If you guys follow me on my Instagram (@fashiononafraction) then you would know that I went to Chicago last week. I went with my boyfriend and his friend and we were there for 4 days. None of us had ever been there so it was a new experience for all of us! We did so many fun and exciting things while we were there I thought I would share what we did and what I wore each day since all of my outfits were thrifted!
We mostly traveled this day and let me tell you, the drive from Minnesota to Chicago is long and boring. We decided to take the Amtrak train into Chicago so we drove to a suburb of Chicago and parked the car there and rode into the city. We made it with plenty of time to spare so we could have time to park and wait for the train. Since we were going to be leaving our car there,e for a few days we needed to park in the long-term parking area so our car didn’t get towed. They did not have any signs anywhere telling you where to go if you were going to be parking in the long-term area so we drove around for about 35 minutes and almost MISSED our train. It was so stressful. When we finally found the parking area (no thanks to any signs) we had a couple minutes until the train was leaving and we had to sprint about 3 blocks. Mind you I didn’t buy the tickets ahead of time because I wanted to make sure that we wouldn’t miss the train so we still didn’t have any tickets for the train. We made it onto the train and had to buy our tickets online while we were already on the train. After a long and stressful trip, we all needed a drink so we spent a couple hours at the hotel (complimentary) bar. We always stay at Embassy Suites because they have 2 hours of free drinks EVERY night (can you believe that??). After that, we needed some food so we decided to go to Giordano’s for some deep dish pizza. It was soooooo good but if you are going to get deep dish to be mindful that it takes about 45 minutes to cook so order before you’re even hungry!
I got this dress out of a liquidation box that I had gotten recently, but the brand is Socialite. This brand is sold at Nordstrom and they don’t the exact dress, but they have this one in a different print. I think the polka dots are super cute and would look so cute with a leather jacket and boots to transition into the fall season!
Right away in the morning, we decided to go thrifting so we walked to the closest thrift store from our hotel. It felt like 100 degrees outside so by the time we got to thrift store we felt like we were dying of heat exhaustion. Then we realized that thrift store didn’t have A/C so we had to hurry up and look through a few racks and then check out. We order a lift for the ride back to the hotel because we could not walk all the way back to the hotel (it was 1.5 miles).
You can’t see my dress in this picture, but it a really cute Gap denim dress with an open back detail. I got this at a thrift store in San Francisco when I was there in the spring. It is super cute on and it has pockets!! Exact, Similar I found a few options on Poshmark, but I could only find one listing of my exact same dress!
After that, we decided to some shopping along the Magnificient Mile. The shops down there are absolutely stunning. I wish I could afford everything in every store, but sadly I am not on that level of “treat yo’ self”. We walked along the entire street and then when we got to the end we decided to go up to the John Hancock building. We didn’t go up to the observatory deck because it costs a ridiculous amount of money to go up there so we decided to go up to the bar. We got a drink and it was less than half the price for a ticket up to the observatory and to do the tilt part. Plus the bar/restaurant is 2 floors higher so you have a better view! It was absolutely beautiful!
Then at night, we decided to venture a little outside of the city and go to the Green Mill, which is the Jazz place that Al Capone used to frequent back in his days. We actually sat in the exact booth that he used to sit in which was cool and creepy at the same time. We stayed for 2 sets and the Jazz was the best I’ve ever heard. Everyone in the band was AMAZING. I would definitely recommend going! It was really packed though and you are not allowed to talk during the performance so beware of that. They will come up to you and ask you to stop talking if you are talking.
We got a little bit of a late start in the morning because we were so tired from the night before, but we went to the Chicago Cultural Center and the Art Institute of Chicago. I really like seeing the dome at the Cultural Center. It was crazy how big it is in person. I couldn’t even get all of it in one picture. We walked from the Chicago Cultural Center to the Art Institute and we walked past the Bean on our way so naturally, we had to stop and take a picture (and get a snack). Then we walked through the Art Institute and saw most of the art that they had to offer. That place is huge so if you plan to go make sure you schedule the entire day for it or know what areas you want to see. We tried to get through everything, but we just couldn’t do it.
