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I went to Chicago for the first time on the most random days of the week and during the coldest season! I went from a Sunday morning to a Wednesday night.  I thought finding lit things to do would be a bit of a struggle, but I was actually able to find some pretty cool places. So here’s a few of my recommendations.


1. THE SUGAR FACTORY – I’ve been to a few of their locations across the states so I figured it was only right to try it out in Chicago since it never seems to disappoints. Plus, it was my friend’s birthday, so why not celebrate there? Their drinks are a bit pricey but big enough to share. Even if you decide not to share, the drinks are big enough that you’ll only need one.  For my drink I got the Mai Tai which was pretty strong compared to the rest of the drinks that my friends ordered, but very delicious! I also got The Ultimate Veggie Burger which was amazing.Processed with VSCO with al6 preset2. AJIDA JAPANESE GRILL & RAMEN- I’ve always had a love for ramen, so we decided to go ahead and try a cool place I found online. This place was pretty cozy and relaxing. The menu wasn’t huge, but they had a great deal! We ordered an appetizer, a bowl of ramen, and a drink all for $14 and it was definitely worth it.1EBEE5E1-0A49-45B9-82F9-75A330B81F3CProcessed with VSCO with a3 preset3. RAISED URBAN ROOF TOP BAR – If you’re looking for a nice rooftop vibe, this is definitely the place. We went on a Monday, so of course it was fairly empty but the view was to die for. The drinks were great and the service was even better. Inside and outside you could get a great view of the city, very Instagram worthy.  I have a huge fear of heights so it was a plus that this beautiful view was only three floors up. I live for a good rooftop vibe, so I absolutely loved this place. This Urban rooftop bar is nice no matter the day of the week or the season because even in the winter they have the fire pits on outside to make sure you stay warm!Processed with VSCO with av8 preset4. HOT WOKS COOL SUSHI – We ended up at this place simply because it was close to Union square and it was freezing outside, but to my surprise the atmosphere was so nice with beautiful art on the walls and the food was great! I ordered the salmon teriyaki bento box. I’m usually super picky about where I order salmon from but this did not disappoint. Processed with VSCO with au1 preset5. SPRINKLES CUPCAKE ATM – This one is just for the experience! We walked 40 minutes just to go to this pretty ATM. Yes, I know we’re insane for doing that in Chicago weather, but I had to see it for myself. There was actually a store but the ATM is just a pink pretty box where you order your choice of cupcake and it just pops out for you.Processed with VSCO with fp8 presetProcessed with VSCO with fp2 preset 6. NAVY PIER – This is pretty close to the cupcake ATM, so might as well try both! Since we walked, we got to Navy Pier too late to see much of anything. But, there is a huge Ferris Wheel and a lot of nice little shops. I was able to see a few stores before they closed which had lots of cool clothes, soaps, etc. I also got to try a slice of pizza there, which wasn’t too bad (nothing like NYC Pizza though.)We found out everything closes around 9pm on the week days, so if you’re going to try Navy Pier during a weekday make sure to get there early!Processed with VSCO with c6 presetAll in all, Chicago was a pretty fun experience. If you come prepared for the weather in the winter time, you’ll love the brisk air. The city was clean and the skyline was breathtaking. Even if you’re staying slightly outside of the city, the train is easy to figure out and it’s only an $8 ride! I’ll definitely be back because I know there’s a lot more left to see!

6 Comments Add yours

  1. Tea says:

    Love this!!!!! Great job Asj ❤️

    Liked by 3 people

  2. Gabe Williams says:

    THIS IS GREAT!! Very helpful!!

    Liked by 2 people

  3. Jerae Quadasia says:

    Super Informative, bomb pictures sis!

    Liked by 2 people

  4. Ez says:

    Cool post. During my recent visit I stopped by the Virgin Hotel that is also pretty cool with amazing view from the roof top bar.

    Liked by 2 people

  5. Having your baggage will become much simpler.


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