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Week 18 (Continued) - Chicago, Illinois (The Second City)

  • Writer: Danielle McKinney
    Danielle McKinney
  • Jun 2
  • 6 min read

Hello Family and Friends,


Chicago is a great city. It is doing it's thing. I feel like Chicago is a very purposefully built city. They are called the second city not because they are second to New York (even though they are). They are called the second city because after The Great Chicago Fire of 1871 they had to rebuild the city, the second city, on the ashes of the first. Upon rebuilding the city they made sure that the buildings were steel. They have further instituted rules that ensure the water is accessible to all and that buildings can't block the view of the water. While we were there, something was going on where all the pools were having maintenance due to some city mandate. The city is very involved in making sure that the buildings are up to snuff.

Chicago is also very artistic with it's buildings. We took an architecture tour where we learned that Chicago is the location of the first skyscraper. Another style of architecture is Contextualism, where the buildings reflect their surroundings sometimes symbolically and sometimes quite literally. Chicago is on a river so, many of its buildings would curve with the river and have a color that looked bluish green like the river.

The family enjoying the architecture boat tour even on a cloudy day.
The family enjoying the architecture boat tour even on a cloudy day.
Can't see the top of the tallest buildings in Chicago due to cloud cover.
Can't see the top of the tallest buildings in Chicago due to cloud cover.
This building shows a little bit of Chicago's attitude. The owner found out that the building wasn't mentioned on the architecture tour, so he put a grid of the city on the side of the building and marked his building literally putting himself on the map so that it would be mentioned on the tour. It worked.
This building shows a little bit of Chicago's attitude. The owner found out that the building wasn't mentioned on the architecture tour, so he put a grid of the city on the side of the building and marked his building literally putting himself on the map so that it would be mentioned on the tour. It worked.
Just more beautiful skyline views
Just more beautiful skyline views

However, Chicago is a little bit crazy. It's river is not swimmable...yet. It has had a long history of the river being a cesspool (think Paris before the 2024 Olympics). That is actually one reason why The Great Chicago Fire was so destructive. The people didn't think the fire would cross the river. However, there was a thick film of oil on the river, so the river literally caught fire. Chicago's solution to it's dirty river was to change the direction that the river flowed. I'm really not sure what type of person just decides the river should flow the other direction and then manages to actually do it! Just insane!


Traveling with a teenager makes for a little different travel experience. First and foremost, she helps me take pictures, which is super nice. She also get's recommendations from different sources than Brett and I. Whenever we get to a city and are looking for things to do we will Google recommendations and look on Trip Advisor. Sarah, the teenager, will get her recommendations from Instagram and Tiktok. I'm not mad; our first stop in Chicago was a Tiktok restaurant recommendation. It was on the water and the decor was Instagram worthy.

Our view for dinner our first night in Chicago at Beatnik on the river.
Our view for dinner our first night in Chicago at Beatnik on the river.

Of course we tried other Chicago staples such as the Chicago dog from Portillo's. Brett was a fan, but I think I was too hungry that day to really taste it. We also had a deep dish pizza from Giordano's. All the locals recommending skipping the deep dish and going for tavern style, they were right. We tried a Chicago deep dish in Chicago and it was "meh". (However, I should have mentioned the Detroit style in Detroit was excellent.) We never did make it to the Chicago style popcorn. Ah man, we'll just have to come back.


Sarah and I took a day and went shopping along the magnificent mile while the boys went trapping around town for bike gear. We started the day at the Starbucks Reserve Chicago . I am not a big Starbucks fan, but when it is five levels with a rooftop deck, you have to check it out. I'm glad we did, because it was better than a regular Starbucks.

Girls brunch on the rooftop deck at the Starbucks Reserve
Girls brunch on the rooftop deck at the Starbucks Reserve

We also went to millennial park and checked out the Chicago Bean. Had no idea that this was a thing(I obviously don't use Tiktok), but it's actually very cool. When I first saw it, I was like "Oh look, they glued the skyline on it". Sarah laughed at me and let me know that the skyline was not glued on, but a reflection. The bean is essentially a huge mirror! I mean not really, but yes. I'm glad Brett wasn't with us as he would have judged us for getting all excited about a mirror.

