Even though Christmas 2025 is officially in the books, we still have time to enjoy the many, various holiday events in Chicago.  Here are a few unique holiday events that wrap up this weekend and a few that last an additional week.  Join us in keeping the magic of the holiday season going!

Enjoy a newly revised production of Charles Dickens Begrudgingly Performs ‘A Christmas Carol’ Again this final Saturday (3 p.m. or 8 p.m.) or final Sunday (3 p.m.) at Theater Wit (1229 W. Belmont Ave.) in the Lakeview neighborhood.  This show paints an intimate and slightly absurd portrait of the famous author Charles Dickens as he is once again booked to perform his popular Christmas tale just as he has every December since 1853.  However, he might have other ideas.  This production is recommended for ages 15+ and runs 95 minutes with no intermission.  Perhaps you can create a charming new holiday tradition to share with family and friends!

Another of Theater Wit’s holiday hits has returned for its 5^th year with Who’s Holiday! which is also wrapping up this weekend as well.  The tot from The Grinch has grown — Cindy Lou Who, now 40, retells the story of the sordid events after meeting the Grinch from her trailer home in this adults-only romp.  It’s been said that she’s cursing and drinking, super messy, and has had nothing but trouble after five years at the Wit.  In fact, they fear she might make it a double.  Why not come see for yourself if Cindy Lou does indeed make it a double!

Explore Chicago’s vibrant downtown, historic landmarks, cultural institutions and hidden gems all decked out for the holidays on a Big Bus Tours’ Hop-On, Hop-Off Tour through December 31 (10 a.m.-5 p.m.).  Buses arrive every 20-30 minutes at Chicago Riverwalk (98 E. Wacker Dr.) in The Loop and last approximately two hours.  In addition, their local guides have inside knowledge of what you should see and things you should do while on your hop-on, hop-off tour.  It’s a great way to have fun and learn all about Chicago at the same time!

Take in an original play for young audiences at the Cornservatory (4210 N. Lincoln Ave.) in the North Center neighborhood as they present their newest show The Cozy Cabin Tales now through January 4, 2026.  This series of wintry fables and folktales is told by a group of friends waiting out a snowstorm in their cabin with only a small fire to keep them warm as they pass the time by bringing their fantastical tales to life and learning some real-life lessons as well.  These vignettes are a heartwarming way to spend even more time with your family this holiday season!

There’s no better way to celebrate the season than 103 stories above the city at Holidays at Skydeck now through January 4, 2026, at the Skydeck Chicago (233 S. Wacker Dr.) in The Loop.  In addition to the spectacular views from the Skydeck, Willis Tower also sparkles with a dazzling holiday tree, appearances by a strolling Grinch, special surprise live performances from local entertainers, and a holiday market.  Enjoy a festive celebration that’s warm, bright, and indoors!

Since our Bears will be in San Francisco taking on the 49ers this Sunday, here in Chicago the Chicago Bulls will take on the Milwaukee Bucks this Saturday (7 p.m.) and the Chicago Blackhawks will take on the Pittsburgh Penguins this Sunday (6 p.m.) at the United Center (1901 W. Madison St.) in the West Loop!

Sue Moss and Dean’s Team Chicago

“If Bronzeville Winery’s energy could be harvested, this place would have enough backup power to keep its DJ spinning during a blackout.”

Eater.com, 2022

While not actually a winery, there’s no better place in Bronzeville to experience this community.  Founded by Eric Williams of The Silver Room and Cecilia Cuff of The Nascent Group and opened in 2022, Bronzeville Winery blends food, art, and music in the historic Bronzeville neighborhood, and features fresh-grown ingredients from urban gardens, wines from Black-owned wineries and a lively atmosphere with live music and local djs…all with a touch of elegance. 

Start with a French-inspired POACHED PEAR SALAD, which is a spiced poached pear, wild greens, blue cheese, toasted candied pecan, and aged balsamic dressing. Or a BABY GREEN SALAD with mixed Olive Harvey Farm daily market greens and a Green Goddess dressing. ENDIVE SALAD has Belgium endive, citrus, vegan feta cheese, pomegranate seeds in a champagne vinaigrette.

