Summertime Chi.
I heard through the grapevine that the weather and vibes had a grown and sexy feel—so you know I had to check it out. If you are new around here, I do not believe in gatekeeping, so I will be sharing all the deets with you all! Here’s how my birthday weekend went down in the one and only Chicago, where we sipped, danced, and ate our way through the Windy City. Grab a drink and let’s dive into the fun!
First things first, we touched down at O’Hare Airport and hopped into a Lyft (a bit janky, but we made it safely—story for another day!) straight to our hotel, theWit, nestled right in the heart of downtown Chicago. Location is everything, and theWit nailed it with its chic, modern vibes, putting us right in the middle of all the city’s action. And let me tell you, the view from our room was absolutely spectacular! We had floor-to-ceiling windows that offered stunning views of the city from every angle. If you’re planning a stay, I highly recommend booking a room ending in 01—those are the corner rooms with the best views. (See, I told you I don’t gatekeep 😉) See views from room #1801 below!
After we settled in, we walked over to Pizzeria Portofino, which sits right on the river, and enjoyed cocktails, pizza, and pasta. If you know me, you know that eating out at the best restaurants is my thing. We thoroughly enjoyed the food and the view from the balcony—it was the perfect spot to kick off our trip!
Pizzeria Portofino
I loved the Italian Sausage & Fennel pizza, along with the Charred Pepperoni pizza (we went half-and-half on that one!). Oh, and the Spaghetti Marinara? Totally hit the spot!
After a much-needed nap, we decided to take a walk and explore the beautiful city. We stumbled upon The Dearborn, a New American restaurant, and were thrilled to find the service, food, and cocktails were a solid 10/10. The Dearborn ended up being my favorite restaurant we tried while in Chi!
The Dearborn
highly recommend any of the cocktails—they're all amazing! For starters, the Midwest Fried Chicken and the Peruvian-Style Ceviche are a must-try (OMG, so good!).
After dinner, we wandered around for a bit and eventually made our way back to our hotel lounge—ROOF on theWit. The vibes were awesome, and the DJ was on point! My man and I danced until we couldn't anymore—such a perfect end to Day 1.
ROOF on theWit
After a quick dinner, I hit the hotel lounge, ROOF on theWit, and honestly, it did what it needed to do! I believe Fridays and Sundays are hip-hop nights, and the vibe was on point. I also loved how diverse the crowd was!
Day 2 was absolutely awesome! We found ourselves feeling a bit hungry before our planned brunch, so we decided to grab a quick bite at Goddess and the Baker—and wow, what a treat. Even on a busy Saturday, the service was spectacular. We did have to wait in line, but it moved surprisingly fast. Please be prepared for great food in Chi!
Goddess and the Baker
I highly recommend the turkey bacon and egg croissant, paired with the iced lavender vanilla latte!
After grabbing a bite at Goddess and the Baker, we got ready for brunch at Terrace 16. The views were breathtaking, and the mimosas were unlike anything I’ve ever had. However, the food was a bit mid, so I'd recommend eating somewhere else first and then heading over to Terrace 16 for cocktails and mimosas—which, honestly, had us LIT. lol
Terrace 16
As you can see, the views were spectacular! But trust me, before you head over, make sure to eat something good first, then come to enjoy the cocktails!
After a fabulous brunch, we decided to take a little break to recharge for the evening ahead. Once we were back in action, we kicked off the night with dinner at Costera Cocina Tulum. This place is like Tulum but make it upscale—think chic, tropical decor with a touch of luxury. The ambiance was everything, and the food took us on a flavor trip. I savored some flavorful short rib and perfectly seasoned tacos, and the cocktails were to die for. It was the perfect blend of laid-back yet luxe, setting just the right tone for the night.
Costera Cocina Tulum
I highly recommend the Salmon a la Plancha, which was cooked to perfection, and the Braised Short Rib Barbacoa, which was tender and bursting with flavor. And don’t even get me started on the cocktails—each one was a masterpiece.
Masada
But we weren't done yet! After soaking up the vibes at Costera, it was time to turn up at an Afrobeats spot called Masada—and let me tell you, this place was a whole vibe! The second we stepped in, the energy was electric. The music was popping, the beats were fire, and the crowd was ready to dance. The DJ was on point, dropping banger after banger, and we couldn’t help but get caught up in the rhythm.
Now, on to Day 3! We started the day slow, enjoying a restful morning before exploring a bit. By the afternoon, we were ready for more adventures, so we hopped on a water taxi to Chinatown—such a fun way to see the city from a different angle! Once we arrived, we treated ourselves to some delicious dragon fruit boba tea from Joy Yee (it was SO refreshing) and then dug into some authentic Chinese cuisine at MCCB.
Chinatown, Chigago
Our first stop was Joy Yee for some refreshing dragon fruit boba tea—perfect for cooling down. We then strolled through the bustling streets, soaking up the vibrant atmosphere. For lunch, we hit up MCCB (Modern Chinese Cook Book) for some delicious authentic Chinese cuisine. Be ready for a bit of a wait—it’s a popular spot! But trust me, it’s worth it!
As you can tell, Chicago is a whole vibe when it comes to the food scene, and y'all know I love myself a good meal! After doing my homework, I picked Alla Vita for dinner, and let me tell you—it did not disappoint. The ambiance was on point, the pasta was pure perfection, and the drinks? Oh, they did what needed to be done!
Alla Vita
I highly recommend the tagliatelle pasta and definitely the espresso martini (with tequila, of course!).
After dinner, we didn’t really have a plan, but my best friend (shout out to Amari!) found this vibey spot called Moneygun. We enjoyed some cocktails, danced a little, and just soaked in the good vibes as we geared up for the next day!
Moneygun
Moneygun was hella packed when we got there! I don’t know all the details, but I’d definitely recommend getting there early on a Sunday if you want to snag a table or a spot near the bar. This place is a whole mood for a night run!
Day 4 was all about chill vibes, honestly. We grabbed lunch at Mercadito, and it was pretty good! I had the shrimp ceviche and some delicious al pastor tacos with pineapple, while my man went for the torta de brisket. The margarita and paloma were a hit, and to top it all off, they even gave me birthday shots! It was such a fun little surprise that made the day even more special.
Mercadito
I highly recommend the Chile de Árbol salsa! It was spicy, but the complex flavors made it incredibly enjoyable.
To wind down the day, we took an architecture boat tour with Wendella Boats in the evening. I love discovering what makes a city unique, and we thoroughly enjoyed the informative guide—and the cocktails didn’t hurt either!
On Day 5, as we prepared to head out, we just had to make one more stop at Dearborn because it was that good! I went for the fish and chips this time—fun fact: the chef at Dearborn actually beat Bobby Flay with this dish! After an early lunch, we headed back to the hotel to grab our bags. The manager suggested we take the Blue Line train to the airport, and since my boyfriend and I had never ridden a train before, we decided to try something new!
Dearborn Part 2!
Honestly, the service alone would make me fly back just to eat at Dearborn. The food is fresh, tasty, and totally worth it. I highly recommend checking it out!
And just like that, our Chicago adventure came to an end. From the vibrant food scene to the stunning architecture, and the endless vibes at every corner, "Summertime Chi" truly lived up to its name. This city has so much to offer, and I’m so glad I got to celebrate my birthday here with my favorite people. If you’re looking for a destination that’s full of life, flavor, and unforgettable moments, Chicago is the place to be.
Until next time, Chicago. You’ve been amazing. Cheers to new adventures and more memories to come!