You can see the city in the reflection of the bean.
You can see the city in the reflection of the bean.

Sarah taking a reflected selfie in the bean.
Sarah taking a reflected selfie in the bean.
The Lurie flower Garden in Millennium Park
The Lurie flower Garden in Millennium Park
Captured a little bunny rabbit hopping around Millennium Park in Lurie flower garden
Captured a little bunny rabbit hopping around Millennium Park in Lurie flower garden

While walking around Millennium park, I was actually attacked by a bird for the second time. The first time was on a run along the Detroit River in Windsor. In Windsor I just assumed I was too close to it's nest or that it mistaked my fluffy hair for some good material for it's nest. But when the same looking bird grabbed my head in Millennium park, I had to look into this creature. The culprit is a a red winged blackbird. It is known to be quite aggressive and very protective during the breeding season, which is now. I could not find any connection between my afro and it's behavior, but me and this bird are going to fight!

My new archnemeses
My new archnemeses

We ended the day all together with Art on the Mart. It's a light show on the river. The projector takes a 3D scan of the building so that the light cast does not disrupt the people who work in the building.

They even add music to the light show.
They even add music to the light show.

With all of Chicago's beautiful tall architectural buildings comes a plethora of rooftops bars. Sarah was so kind to offer to babysit Atlas so that Brett and I could have an adult night. Of course with so many rooftop bars Brett and I decided to go bar hopping. The plan was to grab a drink, grab a photo and then move on. Our first stop was Cindy's which boasted beautiful views of the city and the skyline.

The view from Cindy's overlooking Millennium park. The view is the only thinking good at Cindy's. The drinks were terrible and the rooftop deck is small with no seating(half was being renovated).
The view from Cindy's overlooking Millennium park. The view is the only thinking good at Cindy's. The drinks were terrible and the rooftop deck is small with no seating(half was being renovated).

We are one drink in and moving onto the next bar. I get this great idea to rent scooters to head to the next bar. We have had a few days of 15,000 steps and our old ankles are feeling it. And we always see these scooters in the city, but can't ride due to having Atlas with us. So it's just Brett and I and we rent scooters: download the app, put in the credit car information, figure out how to ride them and onto the next bar.

Cerise is the next rooftop bar. The vibe was much better here. The rooftop deck had chairs outside and there was a DJ playing some decent tunes.

View from the second rooftop bar. Two drinks in.
View from the second rooftop bar. Two drinks in.

We hopped back on the scooters and head to the third rooftop bar, The Wit. The Wit had a cover charge, but the it was the best rooftop. There was a DJ and a dance floor. Brett and I met a dermatologist and her boyfriend from Charlotte who wanted to go bar hopping with us. We also met an immigration lawyer, she's on the good side, who has two little girls and is also making travel plans to Europe. We tore up the dance floor for most of the night. Brett and I were having such a great time that he decided to get another drink (I stuck with water). We were meeting people, having a great time and then we weren't. There is no third picture because Danielle is a light weight and needed to go home.

Even though we aren't looking at cities as a place to live, Chicago is definitely on the list. Brett is looking for bikes for us to ride as we venture further west and into more national parks. So we stopped at this one bike shop in the Old Towne neighborhood of Chicago. Brett goes into the bike shop, Sarah walks up the street one block to a Starbucks for coffee and I am waiting in the car with Atlas. Across the street there was an elementary school that was rated number two in Chicago and the top 10% in the state of Illinois. Since it was a Saturday and school was closed, multiple people had their dogs off leash on the baseball field attached to the school. We also saw some nice single family homes when we were driving around the block to find parking for the bike shop. All this to say, we aren't even looking for a place to live and we easily found one neighborhood in Chicago that would work for us. Even my very suburban goddaughter, Sarah, called it her favorite city (of course she hasn't been to New York, so her experience is limited).

 
 
 

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