Sabrine in Chicago! This past May I had the opportunity to visit Chicago during a business trip over Cinco de Mayo weekend! Continue reading for the 48 hour recap of my fun weekend in the windy city!

Saturday, May 4th - Arrival in Chicago

I was so excited to be in Chicago for the first time this past spring during a quick business trip! 

This was not my first trip to a new city this year… I actually went to Miami for the first time during the first weekend of February, also for a weekend business trip, but didn’t have any time to do any sightseeing since I was working both Saturday & Sunday. 

This time, however, I knew I would be in Chicago for about 48 hours and only working on Sunday, so I was excited to be able to explore the city a little bit. 

As mentioned, the event for my client was on Sunday, and they booked my flight for the day before, to ensure that I would be in Chicago the day of the event with no delays. This meant that Saturday afternoon/evening was free and room enough to sightsee for a few hours before needing to get my rest for the event the next day. So I decided that I would try and squeeze in a mini photoshoot and some sightseeing on Saturday. I figured I could arrive, check in to the hotel get ready, take some pictures, and then have dinner and call it a night. And that’s pretty much exactly what I did!

After a short plane ride from the west coast to Chicago, I landed at Chicago Midway International (MDW) airport. Oddly enough, I did not fly into Chicago O’Hare, which I thought was the main airport. Apparently the airport I arrived at was actually cheaper and more central to the downtown area. Shocking, I know.

Once I was off the plane, I called a Lyft to take me to my hotel. I usually like a quiet ride, but when I’m in a new city, I find that asking the locals where to eat is the best bet rather than trying to Yelp something or find it on your own. The driver was actually very happy to offer suggestions on where to eat after I told him that this was my first time in Chicago.

I ended up sharing a Lyft with another person who got dropped off before me, but again I didn’t mind the extra stop this time because I enjoyed being able to see more of a new city. After dropping them off we headed to my hotel and I got a great view of the “Miracle Mile” downtown buildings and the Chicago Riverwalk as we drove by.

Finally I arrived at my hotel, Aloft, which was centrally located in the downtown River North district. My hotel had a very urban chic, young, tech-friendly vibe. As soon as I walked in the door I could smell this wonderful lemon fragrance that reminded me of lemonade. To the left of the entrance they have a really cool looking restaurant, and to the right of the entrance is a lounge area that had a good amount of tables and chairs, newspapers, and games for guests to play. The check in desk was located in the middle of the lobby at a circular desk that reminded me of a high tech “help desk”. After I checked in, I went up to my room and began getting ready for my mini photo shoot. My room had a nice double bed with a decent bathroom area. The hotel had blueberry Bliss products for toiletries that matched the hotel’s blue color scheme. There was also a desk that I used to set up my laptop and camera equipment to charge.

Before I even left home, I checked Instagram for some local Chicago photographers. I figured since I was going to be alone on this trip I might as well hire someone to take some pictures of me while I explore Chicago cityscapes. This also is a great tip for traveling because local photographers know where to go in the area – if you are interested in sightseeing while you are taking pictures, definitely ask a local photographer for recommendations!! I found a great local photographer named Emily and told her where I was staying and that I wanted to get some classic Chicago backgrounds in my pictures. We met up at my hotel and shot some pictures in the lobby and outside patio area before we walked along the streets downtown, over the Riverwalk, and all the way to the Chicago theater. The shoot lasted about an hour and I had a great time walking the city with her. I definitely would recommend her to anyone in the Chicago area! Check out her Instagram here and some of my favorites from our shoot below! 

After the photoshoot, we parted ways at the Chicago theater. I was about 2 miles away from my hotel but didn’t feel like getting a Lyft back because I wanted to explore more of the city now that my session was over. 

I happily walked down the streets of Chicago in my Sam Edelman heels until a few blocks later when I realized I was the only one wearing high heels. Everyone was walking in sneakers or thick platform heeled boots, not a skinny strappy sandal like I was wearing. That was the first time I truly felt like a “tourist” in the city.

As I walked towards my hotel I realized my best bet would probably be to change into some sneakers also and head back out to explore. I quickly changed out of my heels and into my comfy Nike sneakers and switched my blazer for my new favorite jean jacket. I felt tons more comfortable and ready to hit the town.

By this time the sun was setting and it was about to be dinner time soon. While there was many restaurants near my hotel, I really enjoyed the Riverwalk area and wanted to try and find a restaurant with a good view. For those of you who aren’t familiar with Chicago/the Riverwalk, basically there is a river that runs directly through downtown Chicago (the Chicago River), and many bridges that cross over it to connect one side of the city to the other. If you’ve seen Never Been Kissed or My Best Friend’s Wedding, then you’ve seen the infamous Chicago Riverwalk and the tour boats that go by every few minutes (it seems like). If you’ve never been AND never seen those movies, the Riverwalk looks similar to San Antonio’s riverwalk (although I’ve never been there) but basically just picture a river with restaurants on either side and areas to walk and watch the boats passing. 

