Southport Holiday Stroll & Cocktail Crawl
Enjoy holiday decorations, carolers, photos with Santa, holiday-themed cocktails, treats, special offers & other festivities!
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!
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)
Business Deals & Programs
Offering discounts on Design Services and Remodeling Projects. Raffle for one complimentary room design.
The Denim Lounge For Men
10% off any sale $100 or more.
Alice & Wonder
15% off your purchase, including an additional 15% off of sale!
Receive a free small size of any flavor of their specialty gourmet popcorn with any purchase of $20 or more
Discover CBD Lakeview
15% off of total purchases of $150 or more.
Southport Grocery & Cafe
15% off all groceries! Plus, they are hosting a Secret Supper during the event.
$25 scarves and free gift with $75 purchase
Selling cocktail kits and Journeyman Distillery gift packs at a special price as well as wine specials throughout the store
Free samples of their Holiday shower gels
Port & Park Bistro & Bar
Free dessert with any full entre ordered (not valid with any other offer)
Elite Chicago Spa
20% Any Service Gift Card - Good for 6 months from date of event.
20% off all packages purchased on 12/3 - 12/10. They will also have a raffle for your chance to win 6 adjustments and massages.
25% off of a lifetime membership during the holiday stroll. They will be stationed at Suvarna Chiropractic, so stop in to enter their raffle for your chance to win one month free trial membership.
Stop in for $8 Irish Car Bombs.
The Green Lady Tavern
$5 off a bottle of 18th Street Distillery bourbon for the month of December (while supplies last).
15% off $50+ through the month of December
Aura Candle Bar
Buy 3, Get 1 Free Pre-Poured Candles
Click Shoes & More
Spend $75, get 15% off. Spend $125, get 20% off. Spend $175, get 25%.