48 hours in Chicago

Life has been pretty hectic lately with the last months of my college career coming to a close! So, Tim and I decided to take a much needed spontaneous trip to Chicago since it’s only four hours away from Cincinnati!

In today’s post I’m sharing all of the details of our trip! We basically ate and shopped our way through and I have no complaints about it. I hope you enjoy reading!

Where We Stayed 

We rented a cute, little Airbnb in the South Loop of Chicago. It was the perfect location! We were surrounded by a Stan’s Donut shop, Target, Starbucks, Trader Joe’s, and a bunch of restaurants! So basically I was in heaven.


What We Did

After getting settled into our Airbnb we decided to walk down State Street where all the affordable stores are and where the Chicago Theatre district is. We obviously had to stop at Urban Outfitters and Zara!



Later on in the night we decided to meet up with a few friends and get drinks. We went to a Jazz/Blues bar with live music called B.L.U.E.S. The band we saw has been playing there since 1982 which was awesome to see! We also went to Kirkwood, where I highly recommend getting their fishbowls!

On Saturday, we obviously had to explore the famous Magnificent Mile. It is 13 blocks of Designer shopping and cool restaurants! It was fun to just walk into stores like Gucci and pretend you could afford all of the things. Tim obviously did his fair share of bribing me into fancy car stores like Tesla.

After that we walked all the way to Navy Pier. Tim has never explored Chicago other than seeing the Bean so we had to do some touristy things!


Sunday morning we took a quick walk to see the Buckingham fountain. We weren’t thinking, by the time we got there we realized that the fountain wouldn’t be running because it was only 40 degrees all weekend. But it was nice to get our steps in and see the city!




What We Ate

Before checking into our Airbnb, the first thing we did was eat Giordano’s, of course! Tim and I have been craving deep dish pizza so naturally we went to Chicago’s famous. We created our own stuffed with chicken, bacon, pineapples, and peppers.


After walking around State Street, we tried walking into a few restaurants and all of them had 1-3 hour wait times to be seated! On our way back to our Airbnb we came across this place called Spanglish Mexican Kitchen. It was quick, casual, and the staff are so friendly! I got the chicken quesadillas (basic af) and Tim got a mix of all meat tacos.

On Saturday, I had to get Stan’s Donuts! Funny story, before getting to Chicago all I could talk about was how I needed to try Stan’s. When we pulled up to our Airbnb we found out it is RIGHT NEXT DOOR! It was fate! I got the old fashioned and a chocolate glazed donut. The chocolate glaze is so so delicious and just melts in your mouth.


After getting donuts, we took an uber to Somerset where we had some BOMB brunch. The place itself is a vibe of it’s own. It feels like a 60’s Yacht Club where all the servers are wearing light blue shirts or blazers and khakis! Everyone is very friendly there. Tim and I both got The Gold Coast Breakfast which has eggs, toast, potatoes and your choice of meat. Let me tell you what. The potatoes are to die for and I need to know what they put in them because they were addicting!



The last place we went to was DMK Burger Bar. The atmosphere is lively and fun! I do have to warn you it’s a bit dark but I guess it makes sense when you’re scarfing down burgers in public. I got burger number 1, which had cheddar, smoked bacon, charred balsamic red onion, and BBQ sauce. It was truly, one of the best burgers I have had. We also tried onion STRINGS not rings. They were life changing and addicting! I paired my meal with a local cider called Right Bee Cider. It’s a semi-dry sweetened with honey. Not only did the honey pull me in but the description of the beer said “Made by a man to woo a lady, this is truly a labor of love.” SOLD. It was worth it too!

So that ends my 48 hours in Chi-town. Let me know of more recommendations for the next time I go!



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