May 7, 2018
It’s Monday morning and I woke up bright and early to fly with my family (Mom, Dad, Sister) and the boyfriends (mine and my sister’s) to Chicago! The TL;DR version of why we were going on this trip is that my dad is in the lighting industry and the largest conference for the industry was taking place in Chicago this year. His company was hosting a huge party at the House of Blues. Never ones to miss a good time, my family and I decided to tag along! I was in Chicago for an overnight trip once in college, but I was excited to be back in the city with my family and with some more time to explore! We arrived around noon and immediately dropped our things at the hotel before heading out for some lunch. We stayed right on the river downtown at the LondonHouse Chicago Hilton Curio Hotel. This hotel was in an old repurposed building and it felt like a really seamless remodel — the rooms weren’t too small despite it being in the middle of a big city.
Our first of many food stops was at Lou Malnati’s for some deep dish pizza. We tried one of each of The “Lou” — my favorite with lots of veggies, garlic, and basil — and the standard Chicago sausage and pepperoni. We assumed it would take a while to come out (they warn you that it takes a long time to bake through all that crust) and we were right. It took 30 minutes. But with all that cheese, it was definitely worth the wait! After pizza, we obviously hadn’t consumed enough calories so we needed some dessert. We found Firecakes and indulged in some donuts.
Next on the itinerary was our first tourist stop, Millenium Park and the Bean! The park is a gorgeous public park that was built to celebrate the third millennium and the bean is a giant steel sculpture. To be honest, I’m not really sure why everyone loves a giant shiny bean so much but it was on the tourist list so we went. We walked over, took some pictures, and soaked in the sun! My mom and sister then broke off for some shopping while I went with my boyfriend, Jay, and my sister’s boyfriend, Austin, to do what we do best — drink cocktails. We started at a spot called The Dearborn where I dug into a drink inspired by Beyoncé (think: strong, honey, and feminist) before attempting to find a rooftop bar. Apparently not such an easy feat — all the ones we had Yelp’d in the area were closed for private events — so we landed at City Winery Riverwalk right on the river. It was so nice to be on the water on a such a sunny day! We hung out there for awhile and the rest of the gang regrouped there for a drink. After a quick change at the hotel, we then found our way to dinner with my dad and his colleagues. We had a FEAST at Madison Bar and Kitchen. My dad was hosting some of his coworkers and other lighting professionals. Business dinners mean lots of drinks, lots of apps, and a very full belly. I tried a few cognac cocktails, and we ate basically everything on the menu including the beer battered cheese curds and duck fat french fries. No diets here. Then we rolled back to the hotel for a good night’s sleep.
May 8, 2018
Day two in the city started with a workout at the fitness center in the hotel. When we checked the weather, we realized that the forecast was calling for 80 degrees and lots of sun — not the 60 degrees we had been expecting (and had packed clothing for). We quickly got ourselves showered and dressed and ran over to the nearest Target to buy some shorts and sunblock. On vacation, I love to find a classic diner to start the day, so we had breakfast at the Pittsfield Cafe. It was in the lobby of an old-school Art Deco office building downtown and felt very old Chicago to me, based on my limited knowledge of Chicago movies, at least. After breakfast we ran to meet up with our architecture boat tour that came highly recommended, hence why I knew our breakfast spot was in an art-deco building. It was a 90min tour up and down the river describing the city’s incredible architecture. I felt like it was a really great way to view the city, and I learned so much about the different buildings and the growth of the city. You can really see how each era was defined by the architecture, from Art Deco to Mid-Century Modern, and how carefully the city was planned.
We followed the tour with a walk to Blommer’s Chocolate Factory. We smelled the chocolate in the air while we were on the boat and we had to check it out. It turns out it was way more of a no-frills chocolate factory than anything set up for tourists but it was still fun and we bought a bunch of chocolate to bring home. Lunchtime was our next stop at another recommended spot called Portillo’s. We had fully dressed Chicago hot dogs (which means, they’re topped with basically everything including a giant pickle spear), onion rings, and a Chocolate Cake Shake.
Yes… I said Chocolate Cake Shake, meaning there was a whole piece of cake mixed up in the shake. Yes, it was the tastiest shake I’ve ever had. After lunch was our shopping journey number two on Miracle Mile (a long road north of the river). This was the busiest part of the city we’d been in but I found Chicago to feel a lot cleaner than NYC. I enjoyed walking around and just taking the city in.
Dinner on night two at Hub 51 was with some friends that my sister and I met on our Birthright trip to Israel last year. We’d had the chance to meet up with two of them in NYC a couple months prior, but the other one we hadn’t seen in almost a year and a half since the trip. It was so fun to catch up on our lives, and I wish I lived closer to all of them. After dinner we headed to the House of Blues for the big reason we were in Chicago — my dad’s business party. His company rented out the venue for a full night of food, drinks, and music (which my dad organized… he even played in the bands!). The House of Blues is the original venue started by Dan Aykroyd, and it was amazing to see my dad up there playing where so many great bands had played before. We had a really great evening and fell into bed late.
May 9, 2018
Day three was our last day but we had to sleep in a little after the long night we had. We ate breakfast down in the hotel since we had a voucher, stored our bags, and headed over to the museum at the Art Institute. I’m not usually a big museum person but there were some cool pieces, like some Warhols, and an iconic Hopper painting (Nighthawk). Then we jumped in a car to our final item on our “To See” list, the Hancock building for a drink at the top. We rode the elevator to the 95th floor to The Signature Room and got a table in the lounge. It was pricey but totally worth it, the views were incredible, you could see basically the whole city and the lake. Most people go up to the observation deck for the tourist experience, but considering admission to that was the same price as the drinks, we figured we might as well get some booze out of it! We then took a leisurely walk back to the hotel before we had to leave for the airport. We stopped at Garrett’s to get some cheese and caramel popcorn (“The Chicago Mix”... so weird, so good) and Stan’s for another donut fix on the way. We took the train directly to the airport which turned out to be so much easier than a car especially as it was getting closer to rush hour. We live in NYC, so we weren’t afraid to take advantage of the public transit, and it was cool to see another subway system.
While I’ve seen quite a bit of Europe, I’ve seen very little of America and I love exploring new cities. There is so much more to do and wider boundaries we could have given ourselves had we been there for longer than just 3 days. But I feel like we did a LOT for the time we had. I can’t wait to visit again.
