Outfits For a Quick Trip To Chicago + My Favorite Spots

Last week I popped into Chicago for two days to attend 29Rooms for a job! I hadn’t been to Chicago since this trip years back, so I was pretty determined to make the most of my two days there! I really wanted to revisit some of my favorite spots, but also try some new places I hadn’t been yet. I think we did a great job of accomplishing that goal! It’s funny that as a NYer I basically never go to touristy spots like the Statue of Liberty or the Empire State Building, but in another city it feels exciting to be a tourist. So yes, some of my spots I realize are stereotypical and touristy, but what can I say, I’m cheesy like that!

SEARS TOWER / THE SKYDECK

I’ve been here before when it was insanely busy, but on this day it was rainy and they were telling everyone there was 0 visibility, so the entire place was empty. It was amazing! I’d suggest going right at open if you don’t want to wait in insane lines, but the experience as a tourist is so cool and completely worth it!

 

JOJOS MILK BAR

A follower recommended this spot, and we saw the sundaes and had to stop in. It was SO good and also I don’t think I’ve ever seen a prettier sundae in my life! The only thing I was sort of disappointed in, and it’s such a blogger problem, but the lighting inside was a bit dark. For some reason I just expected it to be bright and airy, and it wasn’t at all.

HAMPTON SOCIAL

If you’re looking for a delicious and instagrammable brunch spot, this is your place! The food was SO good (I got a beach bowl with avocado and beans it was delicious) and the entire space was so beautiful too! I’d suggest making a reservation because even on a weekday mid-day it was busy!

 

 

THE BEAN

What’s a trip to Chicago without a stop at the Bean? It’s always more impressive to me in person, and it’s such an interactive piece of art which is hard to grasp from photos. A lot of you have asked how I got a photo of it empty, and the truth is we woke up at 7AM to get the shot, but it was raining. We waited for a while under an awning in the rain, and it was actually really peaceful and aesthetic watching the rain drip off of the bean. It was forced time to slow down! Once the rain stopped we were able to get empty Bean photos, which was an added bonus!

 

LOU MALNATIS

We stopped in here late night for some deep dish! It was sooo busy and took a while to get our pizza, but was worth every bit of the wait – although I still prefer a NY slice any day!

 

That’s about it for what we were able to accomplish in a two day span! I hope you en joyed the photos, and make sure to save the guide for your visit!

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