I left for Chicago on a foggy DC morning. Not looking forward to the cold, and traveling alone, I had to make a list of things to occupy my restless, wander-lusting spirit during my stint in the windy city.

Number one: see a show at the famous Second City improv theater. Two: eat deep dish Chicago style pizza till I burst. Three: walk in the footsteps of a young couple poised to one day assume the highest office in the land.

While working an exhausting senate campaign for a few weeks, I made the time to catch a Second City show and grab a box of Giordano’s deep dish pizza– which by the way was completely worth risking bathing-suit season for.

Then on a whim, a former (then Senator) Obama staffer offered to give me a tour of Barack’s old stomping grounds. I of course obliged. Who wouldn’t want to walk the path of this young couple, who years later gracefully won over the American people two terms in a row.  Now that’s priceless.

From their first home to Barack’s favorite restaurant, take a glimpse into the beginning of President Barack and First Lady Michele Obama’s extraordinary journey to the White House.

obama young first home Chicago
The young couples first home.
Obama young barber shop Chicago
Barack’s favorite spot for a haircut.
Young Barack’s favorite restaurant.
Obama young first apartment
Young Barack’s first bachelor pad. (Second floor.)