Two days in Chicago on my “living like Oprah” vacation

Posted on Posted in Activities/Experiences, Chicago, Restaurants, Travel
Chicago "Bean" image
Chicago “Bean”

For all of the international travels I have done, there are a few U.S. cities that i am a bit embarrassed not to have visited yet – Chicago was one of them.  The flight from Philadelphia is short enough, there are two major league baseball teams and a plethora of foods, shopping and attractions to definitely entertain me and yet it remained elusive to me…until my “living like Oprah” vacation which involved a connection in Chicago from Tucson which, to me, was a sign that i needed to stay a few days. I would have two days in Chicago in April.

My day started at Miraval in Tucson with a morning desert hike followed by the rock climbing wall and a few hours later, I would be checking into my luxury hotel, The Peninsula, as I transitioned from the serenity and warmth of the desert to the familiar pace of a city.  I would see that the cold and windy reputation extended to the weather only, as the people I met were very friendly and helpful.

My schedule for Chicago for two days would include:

Chicago Architecture Foundation walking tour – on the cold, windy, rainy day, this tour tested us against nature (note to self, nature always wins).  The guide was a pro and easily guided us inside buildings along the tour in order to feel a bit of heat to warm up. The architecture is so impressive, I often forget to look up in cities to see how amazing the structures are detailed.

Chicago walking tour
Chicago -a mix of architecture

Art Institute of Chicago – definitely a highlight especially on a rainy day.  The wonderful permanent collection as well as special exhibitions allows you to explore many aspects of art.  This was such a treat and you are allowed to take photos (awesome!).  I was a kid in a candy store taking photos of everything especially the modern art which continues to spark interesting discussions (arguments) with friends (more on this later).

Why Knot Ynot Type Art
Type Art at the Chicago Art Institute

Second City (comedy) – a cab ride from downtown, the concierge arranged a seat for me at the show. Famous for the alumni that Second City has turned out, I laughed a lot that night and wondered if i would see these comedians reach a new level of success when i could say “I saw them when…”

Navy Pier (empty, rainy, cold during my visit) – I could envision the warmth of the summer teeming with people enjoying the many restaurants, sailings from the pier and the boardwalk atmosphere with rides, attractions and cotton candy.

Chicago - Navy Pier
Chicago – Navy Pier

I was lucky to connect with friends of friends who quite generously gave me a quick driving tour of the city after our fantastic dinner at the popular Mexican restaurant Topolobampo (definitely need a reservation).

My quick two day visit provided me enough of a taste of Chicago to know that I will be back for a proper visit (hopefully with some baseball and maybe to see the infamous green river!) as it hit all of my requirements – easy to navigate by walking, varied tour options, amazing restaurants and boutique hotels.

Chicago River
Chicago River


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