Chicago is a short six-hour drive from Cleveland and was the perfect road trip destination to celebrate my birthday weekend. We’ve been to the Windy City a handful of times, but I was excited to get to explore even more.
Day One: Travel, Art, and Good Eats
We got on the road and head West towards Chicago from Cleveland. This is going to be one long, boring drive through a lot of flat land but the drive goes quickly.
We arrive at our hotel Kimpton’s The Grey, a hotel in the Loop that we primarily booked for the amazing and huge soaking tub but also because we love Kimpton hotels. Our room is huge and the hotel is gorgeous. I am super excited about soaking in the tub at the end of the day!
After settling in and relaxing in our hotel room, we head out to visit the Art Institute Chicago. It was an incredible museum full of classics we’ve never seen in person before. Amazing and well-known works by van Gogh, Seurat, Dalí, Hokusai, Hopper, Warhol and so much more.
The Obama presidential portraits were in town in a traveling exhibit and it was really cool to see in person. Fun fact, this is also the museum that Ferris Bueller and friends visit in Ferris Bueller’s Day Off.
After hours of getting our art on, we found a nearby restaurant across from Millennium Park that did not disappoint. Dinner at Acanto was a memorable, delicious, and happy last-minute discovery. On the walk back to our hotel we pass the street sign for the start of the famous Route 66, now we can say we were at the start and the end in Santa Monica. I took some photos of Chicago streets at night with my Fuji x100v, a small mirrorless camera I bought for travels since I oftentimes don’t want to lug around my Canon DSLR. Got some great, moody nighttime shots on the walk back.
I ended our evening soaking in the amazing tub with my Air Pods and a book on the Kindle. A perfect way to end the day.
Day Two: Rainbow Cake, The Bean, and Boat Ride
Today is my birthday and we are on a mission to get a slice of rainbow cake. Our hotel was a short walk from Goddess And The Baker’s Wabash location. We got breakfast and I got a slice of their well-known rainbow cake, yum! We ate our breakfast while watching the L train go by on the raised tracks. As a city girl, I love these views.
After breakfast, we make our way over to Millenium Park for an obligatory visit to Cloud Gate, or “The Bean”. It’s such a fun tourist thing to do that I don’t even mind the large groups of people. We walk around the park and get stuck in a short rainfall before we drive to Randolph Street to explore.
It’s time for a late lunch and we put our name on the list at Au Cheval. While waiting, we check out the sugargoat and split a chocolate chip cookie. Our wait is up and we head back to Au Cheval, a small, dimly lit diner with major ambiance and delicious burgers. Afterward, we find Jeni’s Ice Cream and we get free ice cream since it’s my birthday. We love Jeni’s!
Our next stop is to check out the shops in Lincoln Park. I find some new shops I’ve never heard of before. Some classics I love, and the always exciting finding shops for stores you’ve only ever seen online. We perused the shops on Armitage Ave to spend some time before our reservations for a sunset cruise. Some of my favorite shops we visited were top drawer, Marine Layer, Lush, Rothy’s, Gorjana, Kiehl’s, and Paper Source. Some other great shops we visited were Aesop, Allbirds, Outdoor Voices, Parachute, and All She Wrote. I could have spent a lot of time just on this street alone but we had a cruise waiting.
We get back downtown and struggle to find the parking closest to the boat we had reservations on. I had booked a Sunset Cruise through Wendella. I must not have paid attention because I thought it was an architecture cruise during sunset. However, it was actually a cruise that took us out onto Lake Michigan. Oops! It was still a lot of fun and well worth it for the views.
Chicago has an incredibly dense shoreline of buildings and skyscrapers that makes for some amazing views. The most interesting part was waiting for the locks to open. The river pours into the entrance of Lake Michigan but you have to wait for the water levels to even out.
After our cruise, we have reservations for dinner at Nonnina for my birthday dinner. We have a tasty cheese board, salads, and Italian fare and then call it a night. Tonight I soak in the huge hotel tub with a bath bomb I bought earlier at Lush. Another perfect end to the day.
Day Three: Shopping and Chicago Fare
Slept in again and have a late breakfast at Stax Cafe, a spot I heard lots of good about and we have some delicious pancakes before making our way to Chicago’s West Town neighborhood to check out Lost Girls Vintage, a shop I follow on Instagram and really wanted to check out while in town. We also check out the neighboring Paperish Mess shop that had lots of fun paper goods and accessories.
Next, we drive over to Wicker Park for more shopping. We stroll up and down N. Damen Ave and N. Milwaukee Ave and visit many of the shops. Some highlights were: Shinola where I bought a monogrammed journal and Fjällräven where I bought a new backpack. Some other notable shops were Northface, Marine Layer, Diptyque, Levi’s, and a really cool book store whose name I forgot.
The sun was out in full force so we decided to go get lunch at Portillo’s, a Chicago institution. I was not a fan, but Nathan enjoyed his. I ended up with a salad which was really good.
The hot day and shopping wore us out so we went back to the hotel for a long nap. When we woke up, we thought we would try to visit the 360 Observation Deck at the Hancock Building. Unfortunately, the tickets had sold out for the day. We decided to just get dinner and wrap up the evening so we drove out to Lou Malnati’s pizza. Sadly, it was another disappointing restaurant spot. Many told us this pizza was the best, but the crust was so hard it hurt my teeth. (I still think Giordano’s has been the best of the spots I have tried on previous visits. )
Day Four: Fish Ice Cream, Failed Beach & National Park attempts
We slept in and decided on a late breakfast at Elephant and Castle so Nathan can have an English Breakfast. After breakfast, we drive around the city to visit for a few photo ops, but a street fair prevented that.
We then tried to visit Oak Street Beach but parking was impossible so we gave up. We seem to have this problem every time we visit, so hard to get a parking space. Next time we’ll plan better. There was a shop, Taiyaki, that had cute, Instagram-able fish-shaped ice cream cones and I had to try one.
We planned on visiting Indiana Dunes National Park since it was on the drive home. Unable to find parking, we try the neighboring state park and find a spot. We did get a parking space but only took a quick walk around before getting back on the road.
Overall we had a really great time even though the end of the trip sounded like a lot of bummers. Not every trip is going to go 100% perfect, and that’s okay. It’s still fun to travel and experience somewhere new.