• Natchills


Okay, so Chicago aka Chi town aka the Windy City, what can I say? Thank you. Thank you for the amazing people, food, art exhibits, cocktails, desserts, coffee shops. Thank you for the beauty and the experience you gave me. Thank you for an absolutely amazing experience. Chicago is one of those cities that you never stop exploring no matter how long you’ve been there and I was lucky enough to get to know it during my six-day stay.

My friends and I initially went to Chicago for Complexcon and for those of you who don’t know what that is, Complexcon is a convention, held yearly, of Complex Magazines pop culture (I give an inside look on what that was like in another blog post).

Before I get started I do want to give a huge shout out to my friend Katrina for giving me the rundown on what things to do out in Chicago. Even though we couldn’t do it all the places she recommended and we visited were unbelievable so if you’re reading this post, thank you!

The most popular places to stay in Chicago are Streeterville, which is the center of absolutely everything and South Loop. We happened to experience both. If you need any Airbnb recommendations don’t hesitate to reach out! I’ll be more than happy to help. Now let’s get to the juicy stuff. Ladies and gents I’d like to introduce to you to Chicago.




Raised Rooftop

Since we arrived late afternoon we went to our hotel and got ready for the night. While getting ready we decided a rooftop would be appropriate. We decided on Raised Rooftop Bar and I highly recommend this place to anyone looking for amazing food, great cocktails and even better service. Not only does this place have the food, cocktails and service down pact but the view? I mean come on it’s Chicago, views for days!

Andy’s Jazz Club

To end the night right we decided a nightcap at Andy’s Jazz Club seemed appropriate. I absolutely love jazz so when going to places like this I’m a bit of a critic. There is a $10 charge to get into this place but worth every single penny. I love the respect that surrounded this place. The moment we walked in they advised us to keep our conversations to a minimum out of respect for the band and even a small detail like that changes the way you feel about a place. And of course the band was unbelievable and their great cocktails didn’t hurt either.


Wildberry Pancakes and Cafe

After getting some well deserved rest we were ready for what day two had in store for us. We were hungry and on a mission to get Wildberry Pancakes and Café since we’d heard amazing things. We decided to walk because we wanted to get to know the city but just a little tip for all my explorers:


Not only does it rain but for whatever reason we failed to remember we came to the windy city and that combo is no bueno my friends. After almost 40 minutes of walking in converse we finally got to our destination and wow! My mouth waters as I think about it. It’s safe to say

that the journey we took was well worth it.

The Bean

I’m sure we’ve all heard about the famous bean at Millennium Park. This was definitely something quite beautiful to see in person and worth the walk (it’s also across Wildberry Pancakes and Café). I would definitely recommend you stop by and take some memorable pictures.

Broken English Taco Pub

So finally the sun is shining and the heat was steering us into the direction of some drinks! A Chicago local we met was actually the person who recommended this place for happy hour and when a local recommends, you do! The décor of this place was unbelievable. The margaritas? Well, let’s just say we were four drinks in and left feelings extremely happy.

Emporium Arcade Bar

Ahh, barcades! The perfect combination of being an adult and bringing your inner kid out to play! This place was pretty cool because it had so many beer selections and games of course. The night we went they had a live hip-hop performance which I thought was amazing and brought ambience to the place. If you’re looking to go to Wicker Park let this be your starting point. Don’t forget to bring your inner kid along for the ride!



Another amazing breakfast/lunch place to go try is Yolk. They have several locations all over Chicago and is a very popular place (according to my sources). After the night before I needed something light and the avocado toast with smoked salmon didn’t disappoint. This place has everything you can think of including a side of mini pancakes for taste! What a treat it was to go to Yolk and indulge in all its deliciousness!

Museum of Contemporary Art of Chicago

Virgil Abloh: Figures of Speech

I think the collaboration that MCA and Virgil Abloh did was genius! For those of you who don’t know who Virgil Abloh is, he is a fashion designer and founder of his stand-alone brand Off-White and is also, amongst other things, an entrepreneur and artist. He’s also known to some as Kanye West’s best friend. I loved that this exhibition was curated to demonstrate Abloh’s creative career and interests such as music, fashion, architecture and design. This exhibition is only available until September 22, 2019 so if you’re in Chicago make sure you don’t miss it!

The Signature Room

After an afternoon of art, we thought a cocktail with views seemed appropriate. This gem is located on the 96th floor in Streeterville and yes, you guessed it, views on views on views. It feels like you’re on top of the world! And who doesn’t want to go to the 96th floor of a building and feel like this with a cocktail in hand?

Giordano’s Deep Dish Pizza

So we all know that Chicago is known for their deep dish pizza, right? I mean if you don’t, now you do. Rightfully so we had to get our hands on one of these and see what all the commotion was about. Giordano’s is one of the popular places for this deep dish pizza. If you go expect a long wait because of its popularity. The wait can be as long as an hour. The good thing is that since deep dish pizza does take so long to make you’re able to put in your order before getting seated and once you’re sat the order comes out fairly quick.

