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Hyde Park, Illinois, United States

President Obama's Neighborhood

First family sites in Hyde Park, Kenwood and South Shore

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Difficulty: Easy
Length: 8.9 miles / 14.3 km
Family Friendly • Dog Friendly
 
Overview: Chicago is the adopted hometown of President Barack Obama, who gained his political bona fides, started his family and launched himself into the White House from the South Side. There are a smattering of Obama-related sites in other areas of the city—the North Side is home to some of his favorite restaurants, government buildings are downtown and he delivered his 2008 election night victory speech at the south end of Grant Park. But the area that contains the University of Chicago on the South Side is where you will get a feel for who he was and how he lived before moving to the White House.

Tips: Avoid visiting when the president is ensconced in the “Western White House” in Chicago. He rarely makes it home to Chicago, but when he does, the area goes on lockdown and it becomes difficult to maneuver around Secret Service detours.

Wear comfortable walking shoes and bring a jacket and umbrella. Chicago weather can be unpredictable.

Getting there: It's best to drive this tour if possible. Take Lake Shore Drive and exit at 47th Street. (On your right immediately after you exit is a small strip mall with a carryout pizza restaurant called Italian Fiesta Pizzeria. President Obama’s favorite sausage pizza is sold there.) There are plenty of places to park your car to walk portions of the tour.

If you prefer to take public transit, the Metra Electric makes two stops in Hyde Park—one serves 51st-53rd streets and the other serves 55th-57th streets. The area also is served by a number of CTA bus routes, including routes 1, 2, 6, X28, 10 and 55. Please note: The CTA has a tendency to change routes, schedules and even eliminate bus routes on a moment’s notice. Visit www.transitchicago.com for the latest information on routes, schedules and recommendations for the most efficient way to get to where you are going.

If you're walking, you'll probably want to forego the final two stops—the Jackson Park basketball courts and South Shore Cultural Center.

Points of Interest

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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 to buying this house, the Obamas lived in a vintage condo at 5450 S. East View Ave.)

The home purchase took on political significance for its connection with Tony Rezko, a Chicago real estate developer who was one of Obama's earliest supporters. The longtime political fundraiser was later convicted on several counts of fraud and bribery.

The previous owner wanted to sell the house and a neighboring empty lot in one deal. On the day the Obamas bought the mansion, Rezko's wife, Rita, bought the adjoining empty lot. Obama has acknowledged he told Rezko about the need to close both deals on the same day, but has denied the two coordinated to make the purchases.

In 2006, the Obamas bought a 10-foot strip of the empty lot from Rezko for $104,500. Rezko never developed the remaining portion of the corner lot.

Once, when Sen. Obama called the mansion to brag to his wife about federal legislation he helped pass, Michelle Obama ignored him, saying, “We have ants.” She wanted him to stop on his way home to pick up some traps for the manse.

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Obama Family Home
5046 S. Greenwood Ave.
Northwest corner, East Hyde Park Boulevard and Greenwood Avenue
Chicago
Shopping
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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 summer job at Sidley & Austin, a law firm in Chicago. A year earlier I had been working as a community organizer in some of Chicago's poorest neighborhoods, and I struggled with the decision to go to a large firm. But with student loans mounting, the three months of salary they offered wasn't something I could pass up.

"Michelle worked at Sidley, too, and, in the luckiest break of my life, was assigned to be my adviser, charged with helping me learn the ropes. I remember being struck by how tall and beautiful she was. She, I have since learned, was pleasantly surprised to see that my nose and ears weren't quite as enormous as they looked in the photo I'd submitted for the firm directory.

"Over the next several weeks, we saw a lot of each other at work. She was kind enough to take me to a few parties, and never once commented on my mismatched and decidedly unstylish wardrobe.

"I asked her out. She refused. I kept asking. She kept refusing.

" 'I'm your adviser,' she said. 'It's not appropriate.' Finally, I offered to quit my job, and at last she relented. On our first date, I treated her to the finest ice cream Baskin-Robbins had to offer, our dinner table doubling as the curb. I kissed her, and it tasted like chocolate.

"I had known those student loans were going to get me a great education, but I had no idea they'd get me my first date with the love of my life."

