A Holiday Bucket List in Chicago + A Party Outfit!

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!

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!)

Holiday Bucket List in Chicago

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.)
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!
Santa Baby Bar ✔️ Do it for the ‘gram! You can see a preview in my IG Highlights.
Rudolph’s Bar ✔️ Similar to Santa Baby, but The Grinch Bar here was my favorite!
Christkindlmarket Wrigleyville I’ve yet to go to the newest Christkindlmarket location up at Wrigley!
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.
Igloos at The Godfrey I’ve never done an igloo, but they seem super cute!
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.
Frosty’s I haven’t been to Frosty’s yet either, but it also looks insane!
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!
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!