Okay, so here’s my personal opinion on deep dish. It’s really good and all but this isn’t pizza, it’s more like a casserole. I’m not sure why people compare NYC pizza to Chicago’s deep dish pizza because to me they are completely different things. A pizza is a slice with a topping and deep dish is layered. But hey, you be the judge of that and let me know what

you think.

Day four and five were dedicated to Complexcon. As mentioned at the beginning of my post, this was the primary reason for our travel to Chicago. This convention was held in McCormick Place and it’s a festival that brings together pop culture, music, food, innovation, activism, education and much more. I will briefly go over my experience but if you’re interested in possibly attending one and in learning more about what Complexcon is all about click on the link below to be directed to the in depth blog post about this event!



Complexcon Day 1

Day four aka day one of Complexcon was definitely one for the books! Here’s what we did:

Live show of Hot Ones w/ Sean Evans and Juice Wrld

Full Size Run with Brendan Dune, Matt Welty, Trinidad James and Allen Iverson

NBA 2k: How 2k is cultivating what’s next in culture with Don C, Karl Anthony Towns and Steve Stoute Fatpour Tap Works

I saw this place on our way to Complexcon and at first glance saw that it was a beer place which grabbed my attention right away. I must say that I did love all the different beer selections they had and the services was also great but the food? Not impressed. I like to be honest with you guys when it comes to recommendations because I hope that through my honesty I’ll gain your trust in future things I may recommend. The food was pretty much drenched in oil. I’m all about having oil in my food so it doesn’t have a dry taste but it was overwhelming. I did not enjoy my dish at all. If you’re looking to just have a beer this is definitely the place to do it.


Complexcon Day 2

Day five aka day two of Complexcon was as interesting as day one, here’s an overview of what was done:

Sneakers in Hip-hop with Don C., Wale and Allen Iverson

Live Comedy Show – Group Therapy with Nick Olge and Chris Redd

Take over the Block with Killer Mike, T.I and David Banner

Chicago Waffles

Breakfast was definitely served at Chicago Waffles! Naturally since its name had waffles in it I had to try one for myself and wow, amazing, delicious, unbelievable (oh and I’m not much of a waffle person either). I definitely recommend you head over to Chicago Waffles on one of the days you’re in Chicago to try these mouth watering delights!

Three Dots and a Dash


I think this was one of the coolest places I went to in Chicago. After walking around Complexcon all day we were starving and in need of delicious cocktails. This place can easily be missed because it’s down an alley but even the walk there was dope! With their creative cocktails, delicious food and unbelievable service it’s no wonder that people have such great reviews about this place. It’s intimate, fun and they play really cool music all night long. The décor of the place was beautiful but the presentation of all the drinks and food was out of this world! If there's one thing I want you to do during this stay if you can’t do any of the things I’ve listed is go to Three Dots and a Dash, you’ll be happy you did!


Here we are on our last day and because I knew Complexcon was going to take up an entire weekend I decided we should fly out Monday night instead and enjoy an extra day. Here’s what went down:

Burger Bar Chicago

Word around the block was that this burger joint was a must and so we did! It was amazing and the options were great in terms of variety and additions. Trying their wings is also a must, their sauce game is on point! If you’re in the mood for beers, they also have a grand selection to pick from and the service? Let’s just say we left pretty happy.

Art Institute of Chicago

Another day, another art gallery! Everyone said this was a place to see and they weren’t wrong. Located in Chicago’s Grant Park this art institute is known as the oldest and largest art museum in the United States and clearly we couldn’t miss the opportunity to see what it was all about. I advise that you go with ample time as there is a lot to see and discover in this place. There is a peaceful aura that you get once you start looking at all the art. You feel as if you’re living in all these eras yourself. Go check it out if you have time, it’s definitely worth the $25 entrance fee.

Hero Coffee Bar

Coffee shop + alley’s = YES. I discovered this little place passing by before our drop off to a restaurant. I walked back and well, you see the picture, right? How can you not go visit! This coffee shop is located in a little alley with outdoor seating was a dream come true for a nerd like me. I’m happy to report that the coffee was just as good as the location.

Gordo’s Homemade Ice Cream Bar

To finish off the trip I needed to try some dessert since I went all week without having any! Gordo’s Homemade Ice Cream Bar will make all your ice cream bar dreams come true. You go in, pick an ice cream bar flavor and they lather it in whatever you can possibly think of. My choice was strawberry with fruity pebbles and just one word, wow!


Although six days seems like a long time, like I said before, you never stop exploring Chicago no matter how long you’ve been there. Here are a few places I sadly missed but would recommend you visit:

Lagunitas Brewing Company

Goose Island Beer Company

Drinks at Navy Pier

Willis Tower Skyscraper

Joy Rooftop Bar

Little Toasted Whisky Bar

La Pasadita Tacos

London House Rooftop Bar

Bombo Bar

I hope that by reading this post it gives you a nice insight on what Chicago is all about. I would love to hear that you went to some of these places and had the experiences I did, if not better. And again, thank you Chicago, experiencing you was a gift that I’ll take with me forever.

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© 2019 by Eynar Ledezma, P.O. Box 5205,Englewood,NJ 07631