Have you ever visited Chicago?
Well, I did for my first time this past weekend and my experience was nothing short of incredible.
The idea to travel Chicago began while visiting a friend of mine, Meghan, while she was home in Cleveland.
If you’re wondering the difference between Meghan and Megan, it’s the H.
Meghan is living and working in Chicago and has been for the past six years. Her city living experience allowed us to move non-stop throughout Chicago during my three days there.
As much as we were able to conquer in 72 hours, there still remains a deluge of unseen blocks and buildings I wish to return to when I visit next.
The majority of our time was spent walking throughout the city, however, buses, trains, and uber/lyft rideshares made up the rest of the transportation needed to explore.
Parking Tip
Prior to departing for Chicago, I considered not driving my car and using a cargo bus option. Looking back, I would recommend this to anybody who does not plan on using his or her car outside of the city during a trip to Chicago.
Especially if you’re unfamiliar with the city streets, parking will either be a hassle to maneuver or simply overpriced. Choosing to walk or use public transportation is most likely your best bet when exploring Chicago.
Ready. Set. Go.
Upon my arrival in Chicago, I had a few hours to kill before meeting with my friend Meghan.
With a full head of hair and an empty stomach, I decided to first, get a haircut, then second, fill my belly with food.
First, I would like to apologize to my barber on the regular, Indie. I promise to not cheat on you ever again with another barber, but please understand this was a special circumstance.
Anyways, my boy Daniel from the barbershop was a 20-year old kid who provided me with a $20 cut. He even allowed me to pay with Chase Quickpay. Truly cannot beat it and it came out pleasing my standards.
From there, I found myself eating falafel in Chicago’s Health Foods. Delicious. This small little health food shop was filled with nutritious homemade meals and snacks including many ingredients found in my own kitchen. So, I approve.
Okay, at this point, Meghan finished up her Friday work and it was time to get the weekend started.
CARE FOR A FRESH ROAST?
Beginning from Meg’s perfectly sized studio apartment, we walked until reaching the largest Starbucks (Chicago Roastery) that has five stories inside!
I’m not much of a coffee drinker myself, but this Starbucks location was extremely fascinating to see. Not only that, but the smell throughout the coffee shop made it worth the climb up five flights. There were hundreds of people waiting to be served and scattered between each floor.
Moving on from Starbucks, the next stop Meghan would take me to is the Michigan Avenue Bridge.
Underneath this bridge is the Chicago River. All around this bridge is miraculous city lights, buildings, and skyscrapers.
Pick a direction to look and you won’t need to question if it’s going to be good or not.
BEANS ARE HEALTHY FOR YOU
I hope you brought you’re walking shoes because these feet aren’t stopping here.
Next stop: Millenium Park and a 55 Foot Blue Christmas Tree.
Tis’ the season, right?
Chicago’s most infamous park was lit up with Christmas lights and decorations and included an ice rink filled with skaters.
Oh, how could I forget? Yes, I stopped to see the Bean here, too.
There is no time for slowing down, though. So, pick up the pace!
This meant for another walk over the Chicago River and more cool photos! Thank you to my average “can you take a photo for me” photographer following me around on my trip!
SOMEONE CALL THE DOCTOR
Dinner time.
Friday’s main meal is brought to you by Doc B’s. Originally recommended by my friend Derek, Doc B’s serves fresh food made with local ingredients.
I was highly impressed with the food and you could definitely count on me returning in the future.
The appetizer Meghan and I shared, Housemade Sweet Potato and Guacamole, was one of the best tasting simple appetizers I’ve ever eaten. I definitely plan to make this type of dish at home myself.
As far as Entrees go, Meg and I both ordered different style Wok bowls. I decided on the Filet Mignon which was cooked perfectly.
If you’re thinking the night ends here, well stop thinking and get ready to read because there is more to come!
The next stop was all Meg’s idea.
DA BOOT
As a result, I am proud to say that I attended the 24th annual Christkindlmarket.
Talk about a unique holiday experience. This market was filled with plenty German holiday traditions.
The holiday atmosphere filled the block as well as the smell of German Festival Food. Meghan and I enjoyed a much needed hot chocolate served in German boot mugs.
ABRACADABRA
After warming up for a bit, we had a comedy show to catch at The Second City!
Do you believe in madness?
Because I sure do. Especially after watching the madness firsthand by hilarious performers.
DYBIM was a comedy performance by a group of Chicago performers that highlights the maddening events that surround us in our daily life.
Honestly, I’m not going to be able to describe the comedy I witnessed, so the only way to experience the madness on your own is to show up and see it for yourself! You will not be let down at all! Highly recommended.
Interesting stuff, though. If you check the photos below, you’ll find some recognizable faces in The Second City’s Hall of Fame.
