More than twenty years before Barack Obama became the 44th President of the United States — and the first African-American to hold the office — he quit his job in New York, bought a used car, and drove to Chicago.

In his memoir, Dreams from My Father, Obama describes his first days in the city: driving up Martin Luther King Jr. Drive and down Cottage Grove Avenue, through Chatham and Bronzeville — seeing echoes of the Great Migration of the 1920s, imagining novelist Richard Wright and jazz greats Duke Ellington and Ella Fitzgerald walking those streets. He eventually alighted at Smitty's Barber Shop in Hyde Park, where he got a $10 haircut and a free Chicago history lesson.

Smitty said, "The night Harold won, let me tell you, people just ran the streets. It was like the day Joe Louis knocked out Schmeling. Same feeling. People weren't just proud of Harold. They were proud of themselves."

It was 1985, and the city that invented plantation politics, only recently described as the most segregated in America, had just done the unthinkable: it had elected a black mayor, Harold Washington. Change was in the air. Obama took a job as a community organizer in the Far Southeast Side neighborhoods of West Pullman and Roseland, which had been hit hard by factory closures, and worn down by years of neglect by the city government. His work involved building partnerships and securing funding for job-training programs, particularly around the Altgeld Gardens housing project.

After three years, Obama left Chicago to attend law school at Harvard, but he returned to work as a summer associate at the Loop office of Sidley Austin LLP . There, he met a full-time associate named Michelle Robinson; in 1992, she became Michelle Obama, and the newlyweds moved to Hyde Park. Obama took a position on the faculty of the University of Chicago Law School. He continued working as a lecturer there until his election to the U.S. Senate in 2004.

While there is evidence to suggest that he has traveled north of the Loop on a few occasions, Barack Obama's Chicago is very much on the South Side of town. While even Bridgeport native Mayor Richard M. Daley will play both sides of the baseball fence for political purposes, Obama is an unabashed White Sox fan, so leave your Cubs gear at the hotel.

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If Barack Obama had eaten at half the number of restaurants that claim him as a former regular, the White House would have to get some of William Howard Taft's old suits out of storage. Nevertheless...

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(Travel topic? Itinerary?)