Holidays in Lakeview & Roscoe Village

Events

Southport Holiday Stroll & Cocktail Crawl

Friday, December 3 from 5-9PM at businesses along Southport Ave from Belmont to Irving Park Rd.

The Southport Holiday Stroll is a longstanding tradition in West Lakeview where break out the holly and stay open late offering special holiday deals and festivities. The Southport Holiday Stroll is free to attend and includes special deals from local businesses, carol singers, photos with Santa, holiday treats, and other surprises!

The ticketed Cocktail Crawl features two routes and attendees can sample 10 different holiday-themed cocktails on either Route A or Route B while they enjoy the festivities of the Southport Holiday Stroll.

WinterFest

Sat, 12/4 & Sun, 12/5 in Roscoe Village

In partnership with RVN, Winterfest will kick off on Sat, 12/4 with a tree lighting ceremony at 5pm and then local shops will stay open late until 9pm for your holiday shopping with festive treats and special offerings! On Sun, 12/5, the holiday festivities will continue from 1-5pm with carolers, Santa, sleigh rides, and family-friendly activities at local businesses.

Plus, check out the businesses participating in our Window Decorating Contest to vote for your favorite storefront!

Lakeview Tree Lighting Ceremony

Sunday, Nov. 21 at 6pm at St. Alphonsus Church

Come celebrate the kickoff of the holiday season in Lakeview with the lighting of Lakeview's community Christmas tree! Enjoy live performances and a special visit from Santa. The festivities will take place directly outside St. Alphonsus on the corner of Lincoln/Wellington/Southport.