes such as wood-grilled Spanish octopus with cascabel and sunflower seed salsa and lime-tamal pudding cake with pitaya sorbet.
