Destination: Chicago, Illinois

Hello, my lovely readers! So, it has been a travel-heavy year between Rome, Miami, and Paris, but I have yet another travel and fashion guide for a new city that you all seriously NEED to check out: Chicago!

For context, my boyfriend and I have been talking about going to Chicago since we first started dating almost four years ago, so this has been a long-awaited trip! So, when our annual Summer weekend getaway rolled around, we figured “why not finally do Chicago?”

– Shoutout to the best bf for making it happen and for making it such an amazing time!! Oh, and for being my personal photographer as usual, my Instagram feed and I are grateful –

Anyway, we arrived on Friday night and headed straight over to Lou Malnotti’s for some iconic deep-dish pizza. We ordered a small “Classic Chicago” pie (which is plenty for two people) and it was absolutely delicious! Was it as good as New York pizza? Personally, I don’t think so, but I’m a New York girl at heart so maybe I’m biased. From there, we walked over to Wrigleyville, which is a strip of bars and restaurants right around Wrigley Field. We spontaneously stopped into this bar called “BEER on Clark,” which had a twin bar connected to it next door. This bar boasted beer pong tables, arcade games, hilarious bartenders, and amazing throwback music from Jordan Sparks to Natasha Beddingfield. To say that it was a fun, carefree night and a perfect way to start off a great weekend trip would be an understatement.

For Friday night I decided to throw on a jumpsuit with flared, gaucho pant legs and an off-the-shoulder v-neck ruffled top in a fiery shade of red. I paired it with a basic jean jacket and my go-to tan pump heels to make it more of a casual look. While I typically don’t go for gaucho-style pants, I found this romper to be super flattering and fun for a night out on Chitown.

We woke up bright and early that next Saturday morning and took the very convenient L-train to downtown Chicago. Along the way, we passed by the iconic Chicago Theater and snagged a couple of pictures in front of it. I noticed that around that area there are some buildings that are vintage and gorgeous, while others are modern and refined. That’s one of the many aspects to Chicago’s unique nature; one minute it looks like you’re on the set of a 1920’s mobster movie and the next minute you’re standing in a spacious and clean New York City street. After the Chicago Theater, we walked over to Millennium Park and picked up some Chicago hot dogs on the way (which, for the record, are WAY better than New York hot dogs). After that, we saw the Bean and hung out by the Great Lawn before heading over to Michigan Avenue and splurging just a little at the Ralph Lauren store that looks like a mansion that doubles as a department store. After an 8-mile walk for the day (yes, we seriously walked 8 miles…) we decided to go to Raised, an incredibly beautiful, spacious and trendy bar right on the outskirts of the Chicago River. We took some pictures, drank some cocktails and indulged in a couple of appetizers before making our final stop at the Sky Deck of Willis Tower.

While I do recommend that you go see the Sky Deck if you find yourself in Chicago, there’s a couple of things to keep in mind. Firstly, the wait time to get up to the Sky Deck on average is anywhere from two to four hours, which is completely insane, for the record. If you’re like us and you don’t have all of that time to wait, they do offer a Fast Pass that’s 50 dollars a person and cuts the wait time down to anywhere from 15 minutes to half an hour. How much better is that?! In my opinion, it was totally worth it. Oh, and one more thing: if you’re expecting an entire floor made of glass then you will be disappointed. The Sky Deck is a normal floor with little boxes that are made of glass that you have to wait on ANOTHER line for. So, unless you are super passionate about pictures, have a blog, or have a saintly Instagram boyfriend, I suggest that you skip it. Although, the view was beautiful…for the two seconds we got to look at it.

For my big day of Chicago excursions, I opted to wear a black tank top dress with comfy t-shirt material and white stripes along the top of the dress that gives it a sporty feel. For shoes, I maintained the sporty and comfortable theme with my favorite pair of Adidas sneakers. I’m all about being trendy and fashion-forward, especially while exploring a new city, but why not be cozy at the same time?

Here’s the bottom line: I’ve been to a few different cities in the U.S., from Philadelphia to Washington D.C. So far, Chicago is my absolute favorite. So, grab a carry-on, grab a loved one, and head to Chicago; I promise you will not be disappointed!

Until next time,


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