My Holiday Bucket List

Chicago fashion blogger Jessica Sturdy of Bows & Sequins wearing a teddy coat and shimmery dress.

I couldn’t be more of a “list person” … If I don’t write something down, it will never get done, and if I don’t put something on my calendar, it will never happen. I’m obnoxiously OCD about it… Lists are one of the few things that wrangle my anxiety and bring my swirling thoughts back down to planet Earth. So as you can imagine, even when it comes to fun things, I like to have a concrete list to make sure I’m making progress!

Chicago personal stylist Jessica Sturdy wearing a shimmery dress in front of The Ambassador Hotel in Chicago's Gold Coast.

The holiday season feels pretty short this year, especially since I’ll be out of town next week, but I’m determined to soak up all of the holiday magic that I can! Here’s what’s on my list, plus some ideas if you’re visiting Chicago over the holidays. (Or playing tourist in your own city, like me!)

Fashion blogger wearing a sparkly dress with a teddy coat.

Holiday Bucket List in Chicago

  1. Christkindlmarket ✔️  I went a couple of weeks ago and it did not disappoint! If you’re going with a large group, reserve an indoor table of 8 (we had two tables!) for $29/person. That includes a keepsake mug for everyone and a pitcher of mulled wine! BUT DON’T MISS THE RACLETTE! Omfg, I’m going to need that salami sandwich again before the season is over. The stand you want to go to is right at the corner of Dearborn & Washington, right outside of the market entrance. (Watch my ‘Holiday’ Instagram Highlight for a visual.)
  2. Zoo Lights   I haven’t been to Zoo Lights in a number of years, but it’s always a great way to get into the holiday spirit!
  3. Santa Baby Bar ✔️  Do it for the ‘gram! You can see a preview in my IG Highlights.
  4. Rudolph’s Bar ✔️  Similar to Santa Baby, but The Grinch Bar here was my favorite!
  5. Christkindlmarket Wrigleyville   I’ve yet to go to the newest Christkindlmarket location up at Wrigley!
  6. Ice Skating   There are so many different rinks to check out (at the Bean, the Maggie Daley ribbon, at the Peninsula Hotel, at Gallagher Way, at the Lincoln Park Zoo) and while this is such a fun holiday activity, I’m thinking I may save this one for after the holidays when crowds die down.
  7. Igloos at The Godfrey   I’ve never done an igloo, but they seem super cute!
  8. Festive Bars   My friends and I rent a trolley every December (and dress up in our tackiest holiday garb!) and visit all of the more divey bars decked out in lights and ornaments… Butch McGuires, Lottie’s, Burwood Tap, etc.
  9. Frosty’s   I haven’t been to Frosty’s yet either, but it also looks insane!
  10. See the Trees!   There’s always a great one at the Wrigley Building, my favorite indoor tree is at the 900 Shops, and while the one in Millennium park has nothing on Rockefeller Center, it’s worth seeing if you’re in the area!
  11. Second City   Seeing a show at Second City is always a must-do in Chicago, but their holiday show looks like it would be a blast!

If you’re looking for even more ideas, Conde Nast Traveler just posted a very extensive list!

Fashion and beauty blogger wearing a shimmery copper and silver dress with a teddy coat for the holidays.

Chicago blogger styling a shimmery mock neck mini dress.

Shop My Outfit…

Chelsea28 Shimmery Dress (similar here & here)
Sanctuary Teddy Coat (currently 40% off!)
J.Crew Copper Pumps (old; similar here, here, here, & here)
Brahmin Faith Bag
Capwell + Co Bangles (also available in silver!)
Pavé Rose Gold Band Ring
Loren Hope Earrings

Fashion blogger carrying the Brahmin Faith bag.

Chicago fashion blogger Bows & Sequins styling a shimmery mock neck dress.

Outfit blogger wearing a brown teddy coat with a party dress.

Chicago fashion influencer Bows & Sequins wearing a burnt orange teddy coat with a sparkly dress and copper pumps.

Lifestyle blogger wearing a shimmery dress with a teddy coat for the holidays.

Chicago blogger wearing a teddy coat and party dress.

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Leave a Comment


  1. 12.12.19
    Cynthia said:

    Second City is the best!

    • 12.12.19
      Jessica said:

      Couldn’t agree more!