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.
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).
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.
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.