I Left My Heart in the Windy City

A few months ago my parents and I were trying to decide where to go on  a family vacation. Dad was the one to suggest Chicago and it was a place I’d be wanting to go so last Thursday we took off for the Windy City.

I don’t always love big cities. I’ve never really been a fan of New York (sorry NYC friends) because I find it cold, dark, rude, dirty and just too overwhelming. I thought Chicago might sort of be that way. Much to my happy surprise, it wasn’t anything like that. It has some of the things I like about NYC without the things I don’t. It was a clean city with interesting architecture. People were friendly and never in a rush. And you can’t beat a city that has beaches.

After we arrived on Thursday, we dropped our bags off at our hotel, grabbed lunch at a nearby cafe and headed down to Grant Park and Buckingham Fountain (or the Al Bundy Fountain as I call it since it reminds me of the opening credits from “Married with Children”). We walked around there and down near Lake Michigan. There was a great path running next to the lake. Even though it was pretty cloudy that first day, there were a number of people out biking and running along the path.


Skyline from the fountain


Buckingham Fountain


Hmmm, which boat should be mine?

After a long day of traveling and walking, we headed back to the hotel and ordered a pizza for delivery from Toppers. We didn’t have deep dish, but it was really good.

The next morning we took a cab over to the Navy Pier. It was an absolutely gorgeous day. We looked through a bunch of the shops and Mom and I walked to the end of the pier to take in the views while Dad did some people watching. We grabbed some lunch at Billy Goat Tavern and had some cheezborgers. See the SNL skit on the website if you don’t get it.


The view from Navy Pier


Another view of the skyline

From the Navy Pier we cabbed it over to Wrigley Field to take in the Cubs-Cardinals game. We drove along Lake Shore Drive past some of the beaches. It was still hard to believe that there was sand anywhere near a major city road and close to the skyline. I think it was at that moment I started to fall a little in love with Chicago. I would give anything to be able to walk to a beach anywhere near D.C.

I figured we’d be getting to Wrigley pretty early so I was somewhat surprised to see how packed it was. There were a lot vendors out and already a ton of people there more than an hour before the game. As the type of person that is always 10 minutes early, I was happy to see how many people were already there soaking in the atmosphere. When you go to the historic stadiums like Fenway or Wrigley or the old Yankee Stadium, the local neighborhood becomes part of the experience. People were everywhere, taking in some pregame entertainment in the form of a small band or going to one of the local dive bars. I love that.

One of the other nice things about a place like Wrigley is how intimate the stadium feels. You are so close to the field compared to the newer stadiums.

I enjoyed a few beers and got a Chicago Dog (yum) and believe it or not, the Cubs won, ending a streak of shutouts.


A little pregame entertainment.




Cubs win! (Please excuse my finger in the picture.)

The next day we headed down to Michigan Avenue to hop on a sightseeing boat to view the architecture of the city and then to view the skyline from the lake. We had yet another gorgeous day. We learned a lot about the history of Chicago and our tour guide was pretty funny. He even kind of looked like Daniel Tosh. While we were on the lake we could see some of the air show which was going on nearby. That was pretty awesome too.



Kind of dark but that’s the Willis Tower, which used to be known as the Sears Tower.



View of the skyline while we were waiting to go through the lock that connects that river and the lake.



The photo is a little tilted because it was kind of choppy that day. Still one of my favorites from the trip though.

After the boat tour, we walked over to Millennium Park to check out the bean, or Cloud Gate as it’s really called.


Millennium Park


The bean!


Selfie in the bean


Crown Fountain with some of the skyline in the background

We walked over the Art Institute of Chicago and checked out the gift shop. Since I’m a spoiled D.C. resident who never has to pay for museums, I was outraged at the $32 entrance fee for the museum, The gift shop is good enough for me, thanks.

Dad was a little tired at this point so he hopped in a cab and headed back to the hotel. Mom and I walked up and down Michigan Avenue to check out some of the stores. We sat down at an Irish pub for a couple of drinks and some food and then walked back to our hotel for the night.

The next morning Dad treated us to breakfast and then it was off to the airport. It’s always amazing how fast vacation goes. I loved just about everything this city had to offer: the architecture, the lake, the river, the food, the people. We had some awesome cab drivers from all over the world. A few of them were studying things like physics or computer science at one of the local universities. I’m convinced every cab driver we had was way smarter than I could ever hope to be.

Bottom line: Chicago is one of the best cities I’ve ever been to. I daydreamed about living there more than once. And yes, I know it’s about -20 degrees there in the winter but I prefer to overlook that. Kind of like you prefer to overlook a loved one’s flaws. I can’t wait to go back and explore even more of the city.

And now that this vacation is over, I’m already looking forward to where I can go next. I’ve got a rough plan for a road trip to the South in December so I can knock off a few more cities on my must-see list…