Dinners offer wide-ranging options, with carefully selected wine pairings,  including COCONUT CURRY SALMON, whichpairs Atlantic salmon with red Thai curry, coconut cilantro rice, lemongrass, chili, and lime. They recommend a Portuguese wine, A Laranja Mecânica (‘A Clockwork Orange‘) Fita Preta’ Orange / Arinto, Roupeiro, Derecho, from Alentejo, Portugal. LITTLE CHICKEN + BISCUIT offers a 1/2 fried cornish hen with country gravy, house-baked buttermilk biscuit, good butter,  and Alabama White BBQ Sauce. What kind of wine goes best with chicken and biscuits? I’m curious too! They recommend an Italian Abbazia Di Novacella ‘Kerner’ Trentino, Valle Isarco, Alto Adige, Italy ’22.  TOMATO BASIL FLATBREAD has Heirloom tomato, mozzarella, balsamic reduction, and fresh basil. They suggest a Brown Estate ‘House of Brown’ Red Blend from Napa Valley, California ’21.  MUSHROOM LEEK FLATBREAD has wild mushrooms, caramelized leeks, arugula, and truffle oil, which they suggest pairing with a Spanish  Bodegas Hermanos del Villar, Oro de Castillo Verdejo/ Rueda DO ’20. 

Other selections include SHRIMP + STONEGROUND GRITS, with buttermilk-marinated Gulf Shrimp, served grilled or fried, with creamy stone ground grits, tomato jus, hot honey gastrique, paired with a California -based Brown Estate ‘House of Brown’ Chardonnay from  Napa Valley, California ’21. CREOLE SALMON TAGLIATELLE is a spicy combination of Cajun-spiced salmon, and hand-cut tagliatelle, bathed in a Creole bianco sauce, paired with a festive Italian Cantine Ceci, ‘Licataa’, Vino Spumante Demi-Sec Rosso from Lombardy, Italy.

After dinner, enjoy such frozen treats as VANILLA BEAN ICE CREAM, VEGAN CHOCOLATE GELATO, or a CHEF’S FRUIT SORBET. 

Brunch is served on Sundays only, and includes CHICKEN & BUTTERMILK WAFFLES,  crispy fried chicken thighs with a hot sauce gastrique and golden buttermilk waffles, served with warm maple syrup and butter. SHIRRED BAKED EGG have a rich tomato sauce with herb sauce, and served with a side salad and toasted sourdough bread. ATLANTIC SALMON SALAD  are greens tossed in a preserved lemon vinaigrette, grilled Atlantic salmon, radish, avocado, carrot, tomato and fresh herbs. Others raved about their BREAKFAST BURGER, a quarter pound of Wagyu Beef, with a fried egg, beef bacon, tomato jam, arugula, sharp cheddar cheese on a brioche bun with adobo fries and housemade pickles. 

New Year’s Eve Party!

Ring in 2026 at Bronzeville Winery, which will be transformed to THE EMERALD CITY with live music and more! Step into a world of elegance and celebration as Bronzeville Winery transforms into “The Emerald City” for an unforgettable New Year’s Eve experience!  The evening starts with an elegant four-course meal with two sittings, for $95 per person, which includes a ticket to the THE EMERALD CITY.  Later on, the party includes a complimentary welcome cocktail and champagne toast at midnight, and live music featuring The Michael Damani Band! For information click here.

Bronzeville Winery is located at 4420 S. Cottage Grove Avenue. They are open Wednesday and Thursday from 4pm-9pm, while the kitchen closes at 8:45pm. On Friday and Saturday from 4pm-11pm, with the kitchen closing at 10:45pm. They have a DJ and Live Music from Wednesday – Sunday . Mondays and Tuesdays are for private events only. Sunday Brunch is available from 10am-2pm, with the kitchen closing  at1:30pm. For reservations, click here.

Alison Moran-Powers and Dean’s Team Chicago

The real estate market has always evolved—but the past few years have accelerated change in ways few could have predicted. Shifts in how we work, live, and prioritize our well-being have reshaped what buyers look for in a home. Features that barely registered five years ago are now top of the wish list.

If you’re thinking about selling (or just curious where the market’s heading), here’s a look at what today’s buyers care about most—and why it matters.

