Monday, December 14

Eat dessert first at Toothache, a celebration of holiday pastries hosted by Two (1132 W. Grand Ave., West Town, 312-624-8363). Eleven sugar pros from spots such as Cindy’s, MK, and Bohemian House will descend on the restaurant to share their own wintertime treats. Attendees get to nibble on each and pick a favorite starting at 5 p.m., with a winner to be crowned at the end of the night. Tickets are $45, and you’re encouraged to bring toys and winter clothing to donate to underprivileged kids in the area.

Tuesday, December 15

Skip the ugly Christmas sweater for the holiday party at the Bar on Buena (910 W. Buena Ave., Uptown, 773-525-8665). They’ve teamed up with Begyle Brewing for the occasion, and they’ll have several of the outfit’s beers available to drink, including a nitro version of the Freebird Pale Ale. The dress code for this event? Ugly pajamas—bring out your flannel finest. The festivities start at 7 p.m.

Get cooking at a holiday demonstration at Mercadito (108 W. Kinzie St., River North, 312-329-9555), where you’ll be shown how to make five different courses as you sip on five paired seasonal beverages. The $60 demo starts at 6:30 p.m. Call the restaurant to make a reservation.

Thursday, December 17

There are lots of enticements to order lunch from a Lettuce Entertain You restaurant using meal-delivery service UberEATS today. If you select a meal from RPM Italian, RPM Steak, Bub City, Hub 51, R.J. Grunt’s, or Ramen-San, you’ll take part in the #LettuceGive campaign, and all proceeds from your meal ordered between 11 a.m. and 2 p.m. will go to the Greater Chicago Food Depository. To top it off, you’ll also get a $10 gift certificate to whatever restaurant you ordered from. You can access the promotion through your Uber app—just open it and press the icon with a plate and forks to get your food.

Saturday, December 19

Deck the gingerbread halls at a housemaking party at Ceres’ Table (3124 N. Broadway, Lake View, 773-922-4020). For $22, you’ll get your own structure to decorate along with plenty of hot cocoa to drink, and there will also be a visit from a holiday elf for kids. (Adults can sip on some very grown-up egg nog.) Call the restaurant to get in on the action.