My First Time in Chicago

By Posted on 0 Comments 8 min read 842 views

I’ll be visiting Chicago again soon!

The past few days since Tuesday, I traveled to Chicago for the first time ever. It was an amazing experience going west for the first time even if it were just a short 5-6 hour trip there. We stayed at the Hyatt Regency McCormick  Place minutes away from downtown Chicago. They had excellent room service and great views. From the minute we walked in, we experienced nothing but the best customer service.

The room has a large bathroom with two showers heads (one hand-held and one regular) and a seat to sit and shower in (assumably for the elderly or disabled). With a large window to enjoy the views of the city’s skyline, the curtains also drown out sunlight perfectly for those looking to sleep in.

We stayed for two nights and a day and a half. The first night, we explored a bit of the city and headed straight to The Laugh Factory, home of some of the biggest comedians today. The beginning acts were okay but towards the end, I couldn’t have had a better time. I couldn’t hear all of the names of some of my favorite comedians who performed that night which makes me so sad, but I did manage to grab one: Vincent Bryant. There’s a two drink minimum but the drinks are super affordable. Overall, I had a great time.

Our next stop was for food and we decided to eat at The Delta which I found on Yelp. The decor is beautiful. We were greeted by young men in casual clothing with immense politeness. We ordered our food as I got the traditional burger (because I’m a burger enthusiast now lol) and my friend got the fried chicken. The burger was dry-aged beef patties, American cheese, onions, pickles, D.A.F. sauce, and fries. The fried chicken, however, was the real delight. It surprised me because it was one of those fancy fried chickens which usually can be a hit or miss. The fried chicken consisted of black garlic, sweet relish, hot sauce, and came on white bread. It sounds super simple but it was the most delicious fancy fried chicken I’ve ever had in my life. As we were waiting, we noticed the decor. There were cotton (mirroring those slaves picked nearly 300 years ago) and old pictures of Native Americans and black people all over the walls. There’s a weird thing they have for tamales throughout the restaurant as well. After speaking with the restaurant manager, he clarified that the Delta is an ode to the Mississippi Delta region. My experience with the restaurant was superb. The restaurant is black-owned which makes all the sense. It was a pleasure to see such amazing, and I mean amazing customer service from black folks in an establishment owned by more black folks. Young black men in the corners battle rapping but also attentive to the guests and super polite when it was time to engage. It was the most enthralling and happiest thing I’ve ever seen from a fully black establishment of people being themselves while simultaneously engaging with guests respectfully and timely without us ever having to wait or want for a thing. Way to break negative predominantly black-owned stereotypes. I’ll definitely return as my first stop the next time I’m back in town. I didn’t get any pics because I didn’t expect to fall in love with the restaurant nor did I plan to bring my camera with me for this first restaurant we visited but you can check out The Delta here.

Day II

We awoke early at about 7 and headed out to hit the city around 9 am. I love Chicago so much because things close at 4 am and are open again as early as 7. The first stop we made was to Millennium Park to see the Bean, so they nickname it.[/dropbcap]

After perusing Millennium Park and enjoying the awe, we headed for breakfast. Our first idea was to stop in at Cindy’s for brunch which had an amazing view of Chicago’s daytime skyline, Lake Michigan, and Millennium Park. We didn’t stay however because they only serve brunch on the weekends so we headed downstairs (in the Chicago Athletic Club) to the Cherry Circle Room because I really had a taste for eggs. I ordered the Van Doozer which consists of 2 eggs made any way you want (with exception of an omelet) 2 pieces of toast, 2 pieces of bacon, and 2 hash browns. I substituted the hash browns for extra bacon. My friend order the Triple Cheeseburger that came with fries. The Van Doozer was okay as I had 2 fried eggs, the bacon was a little too crisp, the toast was interestingly different. The burger, however, was delicious AF. It totally caught me by surprise. There were pickles, onions, tomatoes, lettuce, and dijon mustard. The burger patty was thick and juicier than I’d ever remembered having before. It was surely delightful. If I come back to the Cherry Circle Room, the burger is definitely a must.

After eating, we perused the city. We wandered around Michigan Ave and State St, hobbled into the stores to visit Chicago’s version of Zara (which was amazing and absolutely unfair how much more stuff they have than Detroit), and even came across Akira in person which I didn’t know they had any storefront let alone over 30 in Chicago alone. We strolled over to Chinatown which also had us in awe because it’s amazing to see real communities owning real full functioning neighborhoods. We even came across a K-Pop store in Chicago which was a bit ironic lol.

