• Cocktail Crawl tickets are now SOLD OUT. You can still come by to enjoy the great deals and festivities of the Southport Holiday Stroll!

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  • Event Details Event Details

    Friday, December 6, 2019
    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 15 different cocktails will be available to taste along the crawl.  Businesses listed on the crawl are subject to change.


  • 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!


    Photos with Santa:
    All time slots have been reserved for Photos with Santa taking place at Sheil Park from 5-7pm. If you didn't get a time slot, look out for Santa roaming through businesses along Southport from 7-9PM during the Southport Holiday Stroll & Cocktail Crawl! 

    Thank you to our Photos with Santa sponsor, Audrey Hoover Photography!

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

  • Cocktail Crawl Cocktail Crawl

    For the Cocktail Crawl, attendees can taste 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 participating businesses and various cocktails. The Cocktail Crawl Check-In location is at Sheil Park (3505 N. Southport Ave) from 4:30 - 7:30pm.

    This year, we are hiding 10 Lakeview Gift Card vouchers in the Cocktail Crawl event bags with amounts from $10 to $100! Will you be one of the lucky ones to find the green ticket? Find out this Friday and get excited to enjoy delicious cocktails while  you do your holiday shopping!

  • Sign Your Kids Up For An Art Class While You Shop! Sign Your Kids Up For An Art Class While You Shop!

    Sign your kids up for a night of art fun at KidCreate Art Studio while you get your holiday shopping done at the Southport Holiday Stroll & Cocktail Crawl! The kids will work on their holiday gift list too, as they will be making beautiful holiday-themed clay mosaics. Who wouldn't want to receive that gift? Learn more and sign your kids up here!
  • Thank You To Our Event Partners! Thank You To Our Event Partners!




  • Business Deals & Activities Business Deals & Activities

    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.
    BabyDolls Boutique: Buy one fashion jewelry piece, get the second for 30% off! Plus, select $20 scarves will be available. 
    Big City Optical: Enjoy discounts on prescription eyewear and sunglasses! Plus, they will have a craft station to create custom holographic eyeglasses to view the holiday lights and their furry elf, Miss Stevie the Wonder Dog Optician will be there!
    Candyality: Treat Yo'self with a free regular sized bag of house-made caramel, cheese or combo popcorn with any purchase of $25 or more!
    Capital One Cafe: will have a free hot chocolate bar and create your own mug station! *Close at 8pm.
    Couture Nails & Waxing: Enjoy 20% off any service!
    CustomEyes: Enjoy 20% off your purchase!
    Click Shoes & More: Save 15% on purchase of $75, 20% on purchase of $125 and 25% on purchase of $175!
    The Denim Lounge: Receive 20% off any sale $75 or more!
    FRÍO Gelato: Enjoy a free 2 oz hot choco-lato and free gelato samples!
    Kendra Scott: Donating 20% of their proceeds from that night to Friends of Lakeview! *Close at 8pm.
    KidCreate Art Studio: Offering a drop off art class for kids from 5:30-8:30pm. Register here.
    M2 Boutique: Secret sales all night long!
    Mahogany Builders: Handing out coupons for 5% off home improvement and handyman projects. (See coupon for redemption period and offer details)
    Mothership Launchpad: Enjoy mocktails and cookie decorating!
    Music Box Theatre Lounge: Get $2 off any glass of Music Box or Dablon wine (including their Mulled Wine) or $4 off any bottle of Music Box or Dablon wine to take home with you or give as a wonderful holiday gift!
    The Music Playhouse of Chicago: Stop by for festive singing, dancing, crafts and treats from 4-7pm for their free Holiday Open House!
    Paper Source: Crafting activities for kids and adults!
    Port & Park Bistro & Bar: Enjoy 50% off appetizers and 40% off the entire food menu!
    The Red Balloon Co: Receive discounts on select merchandise!
    Stella Blue Design: Buy more, save more! Spend $3,000 or more get 30% off, $1,000 or more get 25% off, $500 or more get 20% off, $100 or more get 15% off. Plus, all red-lined items will be an additional 10% off for ONE NIGHT ONLY!
    StretchLab Lakeview: Offering a special deal of $19 for 25 minute stretches (retail $49), and will have a free stretch to Christmas music from 6-7pm!
    Suvarna Chiropractic: Offering 20% off all packages! Plus, they will have photos with Frosty and a choir outside serving hot chocolate!

    Tied House: Enjoy happy hour food and drink specials that will be running all night long! Plus they will have samples of their delicious dessert Bouchons that you can taste!
  • 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 4:30-7:30PM!
    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, 2019. Bonus cards can be used between January 1st and March 31st, 2020, creating the perfect opportunity to indulge in post-holiday shopping!