Twenty Something: The Insider’s Chicago Tour

Follow us on a tour of the First Couple’s old stomping ground…

Young Barack's favorite restaurant.

Young Barack's favorite .

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 madly in love.

Second City’s show was sidesplitting and my Giordano’s deep dish pizza was completely worth risking bathing suit season for. But walking the path of a young couple– who came from humble beginnings to eventually work their way up to the highest office in the world? Now that was priceless. Follow me as I walk down President Barack and First Lady Michele Obama’s footsteps in the beginning phases of their extraordinary romance. 

Young Barack's first bachelor pad. (Second floor)

Young Barack's first bachelor pad. (Second floor)


Barack's favorite spot for a haircut

Barack's favorite spot for a haircut


The young couples first home.

The young couples first home.

You’re welcome Twenty Somethings! 

 is the author of , a social diary blog where she sounds off weekly on dating, D.C nightlife and events, career etiquette, and more. During the day, Ursula stays in step with the pulse of DC with her work as a Deputy Press Secretary on Capitol Hill. Follow her on twitter @urdiggy.


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1 Response

  1. Christina says:

    Great footsteps to follow. Amazing how a feature about Chicago and the First family can allow me to invision my favorite things!

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