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.

Business Deals & Programs


Mahogany Builders

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!


Kendra scott

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!

The GUild

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.

BabyDolls Boutique

$25 scarves and free gift with $75 purchase

Galleria Liquors

Selling cocktail kits and Journeyman Distillery gift packs at a special price as well as wine specials throughout the store

Lush Cosmetics

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.


Suvarna chiropractic

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.


Butcher’s Tap

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).


The Sill

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%.


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