How to Celebrate the Holidays in Chicago This Year

These are the best ways to spend the most wonderful time of the year.

The holiday season is here in force, if you couldn’t tell from the fact that we’ve already had our first snow of the winter and all of the festive lights. The bad news is that means that those balmy 40 degree autumn days are gone. The good news is that our fair city has more than enough fun activities (both indoor and outdoor) to help you celebrate the holiday season in style.

Bring some holiday cheer home at one of Chicago’s Christkindlmarkets

The Christkindlmarket, Chicago’s best and largest holiday marketplace, has expanded and now boasts three locations: one in Aurora, one in Wrigleyville, and its flagship location downtown. All three will feature the traditional holiday handcrafts, sausages, pretzels, and Glühwein the market is known for, along with live music and entertainment. It’s a holiday tradition for a reason.

Bounce into the spirit of the season with some balloon art

Luft Balloons Chicago has given its Wicker Park retail location a holiday makeover, and is allowing visitors of all ages to come in and tour their balloon-filled Santa Wonderland. Employees will be on hand to help visitors snap the perfect selfie among the balloon art (a highlight is the balloon Santa), and your time there will also include a scavenger hunt and a discount on any balloon art you’ll want to pick up for your own holiday celebration.

Bathe in nostalgia with jazz covers of holiday classics

Streeterville’s favorite jazz destination Winter’s Jazz Club is getting in the spirit this year with a selection of holiday-themed shows up until Christmas, including a jazz trio tribute to A Charlie Brown Christmas, as well as a Christmas-Eve-Eve celebration featuring soulful covers of holiday classics. Tickets are available now, so dust off that fedora you bought in 2009 and have yourself a jazzy little holiday.

Celebrate eight crazy nights

However you spell it, Hanukkah usually gets the short end of the stick when it comes to holiday pop-ups and celebrations. Thankfully, Wrigleyville’s Graystone Tavern offers a welcome alternative to Santa Baby with their 8 Crazy Nights pop-up. Snap some photos at their ugly Hanukkah sweater wall, indulge in their boozy spin on classic sufganiyot (jelly-filled donuts), and round up a group of friends to perform what can only be referred to as a “menorah shotski.” Chag sameach.

Courtesy of Chicago Botanic Garden

Immerse yourself in twinkling lights

By far one of the most romantic activities you can do this holiday is take someone special to the Chicago Botanic Garden for their newly revamped holiday lightscape. Walk the path through the gardens and take in the art installations, including the fire garden and the classic Winter Cathedral. There are few better ways to take in the magic of the holiday than among the lights.

Experience a re-imagined holiday classic at The Marriott

Running through January 1, The Marriott Theatre is currently featuring a musical adaptation of A Christmas Story—adapted by the minds behind Dear Evan Hansen, La La Land, and The Greatest Showman. Why not celebrate the season with a show, let alone a show nominated for three Tony awards, including Best Musical? Tickets are available now, though availability is dwindling for certain show dates.

Have a headbanging holiday

A mainstay in any holiday playlist worth its salt, the Trans-Siberian Orchestra is playing back to back shows at Allstate Arena featuring their trademark metal arrangements of holiday classics. Pull those leather pants out of your closet and start growing your hair out now, because the shows are coming up soon.

Lace up your skates and take to the city

There’s no shortage of ice rinks in Chicago to show off your skating skills. On Ice, from the indoor McFetridge Sports Center to the rink at Millennium Park. Our favorite spot to skate, however, is The Ribbon at Maggie Daley Park, a winding loop that features some of the best views of the skyline. Take your pick, and then drop into a cafe to warm up with some cocoa. Holiday bliss.

Snap a selfie with the city’s official Christmas tree

Make the trek downtown to the corner of Michigan and Washington to bask in the glory of Chicago’s official Christmas tree, a 55-foot Colorado Blue Spruce. Although the lighting ceremony was back in November, the tree itself will be on display through early January, complete with painstakingly-placed decorations, lights, and ornaments. If you’re by the Magnificent Mile doing your holiday shopping, make it a point to stop by.

Get classy at the ballet

Depending on how your end-of-year finances shook out, taking part in one of Chicago’s best holiday traditions is a great way to ring in the season. The Joffrey Ballet, one of the world’s premier dance companies, is running their yearly production of The Nutcracker through December 27. And despite what you might think, it’s actually not that pricey to go see the show! Tickets start at $64 for weeknight shows, which is approximately the cost of a Grubhub Cheesie’s order for two.

Watch a holiday classic on a REALLY big screen

Pilsen’s ChiTown Movies has been keeping the drive-in film tradition alive since they opened, and they’re showing holiday classics all month, from Die Hard, to A Muppet Christmas Carol, to a Christmas Day showing of Home Alone. Enjoy the drive through the snowy city, crank your heat up, and celebrate the season from the comfort of your own car.

Traipse through a gigantic winter wonderland

A huge swath of Goose Island has been transformed into a holiday winterscape, courtesy of Jack Frost Winterfest. Play hooky for a day and indulge in some axe throwing, ice skating, and drinks courtesy of multiple full bars—and then wander through the Christmas tree farm to pick out a seasonal souvenir from your visit. These Goose Island pop-ups never disappoint, so make sure to check it out.

Brave the cold for a themed holiday run

The Hot Cocoa Hustle might be behind us, but for Chicago runners, there are still plenty of winter runs to take part in. Our recommendation is the officially licensed Charlie Brown Christmas run, a virtual race that you can complete on your own schedule. Bibs are available for 5ks, 10ks, and a 13.1 mile challenge—and include a bunch of themed swag including a beautiful hand-painted finisher medal.

Have a snow-free snow day at the Garfield Conservatory

For those of us who love winter, but hate what it does to Chicago’s vibrant plant life, Garfield Conservatory has you covered. Their winter flower show is currently open, themed after the feeling we all got as kids when we woke up and school was canceled due to snow. The exhibits will feature geraniums, poinsettias, pansies, and more in evocative arrangements of pink and white, evoking the fluffy, comforting textures of snow in the sun. As an added bonus, the delightful scents should be enough to break through even the sniffliest of sinuses.

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Sam Greszes is a contributor for Thrillist.