1. Dedicated Work-From-Home Space

Five years ago, a spare bedroom was just that—spare. Today, buyers are actively searching for homes that support remote or hybrid work. A dedicated office, flexible bonus room, or even a quiet nook with good lighting can be a major selling point.

Buyers want separation between work and life, and they’re paying attention to layout, noise levels, and internet readiness.

Seller tip: Stage an extra bedroom as a home office to help buyers visualize the potential.

2. Outdoor Living Is No Longer Optional

Backyards, patios, balconies, and outdoor entertaining areas have moved from “nice-to-have” to “must-see.” Buyers value spaces where they can relax, host, or simply get fresh air without leaving home.

Even smaller outdoor areas feel more important now, especially when they’re designed for comfort and usability.

Seller tip: Clean, declutter, and add simple touches like seating or potted plants to highlight outdoor spaces.

3. Move-In Ready Matters More Than Ever

While fixer-uppers once attracted buyers eager for a project, today’s buyers often prefer homes that are ready to go. Rising renovation costs, supply chain delays, and busy schedules have made turnkey properties especially appealing.

Updated kitchens, modern bathrooms, and fresh paint can strongly influence buyer interest.

Seller tip: Small updates—new fixtures, neutral paint, refreshed hardware—can go a long way without a full remodel.

4. Energy Efficiency and Lower Utility Costs

Energy efficiency used to be a bonus feature. Now it’s a priority. Buyers are increasingly aware of monthly costs and environmental impact, and they’re looking for homes with efficient windows, insulation, appliances, and smart thermostats.

Solar panels, once considered niche, are now a real draw in many markets.

Seller tip: Be prepared to highlight energy-saving upgrades and provide average utility costs when possible.

5. Flexible Spaces Over Formal Rooms

Formal dining rooms and rarely used living spaces are losing appeal. Buyers want flexibility—rooms that can adapt to changing needs like fitness areas, guest rooms, playrooms, or creative studios.

Open layouts still matter, but adaptability matters more.

Seller tip: Stage rooms with multi-purpose use in mind to spark ideas.

6. Wellness and Comfort Features

Buyers are thinking beyond square footage. Natural light, good airflow, quiet surroundings, and overall comfort now play a bigger role in decision-making. Homes that “feel good” leave a lasting impression.

This includes everything from lighting and ceiling fans to calming color palettes and thoughtful design.

The Big Takeaway

Today’s buyers are shopping with a lifestyle mindset. They’re asking, How will this home support my daily life—not just now, but years from now?

Understanding these shifts can help sellers position their homes more effectively and help buyers focus on what truly adds value.

If you’re curious how your home stacks up in today’s market—or which updates make the most sense—I’m always happy to help you navigate the next steps.

You know them when you see them…oversized, decked out in bling, fur, tinsel and bedazzled with rhinestones and holiday lights, Ugly Christmas Sweaters have taken on a life of their own.  Consider this observation about Mark Darcy, the character Colin Firth played in “Bridget Jones Diary:”

“His ugly green Christmas sweater,  featuring a massive reindeer complete with fuzzy pompoms and googly eyes, acts as a juxtaposition of his pride and questionable fashion sense.”

Source: UglyChristmasSweater.com

Today, Ugly Christmas Sweaters even have their own national holiday! Since 2011, National Ugly Christmas Sweater Day has grown to be an international event. 

On the third Friday of December, the celebration gives holiday lovers worldwide a chance to wear their ugly Christmas sweaters. In 2025, it’s tomorrow, Friday, December 19.

History of the Ugly Christmas Sweater

The original ugly Christmas sweaters were never intended to be ugly. In fact, they were “really an art in a way,” Asta Skocir, an associate professor at the Fashion Institute of Technology, told ABC7 Chicago news in 2019. 

In fact, according to the blogsite UglyChristmasSweaters.com, its origins date to the 1950s. Early versions were actually joyful, and were called ‘Jingle Bell Sweaters.’ These versions were intended to be classy, decorated with modest designs like reindeer and snowflakes, meant to be festive, and were a natural extension of expressing the Christmas season through fashion.

The garments, according to the website, complemented the refined post-World War Two era look and were deemed helpful when it came to expressing one’s holiday cheer. 

Jingle Bell Sweaters rang out with the advent of the Swinging 60’s, but enjoyed a resurgence in the 1980’s.

