Welcome to Wonderland with Winter in West Lakeview!

From the Annual Tree Lighting Ceremony to Live Ice Sculpting and more, West Lakeview Special Service Area (SSA) 27 is here this holiday season with enough FREE events and programs spanning from November to January to knock your stockings off!

Winter in West Lakeview Events & Programs

Click on each stamp to learn more!

Sun. Nov 24 – 6:00 - 7:30 PM
St. Alphonsus (1429 W Wellington)
Kick off the Winter with the lighting of the community Tree, featuring carols, free food & bev, a Toy and Kitchenware Drive, and more!

Sun. Nov 24 – 6:00 - 7:30 PM
St. Alphonsus (1429 W Wellington)
Enjoy free family photos with Santa Claus and Disney’s Frozen Characters at the Lakeview Tree Lighting Ceremony!

Tues. Dec 2 - Tues. Dec 16
Submit a valid receipt proving purchase of $25+ at one of 26 Lakeview Business Locations from Dec 2-16 to be entered to win one of three $1000+ gift baskets featuring gift cards, vouchers, and merchandise from participating businesses.

Sat. Dec 7 & Sat. Dec 21 – 12:00 - 3:00 PM
Dec 7: Bitter Pops (3357 N Lincoln) | Dec 21: Sheil Park (3505 N Southport)
In collaboration with Common Pantry, SSA 27 is providing free Gift Wrapping Services to residents of West Lakeview and beyond

Sat. Dec 7, 14, & 21 – 11:00 AM - 2:00 PM
Southport & Paulina CTA Stations
Come out and experience holiday fun with Carolers at Southport & Paulina Station, every Saturday in December leading up to the holidays.

Wed. Dec 25 – 6:00 PM
Southport & Paulina CTA Stations
In collaboration with the Lakeview Chabad, Bring the whole family to gather around the Community Menorah for holiday festivities, treats, and gift bags,

Sat. Jan 25: 2:00 - 4:00 PM & Sun. Jan 26: 12:00 - 2:00 PM
Locations TBA
Watch master ice carvers make winter magic come to life as they sculpt a block of ice into a beautiful creation of the audience’s choosing!