Caroling at “Cloud Gate” in 2019. (Courtesy of the Chicago Department of Cultural Affairs and Special Events)
1. Belt
Spread some holiday cheer at three caroling events. The Millennium Park Holiday Sing-Along returns for the season with Windy City Performing Arts leading the charge. The 40th annual Music Box Christmas Sing-A-Long & Double Feature kicks off this weekend with screenings of “White Christmas” and “It’s a Wonderful Life.” Santa welcomes the audience to each show, and organist Dennis Scott leads the crowd in Christmas carols with lyrics projected onto the screen. At the Old Town School of Folk Music, Songs of Good Cheer celebrates its 25th anniversary; songbooks will be provided, and a portion of proceeds benefits the McCormick Foundation Communities Fund.
Details for the Millennium Park Holiday Sing-Along: 6 p.m. Friday at Wrigley Square at Millennium Park, 201 E. Randolph St. Free / MAP
Details for the Christmas Sing-A-Long & Double Feature: Times vary Friday through Dec. 24 at the Music Box Theatre, 3733 N. Southport Ave. $12-21 / MAP
Details for Songs of Good Cheer: Times vary Thursday to Sunday at Old Town School of Folk Music, 4544 N. Lincoln Ave. $52-54 / MAP
Looking for more events? Check out the season’s light shows, markets, performances and pop-ups in our 2023 Chicago Holiday Events Guide.
2. Imagine
Pocket Con is a single-day convention for youth that celebrates diversity with a focus on artists and characters of color. Coinciding with Family Day at MCA Chicago, this year’s event includes workshops, cosplay contests, a marketplace and panel discussions.
Details: 10 a.m.-4 p.m. Saturday at the Museum of Contemporary Art Chicago, 220 E. Chicago Ave. Free / MAP
Pocket Con. (Elgin Smith)
3. Connect
Celebrate the Festival of Lights at the Hanukkah Candle Lighting & Drag Queen Storytime. The event includes cozy winter drinks, a menorah lighting and family-friendly songs and stories from Drag Bubbie Merriam Levkowitz.
Details: 4 p.m. Sunday at The Understudy Coffee and Books, 5531 N. Clark St. Free / MAP
4. Marvel
Magician Jamie Allan returns to Chicago with his new show “Amaze.” The English performer blends technology and timeless techniques and invites audience members to partake in the performance.
Details: Showtimes vary through Jan. 7 at Rhapsody Theater, 1328 W. Morse Ave. $30-100 / MAP
5. Hunt
Find gifts for everyone on your list this weekend. The One of a Kind Holiday Show features more than 500 artisans and makers in categories ranging from fine art to gourmet goods; expect live music from the Old Town School of Folk Music and free workshops from Marwen. At The Plant Holiday Market, you’ll find everything from local honey and bath bombs to houseplants and barrel-aged beer; Whiner Beer Company is offering a free brewery tour. The Trashy Holiday Market, which spans three locations, bills itself as a junky jamboree; shop upcycled and hand-crafted wares including home goods, planters and art. For an evening experience, head to the Sauced Night Market Before Xmas for local vendors, craft cocktails and a live DJ.
Details for One of a Kind Holiday Show: 10 a.m.-7 p.m. Thursday to Saturday, 10 a.m.-5 p.m. Sunday at The Mart, 222 W. Merchandise Mart Plaza. $15-25 / MAP
Details for The Plant Holiday Market: 11 a.m.-3 p.m. Sunday at The Plant, 1400 W. 46th St. / MAP
Details for The Trashy Holiday Market: 1-5 p.m. Sunday at three locations: Ignite Glass Studios, 401 N. Armour St. (MAP); Patagonia x Worn Wear, 1115 W. Fulton Market (MAP); and District Brew Yards, 417 N. Ashland Ave. (MAP) Free
Details for the Sauced Night Market Before Xmas: 5-10 p.m. Friday and Saturday at the Chicago Athletic Association, 12 S. Michigan Ave. Free with RSVP / MAP
(Courtesy of One of a Kind Show)
Events listed are subject to change. We recommend double-checking times and locations before you head out the door. Want to share your upcoming events with us for consideration in a future roundup? Send us an email.
