Holiday Bucket List: Chicago Edition

Happy Monday, ya’ll! Hope you guys had a great weekend. I hosted a little get together on Saturday and then relaxed the remainder of the time (minus a final that was due yesterday lol)! With today being December 11 and the holidays in full swing around here (you can check out all of my gift guides here), I thought it’d be cool to share some of the things on my holiday bucket list this year. Last year was my first time seeing Chicago in all of its holiday glory, but I didn’t take advantage of it at all. However, this year I’m determined to do all of the fun things, and can’t wait to share!


I’ve been wanting to go to this market for an entire year, ever since I found out it existed last year! It’s the perfect opportunity to purchase gifts, as there’s tons of unique food, clothing and other little trinkets and items that you won’t be able to find anywhere else. It’s also super pretty, as it’s full of Christmas decorations and lights and the cutest little huts that remind me of ginger bread houses! The only thing is that you might want to get there early, as I hear the crowd gets super packed!

Millennium Park Ice Skating Rink

Okay, now this has been on my bucket list even before I moved to Chicago! I visited the city about this time two years ago and was dying to test out the ice rink, but the line was out of this world. I figure my best bet is to go at an off time, but it just seems like the most fun thing! I used to ice skate when I was really little, so being back on the ice definitely brings back those great childhood memories. It’s also super cool because there’s a restaurant on site, and just steps away from the iconic bean… the perfect place for photos!


I’m actually going to be able to cross this off of my bucket list on Saturday, as my friend and I are going to volunteer at a women’s shelter this Saturday! The holidays are my absolute favorite time of the year because it’s just so amazing to spend time with my friends and family, and everything just seems so much better. However, I realize there’s so many who aren’t as fortunate, and think it would be nice to help out even in just a small. Looking forward to this weekend, and hope it’s a much better time than last year because my mom and I tried to volunteer at a church and they got pissed at us because they said they had too many people LOLLL! It was so funny when it happened!

Shop the post below:

Sweater: c/o The Mint Julep Boutique (SO cozy! similar) // Jeans: GAP // Purse: Urban Outfitters (old, similar & less than $30!) // Boots: Nordstrom 

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  1. 12.14.17
    Jessica said:

    Your boots are sooo pretty, love the sweater too dear.

    Jessica |

    • 12.15.17
      Lauren O. said:

      Thanks a lot, Jessica! The sweater is seriously way too cozy!!

  2. 12.12.17
    Amy Arnold said:

    Fun list! the market sounds amazing. Loving this look too.

    Amy Ann
    Straight A Style

    • 12.12.17
      Lauren O. said:

      Thanks so much, Amy! The market is number one on my list, so hopefully I’ll get there soon!

  3. 12.12.17

    You look amazing! Love your booties!!
    Mónica Sors

    • 12.12.17
      Lauren O. said:

      Thanks so much, Monica! Glad you like them 🙂

  4. 12.11.17
    molly said:

    Such a good bucket list! I grew up in Chicago 🙂 so pretty at Christmastime.


    • 12.11.17
      Lauren O. said:

      Thanks a lot, Molly! I had no idea you were from Chicago! Everything is so gorgeous this year time of year!

  5. 12.11.17

    Those all sound like the perfect Christmas activities, Lauren! There are so many fun things this time of year, and it sounds like Chicago has a ton of options! Love your sweater, by the way!

    Baubles to Bubbles

    • 12.11.17
      Lauren O. said:

      Thanks a lot, Olivia! Christmas is seriously my favorite time of the year because there’s just so much fun stuff to do! Hope you’re doing well 🙂

Hi, I'm Lauren!

Thanks for stopping by! I'm a 20-something living in Cleveland, Ohio - sharing my love for all the things! If you love fashion, travel, reading, and local finds - then you're in the right place!