1 Your jingle balls will shiver as you kick off a month of merriment by dashing through Halsted Street for charity in nothing but a Santa hat and skivvies at the second annual Most Fabulous Santa Speedo Run (2pm, sidetrackchicago.com).
2 Enjoy smooth sounds with queer melody makers Lakeside Pride at the annual Jazz Band Holiday Concert (7:30pm, callbarchicago.com).
3 Make Monday a fun day with a viewing of Scrooge & Marley, a queer (and Chicago-based) retelling of A Christmas Carol (7:30pm, musicboxtheatre.com) starring lots of local actors and familiar faces.
4 Decide whether you’re naughty or nice at Nuts & Bolts: A DIY Dance Party (9pm, Township), where this year’s “A Luminaughty Ball” aims for winter masquerade glamour.
5 While shoppers shiver, relax indoors with the seasonally brewed Mary Christmas Ale at the Rec Room at Hamburger Mary’s (hamburgermarys.com).
6 Booze it up with the Lambda Legal Chicago Leadership Council at its second annual Holidays on Ice happy hour party at Downtown Lounge (6pm, lambdalegal.org).
7 Spend Christmas with the Joans as the Crawford look-alike band cranks out holiday merriment at Jackhammer (9pm, fleshhungrydog.com).
8 Spin the dreidel at Touché’s Chanukah Party with Chanukah Harry and enjoy games, gelt and gifts plus $2 Manischewitz wine and $5 Jewbelation HeBrew beer (10pm, touchechicago.com).
9 Hit Hyde Park with the members of Chicago Gay Men’s Chorus as they Make the Yuletide Gay (7:30pm, cgmc.org) with an evening of seasonal sounds.
10 Enjoy an evening of soulful holiday classics with a most fabulous (and gay-fronted) cabaret trio at Foiled Again’s Annual Holiday Show in Evanston (7:30pm, evanstonspace.com).
11 Warm up with not one, not two, but a dozen seasonal martinis at Call bar at its monthlong 12 Absolut Martinis of Christmas (callbarchicago.com).
12 Take a very merry walk down Halsted Street and marvel at more than 20 fabulous window displays (including Beatnix, Sidetrack, I.D.) at the Northalsted Holiday Window Walk, whose theme this year is “A Curious Holiday on Halsted” (northalsted.com).
13 Have A Very Merry Christmas as Drag Race star Mimi Imfurst portrays the Virgin Mary in her one-night-only holiday show (9:30pm, hydratechicago.com).
14 Stroll the strip and have your pic taken with Santa at Late-er Night Andersonville, an evening of after-hours shopping and holiday festivities (6–10pm, andersonville.org).
15 It’s a Festivus for the rest of us at Crew’s annual Festivus Customer Appreciation Party, where you can air your grievances and have your picture snapped with the Festivus Pole (7pm, worldsgreatestbar.com).
16 Enjoy a hand-crafted cocktail to the sounds of Phil Collins, Hall & Oates and other lite-rock giants at the holiday edition of Jyl Fehrenkamp’s Soft Rock Sabbath (9:30pm, whistlerchicago.com).
17 Queer up Millennium Park by hitting the McCormick Tribune Ice Rink for a night of skating. Lines can be murder, but you may have better luck on a weekday (Noon–8pm, explorechicago.org).
18 Gay, straight, bi or whatever, everyone loves the 1983 holiday classic A Christmas Story. It screens tonight along with director Bob Clark’s other yuletide tale Black Christmas (TBA, musicboxtheatre.com).
19 Expect a ski lodge vibe and hot toddies galore at Burly (9pm, theburlingtonbar.com), a night for bearded men and their admirers.
20 San Francisco’s draggy and hilarious a cappella quartet, the Kinsey Sicks, returns to charm us yet again with Oy Vey in a Manger (7, 9:30pm; maynestage.com).
21 You can’t escape the season without the perverted theatrical stylings of MidTangent Productions, which returns to Hydrate with Christmas doubleheader Santa’s Dead and Dirty Carol’s Christmas (9pm, hydratechicago.com).
22 What happens when you make a Christmas wish and end up with a pop diva instead? Holiday hell breaks loose when Liza Minnelli drops in on Conrad Ticklebottom in About Face Theatre’s We Three Lizas (3, 7pm; steppenwolf.org).
23 Classic holiday films and over-the-top martinis (Frosty’s Going Down, anyone?) rule at Kit Kat’s Jingle Bells Brunch starring Diva Madame X (11am–3pm, kitkatchicago.com).
24 Still feeling naughty? Hit Touché’s Christmas Eve Party (10pm, touchechicago.com) featuring holiday drinks and goodies (we’re guessing edible and fleshy).
25 If you’re far away from your loved ones (or not on speaking terms with them), a hot meal and community of support await at the Center on Halsted’s free Christmas Dinner (noon, centeronhalsted.org).