Winter has arrived in Chicago! As flurries of snow settle in over our city, the streets come alive with holiday greenery, bows, and colorful lights. Now is the best time to get out and explore all that Chicago has to offer this winter season, and Jameson Sotheby’s International Realty is proud to showcase some of our favorites: from local gift shopping, to holiday-themed events, to warm winter treats. Check out our guide below for the best ways to make your Chicago winter special.

Places to Go, Things to Do

The Art Institute Of Chicago

Season Starts September 12th

Christkindle Market

November 19th - December 24th

27th Annual Lincoln Park Zoolights: New Features & Animal Habitats

Kicks Off November 19th

Ice Skating At Gallagher Way, Wrigley Field

Starts November 20th

Serenity: Winter Flower Show
At Garfield Park Conservatory

November 24th - January 9th

Immersive Van Gogh

Exhibited Through February 6th

Polar Express At Chicago Union Station

Starts December 1st

A Christmas Carol At Goodman Theatre

November 20th - December 31st

Light Up The Lake At Navy Pier

Through January 2nd

Ice Skating At Maggie Daley

Season Starts November 19th

Illumination At Morton Arboretum

Starts November 20th

The Nutcracker At Art On The Mart

November 26th - December 30th

Cocktails And Curling At Kaiser Tiger

All Winter Season

Trans-siberian Orchestra:
Christmas Eve & Other Stories

December 23rd

Renegade Craft Fair Chicago

December 18 - 19th

Chicago Polar Plunge

March 6th

Mug-nificient | The Best Places to Sip Hot Chocolate

Katherine Anne Confections

Logan Square

Mindy’s

Wicker Park

Uncommon Ground

Lake View | Edgewater

Ghirardelli Chocolate Co.

River North

Julius Meinl Café

Lincoln Square | Lake View

Firecakes Donuts

River North | Lincoln Park
Oak Park | Naperville

Little Branch Café

South Loop

Eataly

River North

Chocolat Uzma

Pilsen

Xoco

River North

Shop Small and Local

Nothing beats the excitement of going window shopping in your local neighborhood to peek at the latest holiday offerings from your favorite local shops. This season, we encourage you to shop small and take advantage of Chicago’s unique retail, spa, and restaurant offerings:

Apparel & Accessories

Panerai Boutique

Gold Coast

Laudi Vini

Lincoln Park

K. Stonehill Creations

Old Town

Indochino

Gold Coast

Penelope’s

East Village

Marine Layer

Wicker Park

Health & Beauty

Aesop

West Loop

Bluemercury

River North

Mojo Spa

Wicker Park

Merz Apothecary

Lincoln Square

Allyu Spa

Gold Coast

Essa Dora Salon & Spa

Old Town

Home & Floral

Christine Noelle Design

Gold Coast

Something More Goods

Old Town

Art Effect

Lincoln Park

GL Home Decor

Andersonville

Eskell

Bucktown

Neighborly

Lincoln Square

Food & Wine

Sugar Bliss

Loop

Terry’s Toffee

Lincoln Park

Joe’s Wine Cellar

Wicker Park

Veruca Chocolates

Near North Side

Galleria Liquers

Lake View

Publican Quality Meats

West Loop

Watch This Holiday Season

The BMO Harris Bank Lights Festival celebrates its 30th year in 2021 as one of Chicago’s most spectacular parades, featuring more than 1 million lights along the Magnificent Mile that are accompanied by floats, baloons, and more, before culminating in a fireworks show.

Be sure to catch the broadcast of this spectacular event on ABC 7 Chicago at 6 p.m. on Saturday, December 11 and again on Saturday, December 25 at 12 p.m. Helping to make this event possible are Gail Spreen and Noreen Chip, two of our Jameson Sotheby’s International Realty Agents.

Eat This Holiday Season

Our featured Chicago eatery of the season is Sugar Bliss Patisserie, located at the base of the Palmer House Hilton. Boasting fantastic cupcakes, macarons, and many other baked goods, this patisserie has been a sweets staple in the Downtown Loop area since 2009.

Sugar Bliss is a Certified WBENC Women in Business Enterprise and a National Minority Supplier. It is owned by Teresa Ging, a graduate of the University of Chicago whose work has earned her numerous awards including 2019’s Enterprising Women of the Year.

Check back to Extraordinary Living all month for more holiday content!