12 Nice, Naughty and New Ways to Celebrate the Holidays in Chicago

If your favorite holiday traditions are starting to feel more ho-hum than ho-ho-ho, we’ve got 12 unexpected activities to put on your seasonal checklist, from an edifying tea service to an epic sundae.

8 Winter Coats That Aren’t Just Another Black Puffer

rudolph reboot
Nikki Loehr

The New: Rudolph Reboot

We could all use a laugh around the holidays. Luckily, the Annoyance Theatre is at the ready with its annual Christmas Pageant (November 10 through December 23). The cast puts a hilarious and kid-friendly spin on two holiday classics: A Charlie Brown Christmas and Rudolph the Red-Nosed Reindeer.

skydeck santa
Skydeck Chicago

Santa At Willis Tower

When visiting Santa at the mall won’t do, head 1,353 feet up in Willis Tower. Old Saint Nick will be visiting the Ledge from December 20 to 23. Stop in to snap a quick selfie or pose for a holiday picture that’s just the tiniest bit extra.

turkey chicago
Christina Slaton

Southern Thanksgiving

Break with your roasted turkey tradition. Bub City’s Southern-inspired smoked turkey comes with mashed potatoes, gravy, stuffing and “sweet tater fluff.” The delicious feast serves eight and costs just $30 per person.

millers pub
Pawel Skrabacz

Drinks, Daleys And Dead Guys

Discover how Mayor Richard J. Daley saved the Christmas Parade on this quirky (and mostly indoor) walking tour. You’ll also get to enjoy a hot Tom and Jerry cocktail at historic Miller’sPub and take in views of the Chicago Christmas Tree in Millennium Park.

chicago design market
Chicago Design Market

The Nice: Gifts With A Twist

What’s better than shopping small? Shopping one-of-a-kind. Doing so is all too easy between the Chicago Design Market, Randolph Street Holiday Market, One of a Kind Show and Chicago Artisan Market. With food, drink, music and plenty of people watching at each, the act of buying gifts is almost as fun as receiving them.

hanukka the gold coast
Zach Dobson

Hanukkah In The Gold Coast

When the festival of lights kicks off on December 2, 20 East at the Talbott Hotel will be celebrating with daily specials like grilled beef brisket with romesco, cippolini onions and hazelnuts. Best of all, it’s smack dab between Chicago Sinai Congregation and Sprinkles Cupcakes, where you can get Hanukkah-decorated treats.

open books chicago
Ashley Lane

Give The Gift Of Reading

There are many ways to volunteer with literacy nonprofit Open Books Chicago, but all of them celebrate a love of the written word. Get buddied up with school-age kids to work on reading or writing skills. If you’re more comfortable behind the scenes, you can donate books or help with sorting and shelving in the bookstore.

tea with history chicago
Joshua Ferguson

Holiday Tea With A Side Of History

Booth One takes your standard holiday tea service and does you one better. From November 29 to December 8, historian Sally Kalmbach will guide you through the lives of the civic-minded and entrepreneurial women of Gilded Age Chicago, while you snack on tea sandwiches and seasonal scones ($42 per person).

christmas commiseration drink
Lyndon French

The Naughty: Christmas Commiseration

If you’re of the mind-set that Christmas sucks, join your fellow grinches at Ludlow Liquors. Starting November 29, they’ll be taking the holiday cheer down a notch with creepy Christmas decor, tragic family holiday photos and a special menu of “not eggnog” all month long.

elf spaghetti chicago
Virgin Hotels Chicago

Eat Like An Elf

Ready for a sugar binge? In honor of Elf’s 15th anniversary, Miss Ricky’s at Virgin Hotel will dish out a sundae inspired by Buddy the Elf’s spaghetti breakfast. Yep, the recipe calls for spaghetti—along with strawberry and raspberry sauce, marshmallows, s’mores Pop-Tarts, M&Ms, Oreos, Fruity Pebbles, coconut and chocolate sauce. (C’mon, you know you kind of want to try it.)

christmas mugs chicago
Santa Baby

Pair Cocktails And Cookies

Sorry, milk, but we’d much rather pair our cookies with boozy hot chocolate. Santa Baby, an over-the-top Christmas-themed bar, opens November 21 in Wrigleyville with wall-to-wall Christmas decor, an appropriately festive drink menu, outdoor s’mores fire pits and appearances by Santa and friends until January 6.

pizza party chicago
Chicago Pizza Museum

Pizza Party

When in doubt about how to celebrate the holidays, honor pizza, everyone’s favorite food. The U.S. Pizza Museum at Roosevelt Collection is extending its stay, so there’s more time to check out the rare pizza boxes, vintage ads, toys, video games and more. Pro tip: Stop in onSaturday, December 15 at 7 p.m. for a viewing of Home Alone

amanda nyren

Writer, yogi, mom to about a dozen houseplants

A lifelong Chicago resident, Amanda started covering the local scene for PureWow in 2016. She's a freelance writer and content strategist.