Anyways, so I finally walked back over there again and made my way down the stairs to the actual Riverwalk area rather than just the actual bridges, where they had some restaurants and a nice looking wine bar. Across the river from where I was on the other side of the Riverwalk was Dick’s Last Resort, and I realized that I was probably going to end up paying premium prices to eat on the Riverwalk. 

I decided to have a drink at the wine bar while I chose which restaurant to go to. By the time I was there the sun had gone mostly down and the crowd started to pick up. I stood in line in a tented bar area while looking for a seat outside in the open air area. When I got up to the bar I ordered a Rose. To my slight surprise, the wine was $14 for one glass! I knew it was going to be on the pricey side, but $14 for one glass was pretty ridiculous. BUT, I had already waited in line and ordered the drink, so I paid for it and took my seat to enjoy the view and my $14 wine. (Very touristy MOM-like photos below and one photobomb, can you spot it?)

After finishing the wine, and a good amount of people and boat watching, I decided to head back towards my hotel. I remembered that my Lyft driver told me that I needed to eat at Portillo’s while in Chicago, so I looked up the closest one and was glad to find one that was within walking distance from my hotel.

Portillo’s is a Chicago staple. I had never heard of it until the Lyft driver told me about it, but this place is FAMOUS. There was signed pictures from celebrities all over the walls! I thought Chicago was most known for it’s hot dogs, but turns out the local favorite in Chicago is not a hot dog, but a sandwich that is simply called “Italian Beef” (sandwich), and everyone knows what you are talking about. Don’t believe me? I took a picture of Guy Fieri’s signed picture (below). LOL

I’ll admit I was skeptical at first, so I ordered a classic Chicago dog in addition to the Italian Beef sandwich just in case I wasn’t impressed. To my surprise, the hot dog was just okay, but the Italian Beef sandwich was DELICIOUS.

To those who are still wondering what an Italian Beef sandwich is, let me break it down for you. The sandwich is basically a french dip but with thinly sliced “Italian Beef” and already dipped in “gravy” they call it but basically their “au jus”. So its not soggy but it’s “wet” and comes with hot peppers (my favorite) on top! You can ask for it “dry” which means not dipped in gravy and also without the hot peppers if needed. I got all my food to go and ended up eating it in my hotel room for privacy and because it was getting pretty late. I also wanted to film a video of me eating the Portillo’s for a true reaction video and didn’t want anyone watching me, lol. Video coming soon??

Not gonna lie, Portillo’s was so good I ended up going there AGAIN the next day. I could’ve easily went anywhere else or a more expensive restaurant but they had such a large menu and they were so delicious I decided to go back the next night and try something else from the menu even though I really just wanted another Italian Beef. 

Sunday, May 5th - Day of Client Event

Sunday was the day of my client’s event. I was hired at the end of last year to plan a multi-city international meet & greet tour for Aunt Jackie’s Curls and Coils. We already completed the first stop in Miami in February, and now this was the second stop, in Chicago.

My job as project manager/event coordinator is to handle all aspects of the event. This includes finding the venue, choosing all vendors, hiring any influencers/bloggers, and making sure all logistics of the event are taken care of. Most of the work happens months prior to the event, and then the day of I am there to ensure everything runs smoothly. 

This event started in the early afternoon, so I was able to sleep in and take my time to get ready prior to heading to the venue. We ended up using another salon for this stop like in Miami, named Huetiful.

The salon was in the south Chicago neighborhood and was really nice inside. They had a separate entrance to the area where we set up our  that was separate from the salon chairs/wash area. The event itself lasted about 3 hours and we had appetizers, cocktails, music, local Chicago natural hair influencer @westafricanbaby, product giveaways, and a live wash & go demo using all Aunt Jackie’s products. You can take a further look into the event by reading the blog post by local Chicago beauty & natural hair blogger @beautyandthekinks and you can check out some of the photos I took from the event below. 

After the event, I took a Lyft back home and went back to Portillo’s. This time I ordered their hamburger and was not disappointed. If you know me, you know I love a good burger, and if it wasn’t good, I would definitely tell you. I didn’t end up going out for Cinco de Mayo but I walked the streets by my hotel to and from Portillo’s and got to see the crowds of partygoers. I felt happy that I was going back to my room to eat my food in peace.

Monday, May 6th - Chicago Departure

My final day in Chicago was a quick one: woke up late morning and got ready for my flight home. Checked out and caught a Lyft from the hotel to the MDW airport for my flight back home.


Things I didn’t get to see in Chicago that I would love to see/do next time:

  1. The BEAN! 
  2. Chicago Art Museum
  3. Inside the Chicago Theater 
  4. An actual boat cruising down the river 
  5. A good pizza place
  6. This cool looking park we drove by on the way to the event… I want to say Memorial or Millennium park? Will look into this.. 


Last thoughts:

Chicago was fun! Even though I was only there for a quick work trip, I was happy to see part of Chicago and enjoy the cool city views! And Portillo’s is definitely a highlight and a must-go!

Have you ever been to Chicago??

What or where did you enjoy the most?

Thanks for reading!

Talk soon,

XO, Sabrine