Southport Holiday Stroll & Cocktail Crawl

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Southport Holiday Stroll & Cocktail Crawl

Chicago, IL

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Holiday-themed cocktails and festive business specials.

About

Experience the festive spirit of the Southport Holiday Stroll & Cocktail Crawl, a beloved tradition where local businesses extend their hours with special deals and holiday cheer. Attendees can enjoy carolers, capture memorable moments with Santa, and participate in a ticketed cocktail crawl featuring unique holiday-themed drinks.

Our Take

Family Friendly

🎄 🎄 🎄 (3/5)

Best For

Adults seeking festive holiday drinks and shopping

Vibe

Festive, lively, community-oriented

Energy Level

Moderate

Budget

Mid-Range

Photo Friendly

High

Weather Sensitivity

Low

Tags

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.

Location

1409 W. Addison St.
Chicago, IL
60613
Is this your event?

Event Details

Schedule

Businesses stay open late offering special deals and festivities.

Organizer

Lakeview Roscoe Village Chamber of Commerce

Practical Information

Pet Policy

Service animals welcome

Food & Drink

Holiday-themed cocktails available at participating businesses.

Quick Actions

Tips & Advice

  • Purchase your cocktail crawl tickets in advance to guarantee your spot and avoid potential sell-outs.
  • Wear comfortable shoes as you'll be strolling between various businesses to enjoy the festivities and cocktails.
  • Check the event's official website or social media for a list of participating businesses and their specific offerings.
  • Arrive early to maximize your time enjoying the late-night shopping deals and festive atmosphere.
  • Consider using public transportation to navigate the area easily and avoid parking hassles.

Frequently Asked Questions

What is the Southport Holiday Stroll & Cocktail Crawl?

It's a festive event where local businesses stay open late with special deals, featuring carolers, photos with Santa, and a ticketed cocktail crawl.

Are there specific times for the cocktail crawl?

The event schedule notes that businesses stay open late, but specific cocktail crawl times should be confirmed with the organizer.

Is Santa Claus available for photos?

Yes, the event includes opportunities for attendees to take photos with Santa.

What kind of drinks are offered?

Participating businesses offer unique holiday-themed cocktails as part of the ticketed cocktail crawl.

Where can I find a list of participating businesses?

A list of participating businesses and their specific offerings is typically available on the event's official website or social media pages.

Nearby Places (10 total)

Contributors & Updates

The ChristmasLocal.com editorial teamOriginal submitter • Jul 1, 2025