24 Hours in Chicago, Illinois

Ever since I went to Chicago on a Spring Break trip in high school, I had wanted to visit again as an adult. Luckily, that opportunity to visit Chicago again came up when I went to visit my best friend Lindsay in Indianapolis, Indiana (here) and we decided to do a night in the Windy City before I headed back to the East Coast in August 2023! While in Chicago, we did alllll-things Barbie-themed, from going to the Malibu Barbie Popup Cafe to drinks at Hampton Social to the literal best ever espresso martinis that I’ve ever had at the Starbucks Reserve Roastery and a few things in between. During my time in Chicago, I truly fell in love with the city all over again and I cannot wait to go back and visit Chi Chi in the future!

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Getting There:

Lindsay and I drove from Indianapolis to Chicago, since it is under 4 hours each way and I totally give props to Lindsay for driving us the entire way as I am NOT a city driver (confession!). I ended up flying home out of Chicago O’Hare airport on a United Airlines (my preferred airline!) flight back to Washington, DC. I was able to somehow get a flight into Ronald Reagan National Airport (DCA) from O’Hare which is RARE for United given that Washington, DC’s Dulles International Airport is a United Airlines hub. BIG WIN! Overall, I found navigating O’Hare to be pretty easy, as the airport is extremely nice and pretty fun with all of its displays, too.

Where We Stayed:

I am a big Hilton fan and a Hilton Honors (rewards) member! SO, we stayed at a Hilton with close proximity to the Magnificent Mile and the iconic Chicago Riverwalk. Our room had a beautiful view of the Chicago skyline, which was amazing especially after sundown. Personally, I LOVED where we stayed, as it was super close to everything in Chicago, allowing us to walk pretty much everywhere (with the exception of the Malibu Barbie Popup Cafe in a different part of town!). And, well, I LOVE a nice Hilton hotel, too!

What We Did:

Being transparent here, A LOT of our activities during our brief Chicago stay revolved around *none other than* … food and cocktails. Initially, we had planned to take an Architecture River Tour, however, due to the rainy weather, we decided against it – next time though! However, we did have a few fun activities during our time that didn’t involve food.

One of my favorite activities while we were in Chicago was getting to walk around after our night cap at Hampton Social alongside the Chicago Riverwalk, as the rain started to subside. Lindsay knows Chicago pretty well, so she was able to give me a free and fun nighttime skyline walking tour of the city. I LOVED getting to see Chicago’s skyline at night (there is something simply SOOOO magical about city skylines at night – am I right?!) and truly see the stunning city’s flair on a peaceful and partially drizzly Monday night. We walked across the bridges alongside the Riverwalk and admired all aspects of the city skyline. We also saw one of Chicago’s well-known theaters allll lit up and stepped foot in the Kimpton Hotel Monaco lobby which I stayed at the last time I was in Chicago with my Dad. The best part?! Finding a super fun set of gold ANGEL WINGS (!!!!) to strike *just a few* poses in front of. My college mascot is the Avenging Angel, so I ALWAYS will take an opportunity to pose in front of angel wings. That Monday night, I had a happy happy happy heart and SO MUCH love for the Windy City.

The other activity that we did was go to *none other than* the Target right next to the Malibu Barbie Popup Cafe after our time in Barbie Land to buy … Barbie dolls (!!!). The CUTEST thing?!?! SO many mothers, grandmothers, and daughters that we saw at the Malibu Barbie Cafe happened to stop by that exact Target, too. It was sooo fun to see Barbies manifested at Target afterwards! After Target, we took an Uber back to our hotel and ended up stopping by the iconic Intercontinental Hotel which was decked out in butterflies for summer time. We *of course* snapped a few photos with our Barbies at the hotel, too!

Where We Ate:

Starbucks Reserve Roastery – our first stop in Chicago was *none other than* … Starbucks Reserve! Starbucks Reserve is essentially a HUGE Starbucks offering cocktails, coffee, merchandise, food, and everything in between. It was such a neat experience! There isn’t a Starbucks Reserve in Washington, DC and I hadn’t been to the New York City Starbucks Reserve, so, when in Chicago, we HAD to make a visit (!!!). Lindsay and I went up to the 4th or 5th floor (I cannot remember – LOL!) bar and got some espresso martinis which were LITERALLY THE BEST EVER and simply enjoyed one another’s company. The vibes at the Starbucks Reserve were impeccable, too, and I will definitely be back for another espresso martini at the bar next time I am in the Windy City!

RL Ralph Lauren Restaurant – After seeing my friends Michelle and Divya dine at the RL Ralph Lauren Restaurant on their Chicago trip earlier in Summer 2023, I *just knew* that it was a must-dine when Lindsay and I went to Chicago! The restaurant is attached to Chicago’s Ralph Lauren boutique and the vibes were super elegant, classy, and very very very Ralph Lauren. The interior gave me a bit of that historic Washington, DC charm, but thinking more on the lines of Ralph Lauren in a restaurant! I tried their Lobster Bisque which was AMAZING and a Caesar salad. I have to mention that the staff at RL Ralph Lauren Restaurant are extremely kind, hospitable, and caring. While this wouldn’t be my first place on my list to dine at again in Chicago, I definitely wouldn’t hesitate to come back when the opportunity presents itself!

Hampton Social – Streeterville – Lindsay and I came to Hampton Social’s Streeterville Chicago location for a night cap on a rainy Monday night just a few blocks away from our hotel. We got Barbie-themed pink and glittery cocktails and I also got some delicious fried oysters. There aren’t any Hampton Social locations near me and I had heard of it as a popular spot in Nashville, SO I was psyched to hear that there were not one but TWO locations in Chi Chi! I am SO glad we came here, especially on a rainy Monday night as not many people were around and we got practically the entire second floor of the restaurant to admire its vibes and *of course* take photos.

Malibu Barbie Cafe – While the Popup cafe is unfortunately closed, Lindsay and I had an amazing time here. Upon purchase of our tickets, we selected complimentary food items (we both chose the veggie and grain bowl!) and ordered cocktails for an additional charge at the bar. The cocktails were ALSO glittery, pink, and VERYYY Barbie (!!!!). I’ll save the rest of my incredible experience at the Malibu Barbie Cafe for another post, but for now I will say that the food and drinks were pretty good.

Dollop Coffee Company – Lindsay and I got our morning coffees at Dollop Coffee just a block away from our hotel on Tuesday morning. One of the super fun things about Dollop is the fact that they have photos of many of the Real Housewives lining the walls of the shop. I don’t keep too much tabs at the moment on the Real Housewives, but I did watch the franchise a lot more during my high school years, so it was fun to see some familiar faces and enjoy a new-to-me cafe!

Wrap-Up:

I had an incredible time in Chicago and am SO grateful for our brief time in the Windy City. I LOVED the hotel that we stayed at and its location in proximity to many of Chicago’s incredible sites to see. I also LOVED having such a fun Barbie-themed time here, too. It was fun to practically plan a 24 hours revolving around all-things pink and Barbie! At the same time, I am so so so grateful for Lindsay’s and I’s friendship and the fact that she drove us into the city and then drove me to the airport out of the city, too. All in all, I have so much gratitude for our 24 hours in Chi Chi!

I definitely would LOVE to make a visit back to Chicago someday, too. And, hopefully, it won’t rain as much either! I would LOVE to experience the city’s incredible architecture via a tour, dine at some new-to-me spots, and spend time with Lindsay and others that I love. People in Chicago are extremely friendly and I would LOVE to go back again. Til next time the Windy City!

XOXO – Katie <3