Later in the evening, we headed out for dinner and to absorb the night’s festivities as our last full night and only full day in Chicago – it was a short business trip. We asked around for the most “Chicago-like place to eat and we were told Miller’s Pub on Wabash Ave. We went and were greeted with amazing hosts. We were escorted to our seats. Our waiter was fantabulous and awkwardly funny. I mean seriously, the people in Chicago are some of the most interesting I’ve met in a short amount of time and seem genuinely friendly. We ordered our food. I had the Caesar salad with chicken, hold the croutons, and a glass of wine. My friend had the ribs which came with fries and coleslaw. We got out food…we were slightly disappointed. First and foremost, it’s a Caesar salad. It can be super amazing or super basic. But never have I had a bad Caesar salad except for that one time I realized the lettuce was Kale (because I despise Kale) and even then, aside from the vile taste of Kale, the salad still tasted decent. My salad had pieces of bacon in it which I found weird, half a boiled egg, and some small round green balls  (smaller than peas) which till this moment I couldn’t figure out what they were, so I ate around them. Let’s presume I didn’t order chicken, if I were vegan or vegetarian, I’d be certainly pissed. The menu didn’t notate anywhere about the bacon bits (which I didn’t think were real bacon, just bits which is gross) and egg being in my salad. I figured the only unwanted thing I’d have to worry about would be croutons but apparently not. I wouldn’t complain if the salad altogether tased good but it didn’t so I ate the chicken and downed my glass of wine, calling it a night on food lol. My friend had the ribs and to him, he felt it was solidly ok. The sauce wasn’t all that and the fries were little to crisp as if they left it frying a little too long. Neither of eating coleslaw because, why? So that was that.

We ended up at Kingston Mines which was a Chicago Blues Center. Filled with hella white folks and lots of soul, the vibe was surprisingly incredible. You walk in, you find yourself a seat, and you enjoy the entertainment. It’s fantabulous. It’s like a large hole in the wall with great energy. When one band is finished performing, everyone gets up and walks into the other room where you’ll find another stage setting for another performance from another band. The keyboard playing was going TF in. It was Wednesday night in Chicago and I was tired by 11:30, I won’t lie, however, I stayed for another hour in awe. When the second band was finished playing, they had the audacity to say there were 3 more hours of partying going down. It’s Wednesday night and entertainment is going down until 4 am. It was past midnight at this point. I could not believe what a real city can do. I didn’t get any pictures but again.


The next morning, we headed over to the Chicago Digital Summit and then we grabbed brunch before our final goodbye back to Detroit. We decided to give Cindy’s another go because although the first time around we passed, it was because I severely craved eggs and not just a regular meal. When we got there, we decided to order the steak option and split it in half. We ordered the Prime Skirt Steak which came with bean puree, roasted peppers, radish, topped with Cindy’s steak sauce. It was $27. I ordered a glass of wine which was $14. The wait was really long and we didn’t anticipate it taking so long as our next step was straight to the bus station (we took the Mega bus because it was extremely cheap – $20 roundtrip). After waiting a ridiculous amount of time for our meal, they set the plate down and I was upset. The plate literally consisted of six small strips of meat probably no longer than a finger and a half, about one inch wide. Why it took so long for 6- 8 small pieces of steak filled with flowers and peppers? We’ll never know but we ate it anyway. It didn’t, in fact, taste delicious and was probably the most tender steak I’ve ever had. I ordered it medium-well. Would I come back there again? I’m not sure. The ambiance is beautiful, the view to the city and Millennium Park, just striking, the food, not so bad. The wait, not worth it, and the prices for the amount of food? I could probably pass. If I do decide to come back, of course, I’ll be looking to Yelp to compare what I’m ordering because I don’t mind paying $30 for food if I can assure myself, I’ll leave full. We left still hungry and ended up at Chipotle and Dunkin’ Donuts shortly after.


When visiting Chicago, you absolutely have to go to The Delta. It’s located on North Ave and has some of the best hospitality you can ever ask for. The Fried Chicken is A MUST!

The Cherry Circle is cool too and I’d definitely try out that burger if you’re looking for a good burger in Chicago.

Kingston Mines is excellent for a Chicago authentic experience to the blues and leaves you with electrifying energy and new friends, for sure.

Millennium Park, duh! You can’t visit Chicago without heading to see the Bean. I don’t care how touristy it seems, just do it! It’s not as bad as visiting Times Square in New York, I promise.

If you’re looking for a hotel, the Hyatt Regency McCormick is an excellent recommendation I’d give. I’m picky about rooms especially bathrooms and their shower is great, excellent water pressure, has a handheld showered (which for anyone who knows me, I always travel with my own handheld showered to use at places I’m vacationing), and the view is beautiful.

I’ll be visiting Chicago again soon to continue networking and meeting new people so this will not be the last of my travels west soon. I hope this gave you some insight for those who’ve never been and for those who have but haven’t visited these places. Let me know if you go and comment below what you think if you ever hit up any of the above-mentioned places. There you have it, Chicago from my eyes, enjoy!


Subscribe so you don’t miss a post

Sign up with your email address to receive news and updates!

What do you think?

No Comments Yet.

Sign up to receive exclusive content updates, fashion, blogging/coaching services, & more!

Brome Sets The Bar
My First Time in Chicago