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1400 E. 53rd St.
Chicago
Viewpoint
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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 Muhammad Ali). By the time the shop moved to the Blackstone address a block away in 2007, the barber came to him.
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Hyde Park Hair Salon
5234 S. Blackstone St.
Chicago
Shopping
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Valois Restaurant

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 the food and ordering anything that looks yummy. Expect to spend less than $10 per person for a hearty (though not necessarily heart-healthful) meal. And please note: Valois accepts U.S. dollars only, no credit cards.

Expect to see plenty of police officers and University of Chicago students loading up on the good, cheap grub.

Valois
1518 E. 53rd St.
Chicago
773-667-0647

Hours: Daily 5:30am-10pm
Campground
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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.

Passers-by at the front of the building can get a good look at his former windows on the first floor, just to the left as you look at the doorway.

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Obama's apartment
5429 S. Harper, Unit 1 North
Chicago
Shopping
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Medici

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.

Inside the other entrance is an old-fashioned bakery, where the croissants are notable among a number of other sweets to accompany your coffee.

This neighborhood mainstay started as an art and coffee house. It still serves great coffee, but it doesn't serve alcohol. So if you want wine with dinner, bring your own.
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Medici
1327 E. 57th St.
Chicago
773-667-7394

Hours: Monday-Thursday 7am-11pm
Friday 7am-midnight
Saturday 9am-midnight
Sunday 9am-11pm
Viewpoint
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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 cookbooks. It also sells the president's two books, “Dreams from My Father” and "The Audacity of Hope.”

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57th Street Books
1301 East 57th St.
Chicago
773-684-1300

Hours: Daily 10am-8pm
Hotel
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University of Chicago Lab School

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 by University of Chicago Professor John Dewey to test his educational theories. The school employs an unregimented but demanding curriculum that focuses on teaching students to analyze and critically solve problems, rather than simply absorb facts.

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University of Chicago Lab School
1359 E. 59th St.
Chicago
Building
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The University of Chicago Law School

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 if the door is locked or a class is in session, there is a window in the door to view the room.

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University of Chicago Law School
1111 E. 60th St.
Chicago
Viewpoint
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Jackson Park Basketball Courts

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 story as it was reported in an issue of Esquire magazine:

"When I played basketball with Barack, he was quietly confident, which means he had good self-esteem without being cocky," Robinson said. "He was certainly a team player—he wasn't a pig, he passed when he was supposed to pass, and he cut when he was supposed to cut. To me, that speaks to a lack of selfishness. He had natural leadership ability, because he didn't just pass me the ball because he was dating my sister. Whenever a player gets tired, he reverts back to the player he truly is. That's how you tell. And we played for hours. That's how I could tell."
Building
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South Shore Cultural Center

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 from its beginnings as an exclusive country club that excluded Jews and other minorities, including African-Americans.

The Mediterranean Revival-style building was built in 1916 as a playground for Chicago's wealthiest citizens. It was designed by architects Marshall and Fox, who later designed many of Chicago's most luxurious hotel and apartment buildings, including the Drake Hotel.

Membership in the country club peaked in the late 1950s and began to fall as African-Americans began settling in the surrounding South Shore neighborhood. Black members were not allowed to join the club, which went out of business in the 1970s.

The Chicago Park District bought the property in 1974 and planned to demolish the severely deteriorated clubhouse. Community members rallied together to save the historic building.

To get back to the city center from the South Shore Cultural Center, head over to the Metra Electric train station across the street from the cultural center. Trains stop on a regular basis.

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South Shore Cultural Center
7059 S. South Shore Drive
Chicago
773-256-0149
Campground
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Kam Isaiah Israel Congregation

Across Greenwood Avenue to the east, the Byzantine structure is the KAM Isaiah Israel Temple, an architectural landmark designed by Alfred Alschuler in 1924.
Campground
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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.
Pictures in this guide taken by: tollibaa, CindyRichards, krbose

President Obama's Neighborhood Map


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About the Author

BonnieMcGrath
BonnieMcGrath
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Bonnie McGrath is a lawyer and journalist in Chicago. Her blog, "Mom, I think I'm Poignant," is on ChicagoNow.com

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