Chicago, – what a lovely surprise!

Yesterday, I returned from a fabulous week in Chicago.  My only prior experience with this city was a stopover at O’Hare or Midway airports.  

I never really considered Chicago as a vacation destination. Sure, we all know Oprah is from Chicago and it’s called the Windy City but do you really know Chicago?

Fortunately for me, I had the opportunity to tag along with my husband as he attended the International Association of Chiefs of Police Conference being held at McCormick Place.  Hats off to Chicago, what an amazing feat to host over 14,000 Chiefs of Police from all over the world.  Needless to say, I felt very safe walking around the city on my own.


We flew into Chicago’s Midway Airport  (Travel Tip: If at the airport and you upgrade your seat to priority boarding with Southwest (guaranteed A boarding for $30 a person) don’t pick the first bulk head row of seats when you board.  You can’t have your bag by your feet and there is no tray to use as a work area or beverage holder). 

Since the hotel we were checking into was only 13 miles away, it would be quicker and less expensive to just grab a taxi.

(Travel Tip: The Express Shuttle from Midway to any city hotel is $19.00 per person and it is a shared transfer with many stops) The taxi ride was $20.00 total for Mike and I.  

We really lucked out on our cab driver, he was more like a personal tour guide.  I don’t recall his name, but I do remember he was from Zimbabwe.  He was very entertaining; explaining to us what his first winter was like in Chicago.  He gave us some Chicago history, pointed out historical sites and even great restaurants as we drove down Miracle Mile. (Travel Tip:  Miracle Mile is 13 blocks of the best of the best shopping malls, high end stores, boutique stores, restaurants, bars, and dotted pieces of history everywhere. Bring great walking shoes)

My favorite brand of hotels is Starwood Properties.  We opted to stay at the Westin North Michigan.  A few blocks from the waterfront, 10 steps from Michigan Avenue and on the shuttle route for Mike’s IACP conference.

We had a great room on the 5th floor. The rooms were highlighted with bits and pieces of Chicago’s history mixed with sleek and modern design.  The bed was Heavenly! No, really, Westin’s bedding is the called the Heavenly Collection (you can go to their website and purchase all their items!).

First night in Chicago, what did we want to try?  You guessed it, Chicago Deep Dish Pizza! Only a few blocks from our hotel was famous Gino’s East.  (Travel Tip: Use the services of your concierge. So many travelers neglect to use this free service.  Our Concierge provided us with a voucher and we literally were able to skip the entire line outside, and we were seated immediately, it was great!)

While Mike spent his day(s) at the conference, I decided to venture out and do some touring.  I walked over 9 miles on Sunday exploring this fantastic city.  The buildings in Chicago are each a piece of art. I saw modern, Gothic and baroque style buildings. My favorite buildings being the Chicago Water Towers, two of the few buildings that survived the Great Chicago Fire of 1871.

I walked along the river front (Travel Tip: Chicago is known for its incredible St Patrick’s Day celebrations which includes dyeing the river green.  Book early, the city sells out)

Chicago offers Double Decker and River Boat tours, museums, zoos, galleries and an amusement park at Navy Pier. I have never seen such a Kaleidoscope of eateries in my life.  It’s a beautiful, polite, clean and a great family friendly city to visit. 

 One of the many parks in Chicago that I was able to enjoy was Millennium Park. This park is famous for the modern piece of art called The Bean. 

Before I new it, it was time to pack up or bags and head to the airport.  Usually after a few days away from home, I am ready to get back into my own bed, but this trip was different. I still had so much to discover!


Chicago, I will be back to meet you again!

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