Southport Holiday Stroll & Cocktail Crawl
December 6
5pm-9pm
Enjoy holiday decorations, carolers, photos with Santa, holiday-themed cocktails, treats, special offers & other festivities!
Check-in Locations for Ticket Holders (Check-in is from 4:30-7:30pm day of the event):
Route A: Addison to Irving Park Rd - Check in at Chamber Office, 1409 W. Addison St
Route B: Belmont to Addison - Check in at Sheil Park, 3505 N. Southport Ave
Ticketed Cocktail Crawl
You can choose between two routes for the ticketed Cocktail Crawl and taste 10+ different holiday-themed cocktails on your route while you enjoy the festivities of the Southport Holiday Stroll and shop for gifts at local stores!
The Cocktail Crawl ticket includes a commemorative tasting glass, event guide listing stops along the route, and tastings of the holiday-themed cocktails.
Route A Businesses (Irving Park to Addison)
Mahogany Builders: 3823 N Southport Ave
Steingolds of Chicago: 3737 Southport
Candyality: 3737 N Southport Ave
312 Estates: 3753 N Southport Ave
Music Box Lounge & Garden: 3733 N Southport Ave
Dona Tola: 3751 N Southport Ave
BabyDolls Boutique: 3717 N Southport Ave
Click Shoes & More: 3729 N Southport Ave
Route B Businesses (Addison to Belmont)
Denim Lounge For Men: 3544 N Southport Ave
Galleria Liqueurs-Southport: 3409 N Southport Ave
Kendra Scott: 3426 N Southport Ave
Crosby’s: 3455 N Southport Ave
Tuco & Blondie: 3358 N Southport Ave
Konbini and Kanpai: 1433 W Belmont Unit 1
Arc'teryx: 3441 N Southport Ave
Itoko: 3325 N Southport Ave
Framebridge: 3453 N Southport Ave
Little Goat Diner: 3325 N Southport Ave
Southport Holiday Stroll
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!