Long Weekend in Chicago

October autumn weather took me a bit by surprise seeing that I’m from the south. The Windy City was exactly as its nickname suggests, windy. My girlfriend, Kendra, and I decided to road trip 11 hours to Chicago, Illinois over Indigenous People’s Day/Columbus Day weekend. It was my first time visiting Chicago and we accomplished quite a lot in our short time there.

We left from Alabama shortly before midnight on Friday night and only stopped for gas and to swap drivers once in the middle of Indiana somewhere. Upon arrival in the city, we had a few hours before we could check into our Airbnb. Despite the rugged few hours of car sleep each of us got, we were both still pretty drained. No matter, it was daylight, around 10:30am on Saturday, and we needed to eat something and wanted to explore a little bit. Our first stop was at the Chicago History Museum cafe called North & Clarke Cafe. As we were walking toward the cafe from the designated parking lot, we witnessed a near car accident and saw the driver aft of the other shout ahead, “Learn how to f***ing drive!” It was a hilarious first impression of the city and I will not soon forget it.
Windswept, we entered the cafe and split a sandwich and got coffee to re-energize ourselves before entering the museum proper. My general ignorance of Chicago was pretty high, so learning all about the Chicago fires, the fact that the city was named after a Native American word that loosely translates to “stinky onion”, and that the first skyscraper in the world was built there was a studious learning experience. We spent a couple hours musing through the two story museum until we had our fill before heading back to my car in the museum’s lot where we were accruing an expensive paid parking pass.

Cool street art

We still had about an hour and a half before we could check into our Airbnb and we both desperately wanted rest. So naturally, we drove to one of the beach exits heading north where you could park along the road and reclined our seats and tried to nap for a bit. Once I got the alert on my phone that the Airbnb was ready, we looked up to see a boy standing on top of the car parked in front of us using a selfie stick, it was comical through fuzzy vision.
Our quaint apartment resided in the neighborhood of Andersonville, and once there we slept hard. The short amount of driving I did in Chicago was enough to put me on edge, so I did not drive my car again until we left the city a few days later. To any local Chicagoans that read this, you guys are some kind of fierce to drive the way you do.
After several hours, Kendra and I woke up hungry and decided to eat at Hopleaf Bar, a Belgian style restaurant and bar with fantastic food and delicious beer that the wait staff happily paired with our meal. We split a charcuterie board and the Amish chicken that was fried with aioli. We each tried a couple different beers but could have easily spent hours there tasting the wide variety from their taproom. Below is a brief list of what we tried:

  • North Coast Brother Thelonious
  • Poperings Hommelbier
  • St Bernardus Wit
  • Palm Spéciale

Sunday morning we woke up late and properly rested. We got an Uber into downtown and had brunch at Atwood. I had an appetizing omelette and Kendra had Smoked Salmon Benedict that would make us crave it later on. This day was all about exploring and getting into what the city had to offer. Once brunch was finished, we walked to Millennium Park towards the Bean (actually named Cloud Gate, I had no idea). Among the other tourists, we took several photos, had photos of us taken, and took photos for others.

Cloud Gate

Continuing through the park, I took a handful of pictures here and there but we mostly kept on towards our next goal, the famous Sears Tower (now renamed the Willis Tower, I learned a lot on this trip). We waited in line for probably an hour before getting to the elevator inside the tower that would take us up to the widely coveted photo spot on the Willis Tower Sky Deck where you can pose in a glass box hovering 108 floors above the pavement below.

iPhone picture on Willis Tower Sky Deck

Once we descended from our sky deck photo op, we continued toward our next adventure of an architectural river tour provided by the Chicago Architecture Foundation Center. We boarded the sizable boat and sat on the open aired second story to view the beautifully crafted buildings that Chicago had to offer. As the boat took us down the Chicago River, our tour guide and speaker, who was a volunteer from architecture foundation itself and was purely there out of eagerness to educate everyone about the city skyline, we stared in amazement. Kendra loved the river cruise and took in all the sights while I took video snippets and photos throughout the ride. Seeing buildings designed by Frank Lloyd Wright in his art deco style was fascinating as well as other architects’ impressive structural expressionism styles.

Once the cruise was over and we got our fill of tasteful skyscrapers, we perused for dinner. We walked several blocks and stumbled across Pinched on the River, a new Mediterranean Grill restaurant. The restaurant itself is subterranean from the entrance on the street and you order at the counter then sit. I got a seasoned beef pita roll that outstanding and Kendra had a chicken shawarma pita roll with spicy kalamata hummus. With Kendra’s meal she also got a frozen rosé drink topped with blueberries and rosemary that had a lovely flavor. Since it wasn’t busy at the odd time that we arrived, the owner spoke to us for a bit and welcomed us to the city with a few fresh beignets that could rival those from New Orleans’ Cafe Du Monde.

Backtracking after dinner, we moseyed toward London House Bar at the recommendation of a friend. The bar was inside of an elegant hotel and the bar itself was high end with an elaborate view of the city and river at night. Our cocktails were only so-so but I took a few night shots on the balcony. We quickly did some googling to find our next stop before going home for the night and found this hole in the wall dive bar called Mom’s Place. Similar to the Mediterranean restaurant earlier, it was fairly vacant. We asked the bartender for a local beer that he liked which ended up being Heileman’s Old Style, and we enjoyed a few. Kendra insisted that I try Jeppson’s Malört since its origins are in Chicago and she and the bartender had a laugh at my facial expression when I learned that it tasted less than favorable to me. Kendra and I took a few silly polaroids of us there while we enjoyed ourselves and carried on. Our extended stay came to a close and we Ubered back to the Airbnb so we could take on our last day on Monday.

The London House Bar balcony photo doesn’t do the view enough justice

On our last full day, we proceeded into the Loop to get some pizza; we couldn’t leave Chicago without trying some authentic deep dish. We stopped at one of the few Giordano’s Pizzeria locations and got a small salad and medium pizza to share, both very tasty. Our last big point of interest was really something that meant more to me, the Adler Planetarium. I hadn’t visited a planetarium since I was in my early teens and I LOVE space. Learning about a few famous astronauts, seeing old instruments and telescopes that early astronomers used to view cosmic bodies was fascinating. There were a metric ton of kids visiting as we were making the experience a little deafening at times, but overall it was still an enriching experience. Outside of the museum on the skyline walk, I finally took the opportunity to fly my drone over Lake Michigan to get some skyline views and photos of the planetarium. The cerulean blue water looked beautiful contrasting against the silver and grey buildings encroaching upon it.

Drone shot above Lake Michigan of Adler Planetarium
Kendra and I
Once again, photo doesn’t do justice: Aloha Roll, Salmon Sunrise Poke Bowl, and spicy ramen

For our last dinner, we found a place in walking distance from our Airbnb in Andersonville called Blowfish Sushi & Ramen. This place had incredible food, possibly the best of the trip in my opinion. We shared everything so we could get a taste of several dishes. We had calamari, spicy ramen, a Salmon Sunrise Poke Bowl, and an Aloha Roll. The entire ensemble of food was very filling and we left satisfied and happy to have been there.
The following day we checked out of our Airbnb and hit the road to head back home. I made a quick video of a few clips I captured during our short time in Chicago that you can view below!

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