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Chicago Trip + Recap 2024

I just got back from Chicago and had SO much fun. For those of you that may not know, my husband, Andrew, goes to Chicago for work twice a year. I like to tag along for at least one! My first time going to Chicago was last year and had a blast, so we knew I had to come out again this year. While Andrew is working and doing his thang all day, I hang out with the other wives that come and/or shop around and explore the city. There are so many great restaurants and shopping, so in case you are wanting to visit, here is a little trip recap from 2024.

My beautiful new baby that came home with me

Where We Stayed

This trip, we stayed at Hotel Chicago which is a super convenient and nice hotel right by the river walk. I felt safe the whole time walking by myself. Hotel staff were super friendly and hospitable, too. No free wifi, but if you go to the front desk and ask for wifi, they will give you a code that grants you free access! This hotel is again, right by the river and across the street from the Trump Tower and several great restaurants, making it a great spot for those on the go. This hotel also has a breakfast spot located inside the hotel! The hotel lobby bar was great and again, convenient.

Favorite Restaurants this trip:

Beatnik on the River: Super trendy spot we found on Instagram. If you want a brunch spot that is super cutesy, this place is great! The food was decent in my opinion, and they didn’t offer any accommodations/off menu items. I asked for just a side of scrambled eggs and they gave me a hard time about it. Kind of odd. Great spot for mimosas, though!

Shaw’s: We always try to go here at least once while here. Shaw’s is an iconic spot! GREAT seafood and, really everything is good. I had gooood sushi for the first time, and now I am a sushi gal. Who knew?! Great cosmopolitans, too!

Ralph Lauren Restaurant: Again, an iconic Chicago spot! Super hard to get a reservation. Spots open up one month out from your desired date, and I would call the restaurant right when they open to reserve your spot. Beautifully charming on the inside with amazing service. I had an old fashioned and it was super delightful! The interior design truly looks like out of a Ralph Lauren magazine!

Barrio: An upscale mexican restaurant walking distance from the hotel! I went for brunch and low key, the tacos and guacamole were so freaking good! Great mimosas, too!

Tiny Tapp Cafe: Right on the river walk, walking distance from everything! We love their coffee in the mornings. During the nighttime, this cafe turns into a bar! Super cool and again, beautiful location. I think I went there every day for coffee!

My Adventures:

Chicago Trips are always fun, but also super unique for me. I tag along on Andrew’s work trips, so I am mainly on my own the whole time. Because of this, my main itinerary for the day is shopping! I just like to walk to all the hot spots and window shop….and sometimes proceed to checkout. I got my STUNNING hot pink Dior Saddle Bag… something I did not plan on but also had my eyes on for a long while. It is such a chic bag and truly the best pink for me! This bag really made the trip even more memorable. So thankful for such a moment!

I haven’t tried any museums yet, mainly because the last two times I went I have been loving the shopping. I think if I go again, I will hit up some history!

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