Chicago is home to some of the most recognized rappers, and singers in the game.  R. Kelly, Twista, Common, and Da Brat to name a few.  But it’s also home for some cool activities and great food.

Where We Stayed

Our hotel of choice was the Wyndham Chicago Riverfront. It’s location was great, and was up on East Upper Wacker and the rooms were pretty decent. It’s about a mile from Millennium Park and in my opinion it’s walking distance to some nice restaurants and just about everything except the Sky Deck. But I will talk about the Sky Deck later in this post. But please keep in mind, it is directly in front of the Trump hotel…..

What We Ate



Everyone knows that Chicago is the home of the deep dish pizza and I totally understand why! Because I was super pressed to go, I did lots of research and was told to try the pizza spot Giordano’s on Van Buren. The location was right off of a major road way and the service was ok. Now lets talk about the PIZZA! I ordered a really simple personal pepperoni and cheese deep dish pizza and it was good. Was it slap your momma good? Naw, the deep dish was too bready for me, and I am not a big fan of crispy crumbly pizza. However, I wanted to give it a try and check it off of my bucket list.




Now what I will rave about is the burgers from Portillo’s up on W Ontario. I absolutely loved the fact that it was walking distance from the hotel. Maybe a 10 minute walk.




What I also loved about the spot was how it gave a sportsy vibe, and it had a little hustle and bustle. They have more than one register meaning they will have more than one line to place your order. Since the spot is pretty poppin’ they also have seating outdoors and upstairs. Now about the food…..

I had a pretty simple cheeseburger with mayo, lettuce, ketchup, pickles and mustard. You know, something simple so the wouldn’t mess it up. And man oh man I really enjoyed it. It’s a pretty nice size sandwich. The burger has a nice sandy bun, and the meat has a flame broiled taste. Everything was fresh and their small crinkle fries were perfect! It was so good yall I went twice. (Don’t judge me)


Just about everyone has heard of Chicago’s legendary “Garret’s Popcorn” and I call it legendary for a reason. I call it legendary because I smashed an entire tin of it in no time because it was just that good! There are many Garret’s Popcorn locations around the city so don’t trip if you’re running low on time to snag some for yourself. Try the “Garret Mix” if your looking for a salty and sweet combination. It’s real cheddar cheese and sweet, buttery caramel will definitely be a treat and you won’t regret it. If that’s not your speed, here is the link to check out some of their other popcorn.

What To Do

While in the Windy City, it was only right that we checked out the “Sky Deck” at the Willis Tower. Tickets were about $25.00 each and you can take an elevator about 105 floors up. Now don’t get it twisted, all is well and cool until you walk up on that clear box and you can see God’s green earth beneath you. Lol I was so chicken I had to crawl into the box, psychologically  my brain said “girl don’t you walk into that glass box, crawl instead” Lol It was most definitely interesting experience and I highly recommend doing this activity with some of the homies that can capture some dope pics.



Millennium Park

After grabbing our popcorn, we walked about a mile to Millennium Park. It’s South of Michigan Ave and is the home of the “Bean.” You know the huge silver thing ? Well while in the park we realized that there was an event going on called the “Young Artist Showcase” or YAS Fest. The vibe was everything and the temperature was just as on point.


In conclusion, Chicago is most definitely an awesome place to visit. Be sure to check out where Michelle Obama went to High School and the Obama home as well. Remember to bring a jacket because this place is truly the windy city. All in all, I had a great time and Chicago treated me well.

Until next time!

%d bloggers like this: