Visiting Chicago Family Style

The hubby and I are excited about our upcoming mini-vacation to Chicago. In less than a week we will be making our third trip to the Windy City. 

Our first visit was a weekend getaway many years ago with some great friends. This trip was special for many reasons. First, we took a train from St. Louis to Chicago. How cool is that?!? 

We also experienced our very first slice of Chicago deep dish pizza. A little taste of heaven! We explored the Navy Pier and walked along the Magnificent Mile. It was a great time.

Several years ago, when the kids were in high school, we decided to make our next trip to Chicago. This was going to be a fun filled 5 day family vacation jam packed with lots of our favorite things.

When planning any trip I always think about not only where we are going but what we will be able to see and do while we are there. We really hit the jackpot with this vacation! I found things that all of us loved and many awesome memories were made.


For this trip we stayed at a hotel just off the Magnificent Mile. It was in a great location for all of the things we wanted to do. We could easily get on the subway and could also walk to the Navy Pier and the theater district. Our home away from home was also located along the river directly across the street from Harry Caray’s Italian Steakhouse. Being huge baseball fans this was a real treat. 

Speaking of baseball, another great thing about Chicago is that they have not one but two MLB teams. Being that we are die hard St. Louis Cardinal fans that means I have a little bit of a love/hate relationship with Chicago.  

But for this trip we put aside our disdain for the Cubs in order to experience an evening of baseball at historic Wrigley Field.  Perhaps I am somewhat biased but I wasn’t overly impressed. The ballpark is very small and obviously old. But a night of baseball is always a good idea in my book so I’m glad we had the opportunity.

We were also lucky enough to have a chance to see the Chicago White Sox play. This was a newer ballpark and was very fun. The night we were there was a theme night that added more fun to the experience. 80’s hair bands was the theme and people went all out with their costumes. It was awesome!


That tied in very nicely to another one of our activities on this trip.  I was probably the one most excited about this one, but we all had a great time watching Bon Jovi in concert at Soldier Field! Along with Kid Rock, they rocked the night away! Awe, the memories! 

Our last night in Chicago we went for a little bit of culture by going to the theater district to watch a musical. Of course when it’s Shrek – The Musical I’m not sure it was a lot of culture! My kids had loved the movies so it was an experience we could all enjoy.

They also happened to be filming one of the Transformers movies while we were in Chicago. Seeing the props laying on the streets was pretty cool and when the movie came out it was exciting to see how it all came together.


While our nights were filled with amazing experiences, our days were filled with walking. LOTS of walking! This was before the Fitbit era but I’m sure I would have set a lot of records. We definitely learned that while sandals may be cute, tennis shoes are MUCH better for trekking around the Magnificent Mile.

We explored the Navy Pier and ate lunch at Bubba Gumps. We, of course, also had some deep dish at Pizzeria Uno’s. It is said that this is the original home of authentic Chicago deep dish, but who knows? All I care about is the awesome pizza!


Thinking about this trip has brought back so many memories and made me even more excited about our upcoming getaway. We hope to visit some of our favorite places while also having new experiences as we just keep collecting memories as we go.

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