This past weekend, Matt and I met in Chicago to celebrate our 5th anniversary! We had been planning this trip for a while. We wanted to meet somewhere besides our respective homes on the East and West Coast. Matt visited Chicago a couple years ago for a boys’ weekend and I had been for a conference, but neither of us felt like we fully experienced the city.
It was the first “vacation” we’ve taken as a duo so we were very excited. Both of us did a bunch of research on the activities and, most importantly, the restaurants we wanted to try. By the time April rolled around, we developed a full-fledged itinerary. I may have gotten carried and scheduled us down to the hour…
The main things we wanted to do included visiting the Art Institute, going on an architectural boat tour, and check out the view from the John Hancock building. Unfortunately, we didn’t end up making it to the lounge atop the Hancock, but we loved the museum and boat tour.
In all honesty, our main focus was the food. Chicago is a total foodie city with all types of cuisines and bars. We seriously framed every day around where we wanted to eat (more posts to come).
My favorite part was, obviously, the meals and the music. We got really lucky – a good friend of mine from school connected us with her sister whose boyfriend works for a hospitality group in Chicago. All of our top restaurants and more were under this group’s management! What are the odds? He also recommended great places for us to experience live music. We enjoyed everything from blues, to big band jazz, and a piano competition. I love jazz, and just live music in general, so I was in heaven! We loved the speakeasy atmosphere of a lot of the restaurants, bars, and clubs we checked out. It really did feel like we stepped into a different time.
I’m not sure what I was expecting from the Windy City, but I was blown away by how cheerful and dynamic it was. We felt so fortunate to be introduced to incredibly kind people who were happy to share their favorite Chicago recommendations. Despite the heavy rain and wind toward the end of our trip, people were bustling about the entire weekend. I love that type of energy. It felt much more urban than D.C., yet not quite as intense as New York City. It was impressive, yet approachable. At the end of the weekend, it was tremendously difficult to leave. And, I think that’s when you know you’ve found somewhere truly special.