Chicagoland Winter Events to Kick Off the New Year

Our real estate agents love winter in Chicago. It's a season when neighborhoods and communities all over Chicagoland come alive with festivals and events. These are some of the happenings we're most excited about in the new year!

Upcoming Winter Events in Chicagoland

Winter Whiskey Tasting Festival - Chicago, IL

Address: 1500 N Clybourn Ave, Chicago, IL 60610

Whiskey connoisseurs will want to mark their calendars for January 24, when the Winter Whiskey Tasting Festival returns to Chicago in 2026. Hosted by King's Dining & Entertainment on Chicago's Near North Side, this event offers opportunities to meet expert whiskey brand ambassadors and taste over 20 whiskeys from small-batch and world-class distillers. Be sure to get tickets now, because this festival always sells out!

Chicago Boat Show - Rosemont, IL

Address: 5555 N River Rd, Rosemont, IL 60018

The 2026 Chicago Boat Show will be at the Donald E. Stephens Convention Center in Rosemont from January 28 to February 1. The show provides an incredible opportunity to browse and explore the year's most exciting new boat models and also includes a variety of family-friendly events and attractions, including:

• Food, drinks, and games at the Discover Boating Beach Club
• Bumper Boats for kids ages 2-12
• Indoor stand-up paddleboarding and kayaking in the PaddleFest Pool
• The Huck Finn Trout Pond, a catch-and-release indoor pond where kids 12 and under can fish for free

Ice Skating at McCormick Tribune Ice Rink - Chicago, IL

Address: 1 N Michigan Ave, Chicago, IL 60602

Located in Millennium Park within the Chicago Loop, McCormick Tribune Plaza hosts its annual ice skating throughout the winter months. Reservations are required to skate, but admission is free, and the McCormick Tribune Ice Rink will remain open well into February, weather permitting. 

Downers Grove Ice Festival - Downers Grove, IL

Address: 5001 Main St, Downers Grove, IL 60515

Downers Grove is a charming community in Chicago's southwestern suburbs, and every year the village hosts its annual Downers Grove Ice Festival. Held on January 30-February 1, 2026, this year's festival will include nearly 60 ice sculptures, live carving demonstrations, interactive ice displays, food, drinks, and live entertainment.

Souper Bowl Stroll - Naperville, IL

Address: 55 South Main Street, Suite 351, Naperville, IL, 60540

The first-ever Souper Bowl Stroll will take place on Naperville's Main Street on February 1, hosted by the Downtown Naperville Alliance. Timed to coincide with Chicago Restaurant Week, this event invites guests to sample soups, appetizers, and small bites from some of Naperville's best restaurants on a self-guided stroll.

Winter Sparks: From Bach & Vivaldi - Chicago, IL

Address: 111 S Michigan Ave, Chicago, IL 60603

Held at the Art Institute of Chicago — part of the Grant Park museum complex — Winter Sparks: From Bach & Vivaldi promises to be one of the most enchanting classical music events of the season. Scheduled for February 3 at 7:30 pm, this concert will feature eight talented Apollo's Fire musicians bringing Bach and Vivaldi's works to life. 

Ice Bar at Viceroy - Chicago, IL

Address: 1118 N State St, Chicago, IL 60610

The Ice Bar Experience at the Viceroy Chicago hotel is a beloved winter experience in Chicagoland, and it's returning this year on February 13-16. The hotel's Somerset Patio will transform into an elegant and festive winter wonderland, complete with curated food and drink specials. It's one of the best places to celebrate the season in the upscale Gold Coast neighborhood, whether you're looking for a cozy romantic outing or a toast with friends. 

Winter is a season of fun and excitement in Chicagoland! Contact us today to talk with our real estate agents about finding your dream home in the Chicago area this season.