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President Obama's Neighborhood

First family sites in Hyde Park, Kenwood and South Shore
Rating: 5 out of 5 by EveryTrail members
Difficulty: Easy
Length: 8.9 miles
Duration: Unknown
Family Friendly

Overview :  Chicago is the adopted hometown of President Barack Obama, who gained his political bona fides, started his family and launched... more »

Tips:  Avoid visiting when the president is ensconced in the “Western White House” in Chicago. He rarely makes it home to Chicago, but when... more »

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Points of Interest

1. The Obama Family Home

Walk on the south side of East Hyde Park Boulevard. You can only see the house from that side due to Secret Service protection on the north side.

The Obamas were able to buy this renovated mansion in 2005 for $1.65 million after then Senator-Elect Obama signed book contracts with Crown Publishers and Alfred A. Knopf at the end of 2004. (Prior... More

2. The Obamas' First Date

A Subway sandwich shop is there now, but it used to be a Baskin-Robbins ice cream shop and it’s where the first couple had their first date—eating ice cream while sitting on the curb—in the summer of 1988.

Here's how Obama himself told the story on Oprah Winfrey's website:

"I met Michelle in 1988, after my first year of law school, when I took a... More

3. President Obama's Barber Shop

At the Hyde Park Hair Salon, you can see the chair President Obama sat in when he got his haircuts here. It’s under glass and the owners welcome gawkers.

Before his move to the White House, President Obama visited the original storefront barbershop at 1464 E. 53rd St. on a regular basis (as did other neighborhood celebrities such as boxer... More

Valois is a neighborhood establishment for the talking of politics and President Obama’s favorite cafeteria.

The sign outside tells you everything you need to know: See Your Food. That means the food is displayed along a smorgasbord. Rather than sitting down and giving your order to a waiter, you grab a tray and walk along the line, looking at... More

5. Barack Obama's Single Apartment

Obama lived alone in this rental apartment before he was married.

Sources—including Obama himself—vary as to the exact years the president lived in apartment 1N as a young, single and college-educated man with big dreams for the future. He most certainly spent a significant amount of time in this vintage character-laden court building.

... More

If you didn't eat your fill at Valois, stop in here and order a Cheddar cheeseburger served medium, just the way the president eats it.

Medici is divided into two spaces with different entrances. On the “Cheddar cheeseburger” side, the menu has great sandwiches, soups, salads, chili and many other things served in a dark, cozy atmosphere.

... More

7. 57th Street Books

The Obama family's favorite bookstore is in an ancient cellar. The president did his book signings in the shop. He's a good customer there as well.

There are pictures and the staff will tell you interesting stories.

The cooperative, member-owned bookstore was founded in 1983. It's known for its selection of mystery, science fiction and... More

Before they moved to Washington, D.C., and enrolled in the prestigious Sidwell Friends School there, first daughters Malia and Sasha attended school at the prestigious University of Chicago Lab School here.

This internationally renowned school serves children in kindergarten through 12th grade who "learn by doing." The school was founded in 1896 ... More

The president taught constitutional law at the University of Chicago from 1992 to 2004. Classroom V is in a building designed by noted architect Eero Saarinen in 1956.

Enter, turn left and walk toward the right corner of the hall. You will see information on the wall outside the classroom about Obama’s tenure as a lecturer inside the room. Even... More

If you have time and energy, go south around the Museum of Science and Industry (site of the 1893 World’s Fair) at the eastern tip of Hyde Park and south through Jackson Park. The basketball courts you see are the ones on which Michelle Robinson’s brother, Craig, tested Barack’s character and reported him to be a good guy. Here's the often-told... More

After exiting Jackson Park, go a tad farther south to the former South Shore Country Club that now serves as a Chicago Park District facility. It is here that the first couple held their wedding reception in 1992.

The South Shore Cultural Center sits on a 65-acre park with a golf course, tennis courts and bathing beach open to everyone—a far cry ... More

Across Greenwood Avenue to the east, the Byzantine structure is the KAM Isaiah Israel Temple, an architectural landmark designed by Alfred Alschuler in 1924.

13. President's Health Club and Press' coffee shop

If you begin your walk down East Hyde Park Boulevard at the Metra Station, turn east and look at the glassy high-rise buildings just to the north. The president works out in the buildings’ health club when he is home. The press waits in a coffee shop next to the Hyde Park Art Center at 5020 S. Cornell in back of the building.