Steve Carell. Chris Farley. Tim Meadows. Mike Myers.
After that, the night came to an end and all that was left was to prepare for another day of walking Chicago tomorrow.
SAT YOUR DAY AWAY
Saturday began with a cold shower just like any other day. I realize that’s not what the readers care about though, so here is a view of Chicago to change the topic.
Before hitting the streets, Meghan and I visited her friend Natalie’s apartment. Indeed I performed a demonstration on how to take a cold shower.
Now the real sites get seen.
MAKE PEACE. NOT WAR
The first adventure of the day starts at The Art Institute of Chicago. More specifically, the Andy Warhol exhibit that is currently being featured at the gallery.
Let me do my best to walk you through the exhibit in a timely fashion.
First, you’ll notice an exquisite wallpaper featuring Cow as the primary model.
Moving on, we come across a kid struggling to photograph (Mao + a person photographing Mao) at the same time.
Some of you oldtimers may recognize the Brillo pad boxes in the image below.
Andy Warhol’s take on The Last Supper is included, too, followed by a few skulls.
Last, is a portrait of Thanksgiving some long, long time ago. I’m not sure of the artist as it wasn’t Warhol’s work, but it looked interesting.
And that’s just about all I have for you. From the art institute that is.
I’M SO HIGH
After that, Meghan and I took the red-line train to the John Hancock (DP) building.
This building is the tallest in Chicago and offers what is known as The Signature Room & Lounge located on the 95th and 96th floors.
Sick Views.
Keeping along, now. How about a snack?
Stan’s Donuts was the move. I tackled a blueberry donut and a pistachio donut while Meghan went croissant. Mine was delicious.
Now it’s time to write that letter to Santa that I’ve been meaning to do for some 13 years now.
One Christmas, he stole my dog. He just wasn’t there on Christmas morning. He was old, but my parents said they saw Santa take him with their own eyes!
CHECK IT TWICE
I’m on my way to getting it figured out as you can see below.
Time for a trip to a Cafe Ba Ba Reeba. Spanish cuisine home of tapas, Pintxos, and Sangria.
Our plates were filled with smoked salmon, garlic potato salad, brussels sprouts salad, and a sweet potato coconut soup. When do I not get an item with sweet potato in it? Hm.
I wish I could show a photo, but I forget to take one. Anyways, there was a pig leg right above our heads at the bar. Eventually, it gets served I believe.
BLUES CLUES
Meghan was able to score me an invite at the most lively party happening in Chicago on Saturday night.
Snoop dog wasn’t there, and I didn’t get any photographs to prove it.
However, after the party, I did get some shots at the blues bar, Kingston Mines, that was the next stop that night. Quite the talent on the instruments.
DAWG CHECK
Well, before I get to the fun and exciting stuff, I’ll share this experience real quick!
Before heading out to meet friends to watch the Cleveland Browns game at John Barleycorn, a Cleveland themed Chicago bar, I had to extend my garage parking for my car. Rewind a bit, and this is exhibit A why having a car in the city may not always be the best option, or just don’t be a nincompoop such as I.
Long story short, two days prior on Friday, I parked in the wrong garage that I booked on the SpotHero app. However, the valet attendant didn’t even notice like how I hadn’t and still parked my car and gave me a ticket. We would come to discover this as I went to extend my parking at a garage that I didn’t initially book at. So, this resulted in me having to move my car to the correct garage across the street, and then I was a nincompoop there, too.
After an hour goes by, Meghan solved my problem, extended my parking, and we were off to John Barleycorn to meet Nicole.
“No big deal”
This Cleveland themed bar was lowkey rowdy for the Browns vs Cincinnati game. I’m told it gets more crowded than it was, and I was also told its closing in January and being turned into a dispensary. RIP Johnny Barleycorn and may you get higher than a 757.
We played some flip cup while watching the game. Check out my hilarious first attempt. I would try again later and go 2 for 3, but overall couldn’t secure the prize.
The Browns captured a W, and our group was off. I met Diehl’s dog and from that point forward, Meghan and I took a trip to the lake. As you can tell I don’t hold the camera much.
SHOW OFF
With a little time left before I start my trip back home to Cleveland, Meghan treated me to the ATM.
Not just any ATM, but a CUPCAKE ATM.
As always, I got two. The gluten-free blueberry and the vegan red velvet. I made sure to save them for my ride home. I’m not sure if I’ll share the photos of me eating them in this post yet, but if I do I apologize.
All in all, my first visit to Chicago was a huge success. It’s always fascinating to observe the differences in cities, lifestyles, and cultures outside of where I spend most of my time. I am truly grateful for the friends of mine that made all of it possible and who shared in the making of this post.
Boy meets world.
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