The Ultimate Holiday Checklist: 25 Things to Do in Chicago
May your days be merry and bright
We'll admit we’ve gotten lost in all the holiday hustle and bustle, only to wake up in January. Take a few minutes to slow down and look around, and you’ll see that there are a million fun things to do around the city this time of year. We’ve picked 25 of the best holiday shops, shows, museums and restaurants to get you started.
1. Savor a massive Bavarian pretzel, listen to an Alpine brass band and shop for handmade ornaments at Chriskindlmarket in Daley Plaza (through December 24).
2. Take advantage of the awesome free stuff at Randolph Street Market’s final holiday market: free gift wrapping, free trolley service from Water Tower Place and—yes—free pet portraiture.
3. You never thought you’d see the Marshall Field’s Macy’s windows dedicated to the Chicago Cubs’ “W” (through January 17). So take it all in and then head indoors to see the massive tree and eat potpie in the Walnut Room.
4. Head to the Bridgeport Art Center for the ultimate in handmade wares at the Renegade Craft Fair (December 3 and 4). Artisanal perfumes, leather goods and jewelry make much more memorable gifts than your standard mall fare.
5. Find a gift for the person who has everything at Lakeview’s Foursided. Between the handmade cards, artwork and jewelry, you’ll become the best gift giver in the city.
6. Update your requisite viewing of The Nutcracker by snagging tix to Tony Award-winning choreographer Christopher Wheeldon’s twist on the classic at the Joffrey Ballet (through December 30). Hint: It all takes place at Chicago’s 1893 World’s Fair.
7. Join the tradition of seeing A Christmas Carol at The Goodman (until December 31). The classic Charles Dickens tale of holiday loss and redemption has been a seasonal production here since 1978.
8. For something a little more cynical, head to Theater Wit for This Way Outta Santaland (through December 23), a raucous adaptation of the hilarious David Sedaris essay about toiling as a holiday elf at the Macy’s flagship store in Manhattan.
9. Belt out some tunes at a double feature of White Christmas and It’s a Wonderful Life at the Music Box Theatre for its 33rd annual Christmas double feature and sing-along (from December 10 to 24).
10. Satisfy even more cinematic nostalgia with the Logan Theatre’s December lineup. From Die Hard to Home Alone, there’s something for everyone.
12. See how the Swedes celebrate at Andersonville’s St. Lucia Festival of Lights on December 13. The evening begins with a candlelit, carol-filled walk down Clark Street, followed by more caroling and regional treats (we hope there are ginger snaps!) at the Swedish American Museum.
13. Test out the Maggie Daley Skating Ribbon (open through the first week in March, weather permitting). With a length twice that of a lap around a traditional rink, it winds through a rolling landscape dotted by trees and views of the Chicago skyline.
14. Before or after your laps on the Maggie Daley Skating Ribbon, stop by Millennium Park to visit with Santa (weekends through December 18) or do some caroling by Cloud Gate, aka “The Bean” (Fridays through December 16).
15. Be a tourist in your own city on the Chicago Trolley Holiday Lights Tour, which starts at the John Hancock Center, tools down the Magnificent Mile and ends at Lincoln Park Zoo for its ZooLights display.
16. Speaking of ZooLights, check the calendar of the annual lights display for special events through its final date on January 1. There’s an adults-only night on December 7, live music inspired by A Charlie Brown Christmas on December 15 and even a New Year’s Eve celebration.
17. Discover how 50 countries celebrate the winter holidays at the Museum of Science and Industry’s Christmas Around the World exhibit (through January 8) or just stop in anytime for a magical indoor snowfall every half hour.
19. Head to RPM Italian on Christmas Eve for a traditional Feast of the Seven Fishes, an abundant meal of chilled seafood salads, handmade pastas, whole-roasted fish and desserts.
20. Kick back after a day of shopping with high tea at the Langham. The holiday menu includes spiced gingerbread molasses cake and an icy peppermint eggnog.
21. Eat alllll the cookies at the charming Ferrara Bakery in Little Italy.
22. Drink a big mug of glogg (Swedish mulled wine) at the famous Simon’s Tavern. (Even Anthony Bourdain had to stop there on his show The Layover.)
23. Walk down Lincoln Avenue in Roscoe Village and you’ll smell Dinkel’s Bakery before you see it. Step inside to order a perfect yule log from the nearly century-old bakery.
24. Sip one of Chicago’s best martinis beneath a ceiling hung with hundreds of handmade snowflakes in the former speakeasy Club Lucky.
25. Grab a seat near the upstairs balcony at Le Colonial to watch the snow fall on passing shoppers on Rush Street. The restaurant’s menu of French-Vietnamese fare will fuel you for an afternoon of shopping in the stylish neighborhood.