1. Christkindlmarket: Everyone's favorite holiday market is back in Daley Plaza. Kids can sip on adorable snowman mugs filled with hot chocolate and participate in events through the Kinder Club. (Daley Plaza, Washington and Dearborn Streets. Through Dec 23: Sun–Thurs 11am–8pm; Fri, Sat 11am–9pm. Free.)
2. Ice Skating: It's officially skating season in Chicago, so lace up your skates and hit the rink at nearly a dozen indoor and outdoor spots around the city. (Various locations across the city.)
3. Illumination: Tree Lights at Morton Arboretum: Stroll through the mile-long path to admire dancing lights set to the Chicago Symphony Orchestra's recording of The Nutcracker at this scenic holiday tradition. (Morton Arboretum, 4100 Illinois Rte 53, Lisle, IL. Through Jan 2: Daily at 5pm. $7–22.)
4. A Christmas Carol: Skip the bah humbugs, the Goodman Theatre's holiday hit returns for its 39th year of spinning the classic Dickens tale on stage. (Goodman Theatre, 170 N Dearborn St. Through Dec 31 at various times. $25–102.)
5. The Nutcracker: Apparently Chicago really, really loves The Nutcracker. This holiday season take in more than a dozen iterations of the classic tale, including the Joffrey Ballet's world premiere set at the 1893 World's Fair. (Various locations across the city.)
6. Caroling at Cloud Gate: Local choral groups lead the way in this caroling turned sing-a-long on Friday nights at Millennium Park. Catch a glimpse of Santa Claus before the singing starts and hit the ice rink afterwards. (Millennium Park, 201 E Randolph St. Through Dec 16: Fri at 6pm. Free.)
7. Juicebox Series: This pre-lunchtime event is designed to get your kids' creative juices flowing. (•Chicago Cultural Center, 78 E Washington St. Dec 2 and 16 at 11am. Free. •Garfield Park Conservatory, 300 N Central Park Ave. Dec 3 at 11am. Free.)
8. Winter WonderFest: Enjoy all of the best winter activities indoors at Navy Pier's annual holiday carnival. (Navy Pier, 600 E Grand Ave. Dec 2–Jan 8: Mon–Thu 10am–8pm; Fri, Sat 10am–10pm; Sun 10am–7pm. General admission $10; activity tickets $25.)
9. Cinderella at the Theater of Potatoes: The Hypocrites whip up an alternate take on the Cinderella story with elements from the 1904 operetta Cendrillon and other works in the freewheeling style the theater is best known for. (The Den Theatre, 1329–1335 N Milwaukee Ave. Dec 2–Jan 8 at various times. $36, students $15.)
10. The Annoyance Christmas Pageant: The Annoyance's annual kid-friendly show puts a spin on holiday classics A Charlie Brown Christmas and Rudolph the Red-Nosed Reindeer for a night kids and parents can enjoy together. (Annoyance Theatre, 851 W Belmont Ave. Through Dec 23: Fri at 8pm. Dec 4 at 3pm. $20, kids under 12 $14.)
11. The Sound of Music Sing-A-Long: The hills are alive and the whole family can join in the fun of this annual sing-a-long held at the Music Box. Guests regularly come in costume, so it might be time to bust out the lederhosen. (Music Box Theatre, 3733 N Southport Ave, Dec 3, 4 at 11:30am. $12.50, $8 for kids.)
12. Holiday Magic at Brookfield Zoo: Get in the holiday spirit and sing carols to the animals while enjoying the festive lights and decorations throughout the zoo. Enjoy special activities, magic shows, a model railroad and more. (Brookfield Zoo, 8400 31st St, Brookfield, IL. Through Dec 18: Sat, Sun at 4pm. Dec 26–31: Daily at 4pm. $17, children (3–11) $12.)
13. A Charlie Brown Christmas: The whole Peanuts gang is back onstage in Emerald City Theatre's production to remind us all about the true meaning of Christmas. (Broadway Playhouse, 175 E Chestnut St. Dec 3–Jan 8: Various days at 10am. $18-$39.)
14. That's Weird, Grandma: The Barrel of Monkeys troupe conducts writing workshops with CPS grade school students during the day and then transforms those stories into skits and songs for all to enjoy. The public show goes holiday-themed for the month of December. (Neo-Futurarium, 5153 N Ashland Ave. Through Dec 26: Mon at 8pm; Sun at 3pm (no show Dec 25). $12, kids under 12 $6.)
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