Starting off my 28th year in Chicago!

My fun weekend in Chicago is over and I’m officially 28 … SADS.  So I’m going to tell you about it so I feel a little better. 🙂

I started off my day at the gym since I wouldn’t be working out or counting macros all weekend (oops). After my workout, I headed off to Milwaukee to take the 1 p.m. train down to Chicago! Of course, I took all of my photos on Snapchat, so I don’t have any of them. Whoops. But then, look! I was in Chicago!


Julie wasn’t in the room when I got there and I, of course, was so excited to finally meet her that I didn’t take any pictures of our GORGEOUS room. Seriously. The Godfrey Hotel in Chicago was amazing. I headed to the hotel bar and Julie and I ended up talking for HOURS until finally heading back to the room to get ready to go to dinner. I did take a quick photo when I was up on the bar later that night.


We ended up going to Roka Akor for sushi (recommendation by my friend, Brooke!) and it was amazing. The food was great and the service was even better.

Roka Akor

They gave us oysters on the house, so that was an interesting first experience for me. I would say my favorite roll was the one that kind of looks like there’s an egg on the top (the bottom right picture). Yum!

Julie wasn’t feeling well, so we ended up going to back to the hotel and going to bed. I wasn’t disappointed at all, though! She fell asleep right away and I messed around on my phone before going to sleep. Unfortunately we could hear almost everything happening in the hallway, (that’s the only back thing I have to say about the hotel) so I ended up having a hard time staying asleep.

We woke up pretty early on Saturday (my birthday!) and took a bit to chat and then get ready. It was GORGEOUS in Chicago – 47 degrees and sunny in January which is almost unheard of in the Midwest. We took that as a perfect opportunity to truly explore the city! First stop was Starbucks for caffeine and apparently it was also National Croissant Day and Julie couldn’t believe I had never had one, so I got a chocolate one. Yum.

Croissant Day

P.S. Yes, we did wear matching blanket scarves around Chicago. 🙂

We walked all over, and I snapped a few pictures. All very appropriate and mature, as you can see.

Trump Tower

I love the middle finger emoji.

The Bean

Of course we had to get a few pictures at The Bean as well as make new friends that had the same scarf as us. Apparently it’s a very popular style!

The Bean

We walked all over Michigan Ave and stopped in a few stores. I drooled over the stuff in Kate Spade and we both picked up a few things in Sephora. Julie bought some Garrett’s popcorn and a ton of candy.

Julie & Jessie

Chicago River

We then headed to Gino’s East so Julie could have her first deep dish pizza! Of course we were only able to eat one piece each before feeling like death, but it was good!

Gino's East

After Gino’s we walked back to our hotel and ended up laying around for awhile, while eating massive amounts of candy. Here’s a dramatization:

Girls Night

We spent probably over an hour just trying to figure out WHERE we should go for dinner (too many options) and I introduced Julie to Tinder so we were messing around on there for awhile, too. Fun fact: Chicago men are WAY hotter than Green Bay men. At least the ones on Tinder.

Finally we started getting ready and ended up just eating in the Italian restaurant in our hotel. It wasn’t anything insanely great, but the service was amazing.


After dinner we tried to head up to the bar in the hotel, but apparently there was a private party so we got shot BACK downstairs to fight our way into the party. We stayed awake until 2:30 before they kicked us all out and then we went to bed.


We woke up the next morning earlier than expected (stupid body) and spent our last couple of hours in the hotel. We were going to get froyo for breakfast because #vacation but decided that was too much work. So we got donuts at Glazed & Infused. 😉

Glazed & Infused

Glazed & Infused

Julie and I then had to part ways 🙁 She went off to the airport and I went to the train station. I was so tired and my card wouldn’t work in the soda machine, so I had no caffeine and felt like I was dying. I got to Milwaukee, went to Trader Joes and then went to Saige’s house for the night. Thank God – I was so tired, I can’t imagine driving two hours home. I had off of work on Monday, so I went home in the morning, took a nap, worked out and then got as many things done at home as possible.

Oh, and apparently 28 means you get purses for your birthday and I am TOTALLY okay with that. Julie got me a Kate Spade clutch which was unexpected and super exciting …

Kate Spade

… and I came home to a crossbody bag from my cousin Debby!

Nicole Miller

Now I just have to go buy myself a smaller wallet for the bag and then I can switch over from my giant bag!

That was my weekend! It went by quickly, but it was a lot of fun. Now I’m back at work trying to get back into the swing of things and sort out a few things that magically didn’t get finished while I was gone (ANNOYING). I work both jobs today and there’s supposedly a huge snowstorm coming in, so I’m kind of hoping the gym closes early tonight though I’m not banking on it.

How was your weekend?



  1. Megan says:

    Your birthday weekend sounds amazing! And how sweet of her to get you something for your birth day too! All your pictures really make me want to visit Chicago! I haven’t been there in about 20 years so I don’t really remember it, haha. I’m glad you guys made it out on Saturday night too! 🙂 That picture of you with the wine & ice cream is great.
    Megan recently posted…weekend recapMy Profile

  2. Marette @ Floradise says:

    So glad you loved Chicago! I did rooftop yoga and mimosas at the Godfrey Hotel and it was so much fun! I need to add that doughnut shop to my list; I haven’t been there yet. Happy belated birthday!

  3. Liz says:

    Love this! HAPPY BIRTHDAY! I felt like 28 was a good year 🙂 And I love Chicago so how fun that you got to go! I’ve only gone for a weekend for an Army thing, but we had a fair amount of free time to walk around so I at least got to see some stuff. But I’ve been dying to go back! That’s so sweet of people to get you gifts! I never buy people gifts unless I attend some sort of shower for them, but we’ve gotten a bunch of gifts for the baby lately and it makes me realize how nice it is to get gifts! That donut looks so good! I WANT A DONUT!!!
    Liz recently posted…Anniversaries, Nesting, and Other Life HappeningsMy Profile

    • Jessie says:

      Thank you! I’m really hoping it’s my best year yet. 😉 I’m with you on gifts – mostly because I’m poor. Definitely wasn’t expecting anything!

  4. Cait says:

    how fun friend! i just moved from chicago to atlanta last year and your post is making me miss my city! so glad i came across your blog!

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