Resurgence in the ‘Me Decade’

According to the blogsite Tipsy Elves, the ugly sweater first became a household meme in the 1980s with The Cosby Show’s Dr. Cliff Huxtable, played by Bill Cosby, leading the way. 

Another influence was the insanely popular movie iNational Lampoon’s Christmas Vacation. Chevy Chase’s character added the holiday twist to this look. These well-known leading actors were playing decidedly unhip characters, who had no fashion sense at all. But for some reason, the idea of wearing awful sweaters as an ironic statement, somehow caught on. For a while, ugly holiday sweaters for women and men were easy to find. Then things kind of petered out again in the nineties. 

Here to stay…Ugly Sweater Parties

The city credited with hosting the first modern ugly Christmas sweater party is Vancouver, British Columbia, in 2002, organized by Chris Boyd and Jordan Birch at the Commodore Ballroom as a “cheesy, feel-good, festive party,” sparking a global trend.

The party attracted more than 1,000 guests and benefitted the Make-A-Wish Foundation. 

However, that story was disputed. According to the Michigan-based blog The Perna Team, the story of the ugly sweater party began not in a posh Canadian venue but in a modest student rental on Cedar Street in Kalamazoo. In the winter of 2000, Michael St. Aubin, Jason Weeby, and Bob Wedge, students at Western Michigan University, decided to host a holiday party with a twist. It was an unassuming affair, with fewer than 80 attendees, typical college fare, and a few attendees wearing nostalgic turtlenecks and sweaters.

“We didn’t call them ‘ugly,’” Weeby recalled for the blog. “They represented a sense of nostalgia for us—something warm, quirky, and connected to our childhood memories.”

Chicago’s Ugly Sweater Connection 

According to a 2010  WBBM Radio report by Regine Schlesinger, Clarissa Trujillo of Chicago said that she and her husband were invited to an ugly sweater party three years prior, in 2007. 

“We ran around last minute like crazy, just trying to find the perfect sweater,” she told Schlesinger. “They just weren’t ugly enough.”

So, she got the idea to start her own business, selling ugly holiday sweaters online. She says she can’t necessarily define ugly sweaters, but she knows them when she sees them.

“If I find something that makes me laugh, cringe, anything of the sort, then I know it’s classified as ugly,” she said. 

To this day, Trujillo ‘s website, uglysweaterstore.com, sells the loudest and most garish sweaters she can find.

Chicago: Mecca of Ugly Sweater Parties 

By 2010, Chicago was hosting major ugly sweater parties. 

This weekend, many area bars will be hosting Ugly Christmas Sweater parties, brunches and pub crawls. Click here for more information.

AND….To show off your Chicago pride,  post your best pictures at  #UglyChristmasSweaterDay or #ChristmasSweaterDay

Alison Moran-Powers and Dean’s Team Chicago

Yes, it’s that time again! Time to plan out what we want to achieve in the next year. But, if you really want to be successful and not give up by the end of January, you need a plan. S.M.A.R.T. is an acronym for a plan that has helped many people achieve their goals. Let’s go over the five steps in setting up a smart goals plan.

S stands for specific. You need to clearly define what you want, where and who is involved and why it is important. Just saying you want to get fit is not enough! Saying you will join a gym working out 3 times a week for better cardiovascular health is more specific.

M stands for measurable. This includes a way to track progress, perhaps by numbers or some other way to measure success. For weight loss, it could be a specific number of pounds lost. Instead of just saying I will lose weight, say I will lose 2 pounds per month.

A stands for achievability. Ensure your goal is realistic. Wanting to become a millionaire is great and all, but not necessarily attainable in a year. Budgeting to save $100 a month towards remodeling your kitchen is within reach.

R stands for relevant. Your goals need to align with broader values, objectives, and long-term aspirations. It’s relevant to save for a car to be able to get better employment. Not so relevant to save for a car when your long-term goal is to be debt free.

T stands for timely (or time bound). You need to set specific timeframes and deadlines to complete each task to achieve each goal. This creates focus and urgency. Don’t say get new clients, but say I will sign 4 new clients in the first quarter of the year. 

Smart goals and worksheets along with videos and examples are all over the internet for free. Give it a try, it really works!

Kathleen Weaver-Zech and Dean’s Team Chicago