This is the same dress that I wore on my 22nd birthday! It is a Missoni X Target and I absolutely love it! I made a post all about it that you can read here.
Then we decided to walk to the Navy Pier. This was a terrible idea because the walk was so far from the Art Institute. All of our feet hurt really bad, but we had already committed to doing it that we couldn’t turn around. When we finally arrived after what seemed like an eternity we got something to drink and went to the Ferris Wheel. You can’t take food or beverages onto the Ferris Wheel (sadly I had to throw my drink away) so I would go on the Ferris Wheel before you get something to drink/eat. The Ferris Wheel was so much fun (a little pricey, but worth it) I would also recommend making sure you do this while you’re there!
There is also a children’s museum on the Navy Pier so if you have kids that would be a good thing to take them to! They have a greenhouse/ conservatory area that was really fun to walk through and see. It isn’t very big, but they have a couple different water features that are cool to see.
This was our last full day in Chicago so we were trying to do as many things left on our list as possible. We had something scheduled to do later in the day, but we were left with a weird open gap in the morning so we decided to go check out the Lincoln Park Zoo. This was honestly one of the best zoos I’ve ever been to in my entire life and it was FREE. I couldn’t actually believe that it was free, but this would be a great place to take your kids for a day and hang out. Even if you’re an adult this would be fun. It is also a really big zoo that we didn’t even get through everything and we were there for 1.5 hours!
It was cold and rainy this day so I wore a Marc Jacobs shirt that I had listed in my Poshmark closet for the longest time, but it wasn’t getting ANY interest so I decided I would put in my closet. My jeans are Calvin Klein and I wear these all the time. They are perfect for work (if you work at a business casual place) because they are stretchy and don’t make you feel restricted when you’re sitting down. There is nothing listed on Poshmark that is similar to my Marc Jacobs top, but I found a few jeans that are similar to my Calvin Kleins. Similar, similar, similar.
Next, we had scheduled an Architectural Boat Tour through Groupon. I found tickets there for 50% off of the original cost which saved us a ton of money! The tour guide on our boat works for the History channel and I am pretty sure I have seen him on a few different shows on there. This was my absolute favorite part of our entire trip! The tour lasted a total of 1.5 hours and it went by so fast! They have drinks and snacks on the boat for purchase. They give you so much information about all the buildings along the river. They talk about the architecture (obviously), the history behind the buildings, and what they are now used for. They tell you so many interesting facts that it was hard to remember everything he told us.
After the tour, we were starving so we decided to go grab a bite to eat at the RL restaurant. The restaurant is attached to the Ralph Lauren store (which is the largest location in all of the US). We did a little bit of shopping in the store before we headed over to the restaurant side. We both got burgers and they were really good. I would recommend going here for a bite to eat if you have time to sit down for a nice meal while you are in Chicago. We went during the day for a little bit of a late lunch, but if you went for dinner it would definitely be a place to dress up for. We walked back from the restaurant to our hotel and we got caught in a rainstorm. We were both soaking wet by the time we made it back to the hotel. It was terrible at the time, but looking back at it now it was really funny.
For our last night, we really wanted to go see a burlesque show, but none of the places were open on Wednesday night (I mean its a Wednesday doesn’t everyone want to see a burlesque show?). We ended up going to an underground bar which I was really nervous about, but it was really cool when we got there! They change up their drink menu every week, but their menu is on tarot cards. It was really small on the inside, but it had a really interesting atmosphere. They do small shows and performances every hour. We only stayed for one show, but it wasn’t anything great. You have to pay a cover of $4 to get into the place so the performances weren’t going to be anything outstanding I thought.
Places I Would Recommend:
The Navy Pier
Architectural Boat Tour
Green Mill (not the best neighborhood)
Things I Wish I Would’ve Done:
Go to the Willis Tower and stand on the glass
Ride a bus tour through the city
See a burlesque show
See a play/ theater performance at a theater
I hope you guys enjoyed reading this post and got some ideas for a future trip! Let me know what you have done in Chicago if you have ever been and what you would recommend!