How to Make the Most of 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.

Indoor Holiday Things to Do in Chicago

Saturday, December 2-Wednesday, December 27
Downtown, $36+
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 $36 for weeknight shows, which is essentially what you’d be paying for that one-person food delivery order anyway.

Sunday, December 3
West Loop, $83+
Celebrate Mariah Carey’s yearly return in person at the United Center with a concert. We have it on good authority that there’s a slim, outside, miniscule chance she might play “All I Want for Christmas is You,” so cross your fingers. Tickets start at $83.

Sunday, December 10
Des Plaines, $25+
A mainstay in any holiday playlist worth its salt, the Trans-Siberian Orchestra is playing a show at the Des Plaines Theater 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 show is coming up soon.

Now through January 7
Wrigleyville, Cost varies
Wrigleyville’s Graystone Tavern is offering a welcome alternative to Santa Baby with their Eight 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.”

Sunday, November 26
Downtown, $49+
Shake off that post-Thanksgiving hangover and hop downtown to the Chicago Theatre for a screening of National Lampoon’s Christmas Vacation, complete with a Q&A session featuring Chevy Chase himself. Chase and his wife Jayni Chase will be there to dish on behind-the-scenes antics from filming the movie, as well as fielding questions from the audience on his entire career. There are even photo ops available for particularly rabid fans of his body of work.

Courtesy of Chicago Botanic Garden

Outdoor Holiday Things to Do in Chicago

Ice skating

All winter
Various locations, Cost varies
There’s no shortage of ice rinks in Chicago to show off your skating skills—from the indoor McFetridge Sports Center to the rink at Millennium Park. Don’t miss The Ribbon at Maggie Daley Park, though, a winding loop that features some of the best views of the skyline. Just be aware that you’ll have to reserve your time in advance. Take your pick, and then drop into a cafe to warm up with some cocoa. Holiday bliss.

Friday, November 17-Thursday, January 7
Downtown, Free
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. The lighting ceremony takes place on November 17 at 6 pm, and 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.

Friday, November 17-Sunday, December 31
Downtown, Aurora, Wrigleyville, Cost varies
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.

Through the holiday season
Various locations, Cost varies
By far one of the most romantic activities you can do this holiday is take someone special to the Chicago Botanic Garden for their 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.

Thursday, November 30-Sunday, December 31
Fulton Market, Cost varies
A huge swath of Fulton Market has been transformed into a holiday winterscape, courtesy of Jack Frost Winterfest. Play hooky for a day and indulge in some ax 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 pop-ups never disappoint, so make sure to check it out.

Through Sunday, December 31
Anywhere, $50+
The Hot Cocoa Hustle might be behind us, but for Chicago runners, there are still plenty of winter runs to take part in, like the officially licensed Charlie Brown Christmas run, a virtual race that you can complete on your own schedule. Entries are available for 5K and 10K distances—and include a bunch of themed swag including a beautiful hand-painted finisher medal.

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Sam Greszes is a contributor for Thrillist.