Click on the numbers to view on the map.
1
the Obamas’ House5046 S. Greenwood Ave.
It may be Chicago’s best-guarded house without permanent residents. The good news: Concrete barriers have been partially removed and you can now walk (but not drive) on this public street (though not on the sidewalk), right in front of the Georgian Revival mansion the Obamas bought in 2005. It’s a secret how often the former first family stays here, but it’s often enough that the tree out front has been cicada-proofed.
2
THE Obamas’ First-Kiss RockCorner of 53rd Street and Dorchester Avenue
No one knows what powers this spot holds, but the Obamas’ first-date lip embrace, in 1989, must have been special to earn a plaque, attached to a boulder in front of this strip mall. The Baskin-Robbins where Barack treated Michelle to ice cream has been replaced by a Subway, but the mall now has another one in a different spot.
3
Former Holy Rosary Church Rectory351 E. 113th St.
Though no signs announce it, Obama’s first office for his first Chicago job, as a community organizer in the mid-’80s, was here in Roseland, on the first floor of the rectory behind a former Catholic church, now Greater Tabernacle Cathedral.
4
Hyde Park Hair Salon5234 S. Blackstone Ave.
Obama got his hair cut here weekly when campaigning. The staff realized he was a big deal when onlookers started showing up out front. Zariff, Obama’s barber, still works at the shop. Though the barbers say Barack was just another regular, his chair, signed and encased in bulletproof glass near the door, suggests otherwise. When the old patron occasionally shows up, the discussion is mostly about who has the most gray.
5
Valois Restaurant1518 E. 53rd St.
At this Hyde Park cafeteria, the eggs, sausage, and hash browns remain part of 44’s legacy. Will they taste better if you order them from the six combinations offered on the “President Obama’s Favorites” menu? Maybe. Obama hasn’t set foot here in years, but legend says his usual of egg whites, turkey sausage, toast, and hash browns is sometimes delivered to a car with tinted windows.
6
57th Street Books1301 E. 57th St.
The story goes that when Barack taught at the University of Chicago Law School, he’d stop in this shop every Sunday to browse quietly. Michelle picked out children’s books for their daughters here. And both Obamas later did book signings at the store.
