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  • Holiday Stroll Holiday Stroll

    The Southport Holiday Stroll is a longstanding tradition in West Lakeview where businesses along Southport between Belmont and Irving Park 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!

    All time slots are now reserved for Photos with Santa at Wildwood Photography from 5-7PM. If you didn't get a time slot, look out for Santa roaming through businesses along Southport from 7-9PM! 

    RSVP to the Southport Holiday Stroll & Cocktail Crawl event on Facebook!

  • Cocktail Crawl Cocktail Crawl

    This year, we are expanding the Southport Holiday Stroll to include a ticketed Cocktail Crawl. For the Cocktail Crawl, attendees can sample over 15 different holiday-themed cocktails at participating businesses while they enjoy the festivities of the Southport Holiday Stroll. All businesses participating in the Cocktail Crawl are also part of the Southport Holiday Stroll.

    With a Cocktail Crawl ticket, each cocktail taster will receive a commemorative tasting glass and map guide listing the cocktails and participating business locations, as well as the cocktail samples along the crawl. The Cocktail Crawl check-in location is at Lakeview Chamber office (1409 W. Addison St) from 4:30pm - 7:00pm.

  • Thank You To Our Event Partners! Thank You To Our Event Partners!


  • Business Deals & Programming Business Deals & Programming

    Grassroots: Get 10% off your bill when you mention the Southport Holiday Stroll!
    HuxHemp: Offering non-alcoholic CBD drinks and CBD mint hot chocolate for $5, as well as hot tea for $3. Plus, customers who spend at least $100 will receive a free CBD gift ($8-20 value)! 
    Bentley's Pet Stuff: Buy 2 holiday items, get 10% off, 3 holiday items, get 15% off, 4 holiday items, get 20% off! Plus, they'll have dog nog and mocktails for kids!
    The Red Balloon Co: Receive a surprise discount up to 25% off!
    Click Shoes & More: Spend $100, get $20 off, $200, get $45 off, & $300 get, $75 off!
    FRÍO Gelato: Enjoy a free gelato mini scoop and unlimited samples!
    BabyDolls Boutique: Offering $25 scarves, $20 dainty necklaces, $20 initial necklaces, and buy one get one 50% off on bows!
    Candyality: Enjoy their secret recipe caramel, cheese or combo popcorn at $10 for a large and $4 for a small (retail price $12 and $5, respectively)!
    The Denim Lounge: Receive 20% off on any sale above $100!
    Suvarna Chiropractic: Get 15% off on all packages purchased during the Holiday Stroll!
    CustomEyes: Enjoy 20% off on sunglasses!
    M2 Boutique: Receive a $10 comeback card for every $75 you spend! Plus, enjoy 25% off all handbags!
    Uncle Dan's: Enjoy 15% off regular priced items!
    Stella Blue Design: Buy more, save more! Spend $100 or more, get 15% off, $500 or more, get 20% off, and $3,000 or more, get 30% off!
    StretchLab Lakeview: Receive a 25% discount on all retail items! Plus, they are offering gift cards for a 25-minute stretch for $29 (retail price $49).
    D'Agostino's Pizza: Get a 10% discount on your bill when you mention the Southport Holiday Stroll!
    312 Estates: If you list your home with 312 Estates within the next 6 months, they will provide a professionally shot and directed video of your property for free. See examples at their office during the Southport Holiday Stroll!
    Big City Optical: Get 50% off all sunglasses!
    Mahogany Builders: Offering 10% off labor for any contracts signed before 1/15/19 with a project start date prior to 4/1/19. Call today for your free estimate
    Southport Grocery & Cafe: Receive 15% off their grocery items on the night of the stroll!
    The Music Playhouse of Chicago: Stop by to sing, dance & play instruments to holiday-themed music at their Holiday Open House during the stroll! There will also be crafts and treats!
    Jeni's Splendid Ice Cream: Get an ice cream trio for the price of a standard during the Holiday Stroll!
    Capital One CafeFeaturing complimentary treats and a hot chocolate bar, along with kids activities such as mug and snowflake decorating! Plus, they'll host a drawing to giveaway three $100 Lakeview Gift Cards!
    U.S. Apothecary: Enjoy 20% off all full-price merchandise and 30% off two fragrance collections, as part of their scent of the month sale!
    Indira Salon & Spa: Receive sample bags when you stop in and mention the Southport Holiday Stroll!
    Aligned Modern Health: Purchase $100 in gift cards and receive a $25 bonus card!
    Kendra Scott: Get 15% off your purchase!
    Southport & Irving: Enjoy the Oaxacan old fashion and a special holiday-themed cocktail for $8!
    Foxtrot: Receive 10% off all spirits!
  • Event Details Event Details

    Friday, December 7, 2018
    5:00pm - 9:00pm

    Holiday Stroll

    • FREE (No Ticket Required) 

    Cocktail Crawl


    *The Cocktail Crawl is a rain or shine event.  All ticket-holders must be of legal drinking age.  ID’s will be checked at time of registration.
    **All tastings take place within the businesses listed on the ticketed route.  Cocktail pours are offered in 2 ounce tasting portions at each business.  Over 20 different cocktails will be available to taste along the crawl.  Businesses listed on the crawl are subject to change.


  • Lakeview Gift Card Lakeview Gift Card

    The Lakeview Gift Card will be available for purchase during the event at Sheil Park (3505 N. Southport Ave) from 5-7PM!
    Make the most of your holiday shopping with the Lakeview Gift Card, accepted at more than 80 local shops and restaurants. For a limited time only, get a $20 Bonus Card for every $100 Lakeview Gift Card you buy, with up to $300 in Bonus Cards per household. That’s extra money you can spend on gifts for yourself or others! Buy it in any denomination from $5-$500 per card. Offer expires Dec. 31, 2018.