Eat, Drink & Be Very Merry In Chicago This Holiday Season

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Forget the 12 days of Christmas, Windy City residents have more than twice that amount of time to indulge in holiday treats, festive eats and spirited drinks throughout November and December.

Eat
Entrepreneur Susan Sarich grew up in Chicago near her grandmothers Mildred and Madeline who would serve her homemade desserts everyday after school. Decades later their recipes inspired Sarich to open SusieCakes bakeries on the West Coast. Created in 2006 to help people commemorate special moments, the female-owned bakery chain offers a 4-layer vanilla Celebration Cake which became a favorite for the rich and famous (Demi Lovato, Jennifer Garner, Jessica Simpson, the Kardashians, and Reese Witherspoon).

Enhance your festivities with the signature SusieCakes Celebration Cake ($89 incl. shipping) and a Rebellious logo coffee cup ($19.95).

Now, Chicagoans can add their names to this celebrated customer list since the successful franchise offers nationwide shipping. Delivered in recyclable packaging, the retro-inspired dessert serves 6-12 people.

In addition to donating a part of its proceeds to the Red Cross and various animal shelters, the nearly 85% female-led company has given more than $4 million in baked goods to veteran’s groups, food banks, homeless shelters and women’s domestic abuse safe houses. 

Lillstreet Art Center marks a milestone with its 50th Anniversary Holiday Party (Dec. 5). The family-friendly event includes complimentary food and drinks, live music, art workshops, open studios, a free art demo, and The Holiday Table–a gallery show featuring ceramics, jewelry, textiles and other gift items by more than 50 craft artists from the Lillstreet community and around the country.

“When I started Lillstreet back in 1975, my intention was to teach art, provide a space for working artists, and be a center of art education for a diverse group of communities. And while we’ve grown from 8,000 square feet on Lill Street to 40,000 on Ravenswood Avenue, and from six classrooms to 27, we are still as much about building communities as about making art; that has never changed. We are a serious art center, but we are also a relaxed, non-competitive, and friendly community center. This combination is what I believe makes Lillstreet a unique place to learn and grow,” explains founder and CEO Bruce Robbins.

Before enjoying KPOP Club Night Xmas Party (Dec. 27) at the House of Blues, hungry holidazers can indulge in soul food at Kitchen + Kocktails next door.

Drink
With Tea Around Town, festive guests can taste fine teas along with sweet and savory treats while being serenaded on a tour of Chicago landmarks (from Millennium Park to the Magnificent Mile) on a pink double-decker bus.

Sip and Paint the View at 360 CHICAGO welcomes aspiring creatives to join Chicago-based artist Coleman Smoll for a guided painting class inspired by the skyline. Tickets include a canvas, paint supplies, an instructor-led class, choice of a beer or glass of wine, and the opportunity to make a unique present.

Speaking of, the venue will be transformed into the city’s highest Holiday Market (Dec. 10) where shoppers can sip and celebrate the season from 1,000 feet above Michigan Avenue while perusing one-of-a-kind artwork and gift items as well as panoramic views of the Chicago skyline and Lake Michigan.

Be Very Merry
Embrace the magic of the season with festive experiences set for the Alma at Hotel Zachary. Throughout November and December, the Wrigleyville venue offers holiday décor and festive music in Alma’s bar and lounge, where spirited cocktails are served. Overnight stays are available at Hotel Zachary, overlooking Gallagher Way’s Winterland (starting Nov. 23).

Whether booked at the hotel or not, weekend holidayers can enjoy Breakfast With Santa (Nov. 29-Dec. 21) which includes photo opps, a letter-writing station, and a buffet of food ($60 for adults/$25 for children).

Rare Tea Cellars’ premium blends and hot chocolate with teddy bear–shaped sandwiches, buttery scones, and fancy desserts are served at the Alma’s Teddy Bear Tea (Dec. 1-28) where each child receives an Alma-branded teddy bear and teddy bear-shaped lollipop ($75 per adult/$50 for children). Hands-on holiday craft sessions led by Kidcreate Studio are also available.

Adults are invited to a Holiday Charcuterie Gift Box Workshop (Dec. 11) with Cheesescapes and Maverick Wines ($70). Apart from Christmas Eve and Christmas Day, Globes on the Terrace ($50+) is offered in December to merrymakers of age. Each Globe offers a unique retreat for two to six guests, complete with blankets, lights, a s’mores station, board games, holiday records, a choice of mulled wine or hot chocolate, and a take-home swag bag.

To partake in these seasonal experiences, visit Alma’s OpenTable. For holiday packages at Hotel Zachary’, visit www.hotelzachary.com/special-offers

Copyright 2025 Rebellious Magazine. All rights reserved. This material may not be published, broadcast, rewritten, or redistributed without written permission.



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