Chicago Travel Diary

Two weekends ago I took a long weekend getaway to Chicago to visit one of my best nursing friends, Anna! She recently moved there in July, and I couldn’t wait to visit her since I’d never been to Chi town before! I worked Thursday night and had my flight at 9:45am on Friday morning…talking about looking like death at the airport! I clocked out of work at 8am and went straight to the airport to catch my flight… oy.

Friday: My friend lives in a great location.. super close to the lake, river, Michigan Ave, and the bars! I arrived around 11am on Friday, and I took a nap until 3ish (#nightshiftprobs). We headed to dinner at Café Luxe and then headed out the Wit rooftop bar and later to Hubbard Street. Chicago even has some “late night” bars that stay open until 4am… so obviously we went to those. Why? I have no clue, apparently we were trying to act like we were 22. Well… it hit us hard because the next day we didn’t wake up until 2pm!!!

Saturday: After slowing getting ready and almost dying (drank a little too much the night before), we headed to Beatrix to grab some much needed food. Burger and fries plz, needed all tha grease. We headed down to the river for an Architecture Tour

It was actually very interesting and fun to see the city in another view.


similar floral romper and here (less than $30) and here

A picture of us by the Chicago Riverwalk, where the Architecture Tour started!

After the tour, we headed to the Hancock Building

to take in the city on the 96th floor! It was a long wait, and I don’t think I would recommend it. The drinks were crazy expensive, and we paid $18 for a cheese dip that was paired sliced bread from the grocery store. I definitely wasn’t impressed, because vibe isn’t that welcoming or inclusive. You sit at individual tables and order drinks. You don’t really mingle around or talk to anyone else besides your waitress/waiter and whoever you came with. Everything was also crazy expensive, the drinks and food weren’t that good, and it’s about a 45min-1hr wait! After we ditched that place, we headed to Bub City, a country bar in Chicago…which I also wouldn’t really recommend. They have a live band and a $5 cover. The live band was good, but so loud that you couldn’t even talk to the person rubbing shoulders with you. We were over that place in 30 minutes, so we headed down the street to Untitled Supper Club

And man, Untitled is seriously so much fun. It’s so big, and has such a great layout with three bars! There is a designated dancing area, so you’re not constantly being bumped into if you don’t want to dance. I would highly recommend going to Untitled if you’re visiting Chicago. The DJ was also spot on, the bartenders were nice, and there was never a line for the restrooms (I mean… that deserves an A++ in my book when it comes to bars)

Sunday: We woke up early and headed to the Flamingo Wall that was listed on The Every Girl’s Top Ten Instagrammable Spots in Chicago

One word: obsessed.


similar fringe sweater // pleated shorts // lace up sandals

Then we headed to the #instafamous restaurant, The Hampton Social

We obviously had to take a picture with the ‘Rose All Day’ sign… I mean I’d be lying if I said we didn’t ask people to move so we could take a picture, oops! #priorities.



similar fringe sweater // pleated shorts // lace up sandals // gold arrowhead necklace

Then we headed to the Bean.. because well obviously.


SheInside floral maxi c/o // lace up sandals //  GiGi New York crossbody // Bobbi Brown lipstick in ‘crushed plum’

Next up was Cindy’s

which is another rooftop bar. Cindy’s has the most incredible view (see below) along with really fun and delicious drinks. I got Grey Garden (pictured below) and the We’ll Always Have Paris. Both were amazing, but if I had to choose one, it’d be We’ll Always Have Paris.



This was probably one of my favorite places we visited! The people were so nice, the drinks were delicious, and the views weren’t that bad either 😉

Then we headed down to the 1st floor which is another bar called Gameroom

We played a couple games for awhile, and I also really like that place. Lots of space, nice people, and a ton of games! Next, I wanted to try deep dish pizza. We headed to Lou Malnati’s

and it was so so good. I was a newbie for deep dish pizza….and I’m already wanting some more. We ended our day at JParker’s rooftop for a relaxing cocktail before heading home.

Monday: We woke up early again to head to Skydeck at Willis Tower

We arrived at 8:50am, because we didn’t want to wait in a long line (it doesn’t open until 9am). There were probably around 20 people already there, but we went straight upstairs once the doors opened. It was perfect because no one was really there, so we had a lot of time to take pictures on the SkyDecks. Anna was saying how she was scared the entire time we were walking our way through the line, and I thought it wasn’t going to be a big deal. Well boy, was I wrong. I thought ‘Oh I’ve been in tall buildings before, it’s basically the same thing.’ Oh no no no. It’s completely different stepping on glass where you can see straight down. It was scary! The tickets cost $22, so you’re basically paying $22 for a photo… but it was a cool experience, and I’d do it again!


Club Monaco top (on sale!) // similar distressed jeans (less than $70) and here // similar lace up sandals

^^ me seriously crawling back to safety, because it was scary!!!

Next we headed to the Lake to have a mini ‘beach day’ before my flight in the afternoon. It was so crazy seeing the skyscrapers to my left and just sincerity right in front of me. I’m from the Virginia Beach area, so I’m used to a relaxed atmosphere near the beach.. and this was a 180. Hustle to my left and relaxation to my right.

Overall, I fell in love with Chicago! I would move there in a heart beat if the weather was brutal 9/10 months out of the year. It was even a little chilly if we weren’t in the sun when I was visiting, so I’m a little scared to see what Chicago winters are all about. Now, I can’t wait until Anna comes visits me in DC! I miss her already 🙂


1 Comment

  1. Brian
    September 28, 2016 / 11:52 am

    Glad you got to visit your friend. The two of you look fantastic. Great pictures of Chicago, makes me want to visit. Except that glass bottomed floor, that makes my knees weak.

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