Flags Candy Wine

Flags Candy Wine

Share this post

Flags Candy Wine
Flags Candy Wine
Chicago Holiday Time
Small Snack

Chicago Holiday Time

Things to eat, drink and do to make the most of Holiday Time in Chicago.

Ryan Maconochie's avatar
Ryan Maconochie
Oct 03, 2023
∙ Paid

Share this post

Flags Candy Wine
Flags Candy Wine
Chicago Holiday Time
Share

I’ve bounced around Chicago long enough to know that there are far better things to do in this city during the holidays than just hang out at the holiday pop up bars.

There’s lights to admire, parties to prepare, cheer to spread.

There’s Tom & Jerry’s to savor, raclette to relish, Santa Trains to track down.

There’s sledding, sightseeing, shopping, tippling, tea timing, and treelighting to enjoy.

Friends to be met. Gifts to be given. Dining to be done.

These days, most places spruce up their bar or restaurant with some holiday decor, but some are better than others at achieving a certain, festive, atmosphere, and the charm is not always relative to the amount of lights that get strung.

Below I’ve collected my favorite places to go and things to do during the holiday season in Chicago. Most of these can flex to be enjoyed by a small group of adult friends, or they work just as well with a family. Even Butch Mcguire’s has a kids menu if you can believe it.

It’s fun to string a few of these things together in an afternoon or evening—shop here, duck into a bar there, challenge a stranger to a curling match at the next spot. There’s worse ways to spend a Saturday in December than hopping to as many bedazzled barrooms as you and your pals can muster.

Or simply see how many larger than life decorated Christmas trees you can find. Here’s a head start..Millenium Park, Macys, Daley Plaza, Gallager Way, Bloomingdales, Lincoln Park Zoo, etc.

Keep reading with a 7-day free trial

Subscribe to Flags Candy Wine to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2025 Ryan Maconochie
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share