Obama’s Chicago: Seven Sites in the City

Visit historical locations and personal favorites of the 44th president in his hometown of Chicago.


On November 4, 2008, the people of the United States elected Barack Obama as their 44th president. In Chicago, a sea of smiling faces and an unseasonably warm evening greeted him as he strode to the stage in Grant Park. “If there is anyone out there who still doubts that America is a place where all things are possible,” he said, “who still wonders if the dream of our founders is alive in our time; who still questions the power of our democracy, tonight is your answer.”

The path to find this answer stretched from Hawaii to Indonesia to New York, eventually bringing Barack Obama to Chicago as a community organizer, a professor, a state senator, a U.S. senator and ultimately president. Through it all, Chicago became his home and remains so, even as he takes up residence in the White House.

Given the abundance of interest in all-things Obama, from souvenir dishware to T-shirts, important Chicago destinations on his path to the presidency have drawn travelers from across the globe (sorry, Al Capone and Michael Jordan, it’s Obama’s Chicago now). Following are a few places to visit in Chicago—notable sites from his community organizing days on the South Side to his victorious election night celebration by the lake, to give you a sense of the presidential path through Chicago.

Gymnasium at Our Lady of the Gardens Catholic School

In the late 1980s a young Barack Obama, community organizer, held a meeting here for residents of Altgeld Gardens, a public housing project, to fight for the removal of asbestos from their homes. The foundation for his successful campaign, motivating people to organize and bring the change they seek, began here. 13382 S. Langley Ave.

University of Chicago

Before becoming a politician, Professor Obama taught constitutional law at the University of Chicago from 1993 until 2003. Allegedly, his favorite room was Room V in the law school building; you’ll enjoy walking amidst the gothic architecture and quiet spaces of campus (as I’m sure he did). 1111 E. 60th St.

57th Street Books

For a respite, stop by 57th Street Books, one of the Obama family’s favorite bookstores. Buy a copy of Dreams from My Father (Three Rivers Press, 2004) or The Audacity of Hope (Crown, 2006). Author Obama held book signings here for his now best-selling works. 1301 E. 57th St., tel. 773-684-2804. Hours: Mon. through Fri. 10 a.m. to 9 p.m., Sat. and Sun. 10 a.m. to 8 p.m.

Obama Family Home

If the first family is here, you’ll get nowhere near their home in the Kenwood neighborhood. However, if they’re in Washington, you can get close enough to snap a photo of the residence the president still calls home. 5046 S. Greenwood Ave.

Hutchinson Field—Grant Park

A throng of people, hundreds of thousands strong, gathered here that historic November night to celebrate a new president. The stage was set up at the south end of the field, with the crowd stretching out toward the Loop. For a good perspective, find a tree on a slope near the middle of the park on the east side overlooking the field, the city behind you and the lake beyond, and imagine revelers filling the space in between (I have a personal affinity for this spot). 901 S. Columbus Drive.

National Campaign Headquarters and Transition Offices

You won’t be able to see much here, but take a walk by the buildings where the successful campaign and transition occurred. Campaign Headquarters were located at 233 N. Michigan Ave. on the 11th floor. Transition offices were in the Kluczynski Federal Building, 230 S. Dearborn St.


The restaurant of choice for President-elect and Mrs. Obama’s celebratory dinner following the election. A noted Obama family favorite, Spiaggia is considered one of the finest restaurants in the city. Finish off your Obama-Chicago tour with a meal here, and consider perhaps how you too can be the change you seek. For lighter fare (and lighter on the wallet), consider the Cafe Spiaggia. 980 N. Michigan Ave, tel. 312-280-2750. Hours: Sun. through Thurs. 6 to 9:30 p.m., Fri. and Sat. 5:30 to 10:30 p.m., Sun. 6 to 9 p.m. Reservations required. Reservations can also be made online at

Destinations: Chicago

Themes: Historical Vacations, Urban Endeavors

Activities: Sightseeing

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