Southport Holiday Stroll & Cocktail Crawl
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Southport Holiday Stroll & Cocktail Crawl

Holiday cocktail crawl with festive business offerings.

About

Experience the festive Southport Holiday Stroll & Cocktail Crawl, a cherished tradition where local businesses deck their halls and stay open late. Enjoy holiday-themed cocktails during the ticketed crawl, browse special deals, and soak in the cheerful atmosphere with carolers and opportunities for photos with Santa.

Our Take

Family Friendly

๐ŸŽ„ ๐ŸŽ„ ๐ŸŽ„ ๐ŸŽ„ โšช (4/5)

Best For

Adults and families

Vibe

Festive, community-oriented, lively

Energy Level

Moderate

Budget

$$

Photo Friendly

๐Ÿ“ท ๐Ÿ“ท ๐Ÿ“ท ๐Ÿ“ท ๐Ÿ“ท (4/5)

Weather Sensitivity

Moderate

Special Events & Promotions

  • Businesses offer special deals and festivities.
  • Ticketed Cocktail Crawl with holiday-themed cocktails.
  • Photos with Santa available.

Tags

food drink partiesholiday marketcommunity celebrationseasonal activitiesholiday traditionSanta visitsfestive foodholiday shopping

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

Event Details

Pricing

$$

Duration

1 hour

Ages

All ages

Neighborhood

Lakeview Roscoe Village

Timed Entry

Yes

Organizer

Lakeview Roscoe Village Chamber of Commerce

Practical Information

Pet Policy

No pets allowed

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 participating businesses along Southport.
  • Arrive early to maximize your enjoyment of the holiday deals and festivities before the Cocktail Crawl officially begins.
  • Check the list of participating businesses beforehand to plan your route and ensure you visit your favorite spots.
  • Bring a non-perishable food item to donate if any businesses are collecting for local charities, as is common during holiday events.

Frequently Asked Questions

What is the Southport Holiday Stroll & Cocktail Crawl?

It's a festive event where businesses on Southport stay open late with special deals, decorations, and entertainment like carolers and Santa, featuring a ticketed cocktail crawl.

How do I participate in the Cocktail Crawl?

You will need to purchase tickets for the Cocktail Crawl, which will grant you access to enjoy holiday-themed cocktails at participating businesses.

Are there activities for all ages?

Yes, the stroll itself is family-friendly with carolers and Santa photos. The Cocktail Crawl portion is for those 21 and older.

What kind of deals can I expect from businesses?

Participating businesses often offer special discounts on merchandise, services, or seasonal items during the event.

Where is the event located?

The event takes place along the Southport corridor in Chicago, with the Chamber of Commerce located at 1409 W. Addison St.

Nearby Places (10 total)

Contributors & Updates

Last Updated: Oct 23, 2025
Original Submitter: Sep 17, 2025 The ChristmasLocal.com editorial team

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