The Chicago winter can be a magical place to spend the holidays so don’t be a bore and spend it indoors. If you’re not sure what to do this holiday season we’ve got some ideas for you.


1.The Skating Ribbon @ Maggie Daley Park

Peanuts snow charlie brown snowing ice skating

Ice skating with your beau could be the most classic holiday event there is. Skating hand in hand around the ribbon with the city skyline in the background is the perfect holiday date idea. You can try recreating the uber sentimental scenes from Elf, Serendipity, or any of the other holiday RomComs. Don’t have a special someone, don’t worry, go with a group of friends and have fun making fun of the cheesy couples skating hand in hand. You could even trip them if you’re feeling a little extra cynical that day. The ribbon is open until March and admission is free, you only have to rent the skates.

2.Visit the Christkindlmarket

The market which is a millennial since it was started in 1995 is inspired by a 16th-century holiday market tradition from Germany. The market has vendors that make handmade toys and trinkets that make perfect gifts for friends and family. The market also sells food and more importantly german beer and Glühwein, a german spiced wine that comes in a souvenir boot mug. The wine, I mean market, could make any grinch’s heart grow three sizes. The market is open every day until December 24th.

3. Throw an Ugly Christmas Sweater Party

GIPHY Studios Originals christmas holidays happy holidays ugly sweater

Our generation loves a good theme party and what’s the perfect theme for the holidays: Ugly Christmas Sweater! It’s a super simple theme, go to any store or thrift shop and you’ll be sure to find an obnoxiously hideous Christmas sweater. After you just perfect the sweater all you need to do is invite some friends over and buy some booze, maybe eggnog, but who likes that. The party will be a complete success because it has the three key elements to a perfect party, a theme, good company, and booze!

4. See the Zoo Lights

elf nightmare before christmas christmas gif nightmare before xmas nightmare before christmas gif

The Lincoln Park Zoo lights is a quintessential part of the Chicago holiday season. Talk about making spirits bright, the zoo puts up more than two million lights that will transport you into a magnificent winter wonderland. The lights will definitely give you the warm and fuzzies inside and so will the fact that it’s completely free.

5. See The Nutcracker

ADWEEK dancing christmas commercial ballerina

If you’re one of those artsy types or you want to be one of those artsy types The Joffrey Ballet’s The Nutcracker should be on your holiday to-do list. What’s even better about this year’s version is that Tony Award-winning choreographer Christopher Wheeler has reinvented the classic story and reset it during the 1893 World’s Fair in Chicago. Now, what could be better for a Chicago Ballet lover than a loved ballet set in Chicago? Performances start the 10th of December through December 30th.

6. Winter Pub Crawls and Libation Tastin’ Festival

christmas beer drunk holiday sleeping

For the 21 and over crowd Chicago hosts a number of holiday pub crawls and a wine, spirits, and beer festival. The holidays are a stressful time, all of that holiday shopping and spending time with family can really take a toll on your psyche. Why not lift your spirits with some spirits or another kind of alcoholic beverage. The crawls include: 12 Bars of Xmas TBOX Pub Crawl, Chicago Running of the Santa’s Pub Crawl, and Chicago Christmas Crawl through Old Town. Not a pub crawl person try going to the Libation Tasin’ Wine, Spirit and Beer Festival.

7. Go to Winter Wonderfest @ Navy Pier

night chicago

I know what you’re thinking, why the hell would I want to go to Navy Pier? The truth is you don’t but your family or visiting friends probably will. Winter Wonderfest is a perfect place to take them because not only is it at probably the most overrated Chicago Tourist attraction but it’s also very festive. The Wonderfest has ice skating, music, and other entertainment perfect for everyone in your family. Even better, it’s indoors so you won’t have to whether the frigid weather.

8. Bring in the New Year @ Chi-Town Rising

2016 lea michele happy new year new year new years eve

Don’t have the money to travel to NYC to see the ball drop, probably not you’re a millennial, next best thing, Chi-Town Rising. It’s Chicago’s very own version of Time Square New Year’s celebration and ball drop, except, it’s a rising star instead of a dropping ball. The event has live music, celebrities, fireworks, and of course a rising star.