Since I’m half asian, I am the best (worst) person to travel with because I take a million photos. Even though we were only gone for a long weekend, in order to properly document our trip, I’ve decided to dedicate a separate blog post to each day so not a single selfie or slice of pizza can be forgotten. This trip was extra special to me not only because neither of us had visited the Windy City before, but because this was my first vacation with someone that didn’t include family. My first real vacation at the age of 28? It’s true.
I usually take a trip to Michigan in the summer (favorite place in the world) but I missed it this year, so aside from a weekend at Pawley’s Island, I haven’t taken any vacation time this year. Whoa… just the thought of that sounds horrible. Michael and I decided a couple of months ago to visit Chicago after I asked him if he wanted to go to DC one weekend. Since he’s a big Cubs fan, I was going to get him tickets to see them at Nationals Park back in June but I was the only one who thought that was a good idea. “Nope, if we’re going to see them, we’re going to Chicago.” Oh okay! And off we went.
We stayed at an Airbnb in Lakeview/Wrigleyville that had the best views of the city. It was a studio apartment on the 52nd floor of a high-rise overlooking Lake Michigan on our left, downtown Chicago straight ahead, and Wrigley Field on the right. This was our first time using Airbnb and I can’t say enough great things about it. After a million open tabs and weeks of searching for a hotel, this was perfect for us.
After a 4:45am alarm and $9 worth of overpriced and terrible iced coffee at the airport, we flew in early on Thursday to get the most of our long weekend. About two minutes after being in the city, I realized that maybe pubic transportation and I are not meant to be. I felt overwhelmed trying to navigate the blue line (seriously, its only one train and I just couldn’t), felt claustrophobic on the bus, and almost gave up and spent $15 on an uber just to get us to to our destination. We powered through and after an hour, we arrived at our apartment for the weekend, where I ooh-ed and ahh-ed over the view for a solid 15 or 20 minutes. Once I was done, we headed to brunch at the Bongo Room in Wicker Park where I nibbled on a breakfast sandwich the size of my head while Michael got white chocolate and salted pretzel pancakes AKA diabetes on a plate. With absolutely no time to waste not eating, we fulfilled my dream of having ice cream at Jeni’s right across the street and made our way downtown to be tourists at the ever-so-famous Bean. Touristy as it might be, I loved it, and obviously, when in Chicago, you take a selfie at the Bean. I think you’re just supposed to, and since we are law-abiding citizens…
We wandered around Millennium Park for a bit before heading back to get dressed up for an-almost-dinner-date with Michael Jordan. We actually ended up at here (he was having dinner down the street) where I quickly realized that any attempt at sticking to healthy eating was officially over for the weekend. Something I loved about dinners in Chicago was the amount of places that had outdoor tables, all complete with twinkly lights everywhere.
We had a recommendation to skip the top of the Willis Tower but instead grab drinks at the Signature Room on the 95th floor of the John Hancock building. After full bellies of fried chicken, we headed here for expensive drinks but an incredible view of the city. It. was. magical.
Chicago is definitely a city that DOES sleep, and after walking outside onto surprisingly empty streets at midnight, we headed back to rest up for the most exciting day. After all, we did travel 800 miles for a baseball game…
I’ll be back to share more pictures, including the most photogenic and delicious ketchup-less hot dog I ever did see.