Note: this was first published in 2018, but I’ve updated it over the years. You can see my big 2022 holiday bucket list in a new post!

I was reminded recently that my very first visit to Chicago was right before Christmas (well over a decade ago!) and I thought about the energy I felt from the hustle and bustle along Michigan Ave. and the snow flakes swirling around, how different it was from where I grew up, and how lucky I am to call this place my home 12 years later.

I have dreams to spend time in London, Quebec, and NYC during the holiday season when travel restrictions ease and planning feels less strenuous.

I fall in love with the city all over again this time of the year and the holiday season always goes by in the blink of an eye, so I rounded up the most fun and festive things to do in Chicago during the holidays to help us all make the most of it. So much was closed last year due to Covid and upon updating this list, I was devastated to find so many of my favorites have shut their doors for good. Augie’s, Booth One, Hush Money, and so many others are no longer. It probably goes without saying now, but it’s always best to check with an establishment beforehand (to save you from disappointment) as things continue to be ever-changing with the pandemic.

Think of this as your Chicago Holiday Bucket List! But it shouldn’t go unmentioned you can do a lot of these things well into the new year, too, as it never hurts to have a few activities tucked in your back pocket for the month of January which seems to last forever and a day.

Hope this list helps to make your spirits bright!

Visit Mindy’s Bakery in Wicker Park for a decadent cup of hot chocolate–Chef Segal’s specialty–with a house-made marshmallow (Exhibit A). And if you’re not in the neighborhood, you can find an assortment of Mindy’s baked goods at Foxtrot’s across the city to go along with one of their peppermint lattes. I mean…..YUM.

Unwind from the week and see the Christmas decor at Butch McGuire’s pub or make an afternoon of it one weekend with friends where you can sip libations while the holiday train circles around the top of bar! 

Gather your group and post up at Camp Lottie’s for a Christmas movie night and take your pick between their Nice or Naughty Flix showtimes.

Spend the afternoon in the game room at the Chicago Athletic Association. I highly recommend a glass of bubbly and their lime popcorn. You can’t go wrong with their giant pretzel, either. After that, head to Happy’s inside the hotel. Their holiday popup is all about the warm vibes, seasonal tunes, and boozy hot cocktails!

Enjoy a Jazz Brunch at The Dearborn.

Put on your Sunday best and get your girlfriends together for Holiday Tea at The Drake!

Go on a walking Holiday Cheer Tour to see all the Christmas decorations around the city. Some of my favorite trees can be found here! And don’t miss the Peninsula, which is looking extra pretty this year!

Order pizza pies for the table and enjoy a slice (or three) under the twinkle lights and holiday decorations at Happy Camper, Homeslice, or Paradise Park!

Cozy up at a restaurant/bar with a fire place. Some of my favorites are The Drawing Room at Chicago Athletic Association, Hubbard Inn, and The Dawson. Scofflaw, The Broken Shaker, Range, Table, Donkey, and Stick, Sheffield’s, Wild Bar and Restaurant, Ralph Lauren Polo Bar, The Moonlighter, Tied House, and The Violet Hour are on my list for the winter months ahead, too!

Visit the Jack Frost Winter Village & Christmas Tree Farm at Goose Island for all the outdoor fun, ice skating, holiday drinks, & more!

Have a drink at Santa Baby Bar or Rudolph’s, which are both over-the-top, decked out Christmas themed bars in Wrigleyville! You can get a peek at their 2021 decor in this reel I put together!

Don’t miss The Matchbox (Chicago’s smallest bar!) and Foxbar are all done up for the season, too!

Catch it if you can! Take a ride on the CTA Holiday Train. It’s all decked out and would make any commute infinitely better, in my opinion.

Guthrie’s Tavern is a really laid-back spot for a night of old school board games and microbrews.

Indulge in a brownie in the Walnut Room at Macy’s. This Chicago Tradition is said to have an incredible tree, too!

Join the kids at Off the Street Club for a holiday edition of Third Thursday! They put on a performance and it is truly the best time. You can RSVP here.

Shop the vendors at Christkindlmarket with a grilled cheese pretzel in one hand and German-style beer in the other. And if beer isn’t your thing, warm up with a glass of Glüehwein in a festive boot mug that you can take home with you!

If you’re looking to let loose it’s always the best time renting a holiday party trolley with friends for a night out! Pack a cooler, put together a great playlist, and get your Instax camera ready to capture the night, and don’t forget the film!

Visit Alice & Wonder in Lincoln Park or Southport to see the decorated storefront and pick up a few gifts for friends and family! Or, you know, a little something for yourself. Their holiday shop is one of my favorites every year and I love supporting a local, woman-owned business.

Embrace winter rooftop season at The Godfrey in one of their igloos! Or make a day of it in one of the igloo domes at City Winery on the Riverwalk. I also think this would make for a fun outing with coworkers.

Bundle up, grab a bag of Garrett Popcorn, and walk through Cloud Gate. They also offer caroling on certain days of the week if you’re into that sorta thing.

Spend an afternoon at The Museum of Science + Industry for the Christmas Around the World and Holidays of Light experience.

Visit Lightscape Chicago, which is an enchanting, illuminated trail at the Chicago Botanic Garden (just north of the city) for a dose of pure magic. A quick note: be sure to scroll down on the page for all the details.

Lace up and go ice skating at Millennium Park or Maggie Daley Park.

There are so many festive things to do in Chicago during the winter months and I’m sure I missed something, so let me know your favorites down in the comments! And be sure to tag me on Instagram and let me know where you end up 🙂