Shop Local: Chicago and North Shore Shopping Guide for Black Friday, Small Business Saturday and Cyber Monday

‘Tis the holiday shopping season! Sure, it can be easy to hop on Amazon to do your holiday shopping, but we encourage you to remember to support your local shops whenever possible, especially during the holidays when competition is so high. We’ve made it easy for you with our list of Chicago small businesses to support both in person and online this weekend.

Andreas Hogue Gifts

840 Willow Rd, Suite K, Northbrook & 901 N. Milwaukee Ave, Unit 650, Vernon Hills

Special Promotion: Free Gift with in-store purchase; save 20% off all shampoo, conditioner and styling products with code: LOVELOCAL when you shop online November 25-28. They will also host a Warmth Drive to benefit Youth Services of Glenview/Northbrook, and are collecting new hats, mittens, blankets, socks… anything warm and cozy!

Downtown Highland Park

440 Central Avenue, Highland Park

Special Promotion: Downtown Highland Park Alliance is proud to host their annual Sugar Plum Shopping Spree on Saturday, November 27th from 10am – 5pm, in conjunction with Small Business Saturday. Shoppers are invited to get their holiday shopping done while enjoying seasonal special deals, holiday treats, and incentives, including the opportunity to win a $250 gift card at their Downtown Highland Park business of choice. And, Port Clinton Square will host live seasonal music and Santa, while carolers roam the streets from 2-4 pm making this a day downtown to remember!

Cowboys and Astronauts

1478 W Summerdale Ave., Chicago

Special Promotion: Watch their Instagram for the announcement!

Timeless Toys, LTD.

4749 N Lincoln Ave, Chicago

Small Business Saturday: Buy $100 in gift cards and get a $25 gift card free! Spend over $100 and receive a free scratch off ticket worth up to 50% off (in store or online) and receive a $10 gift card to another local business (until supplies last).

Cyber Monday: Use promo code “cyber21” to receive a 10% discount at checkout.

Alice & Wonder

956 W Webster Ave, & 3542 N Southport Ave., Chicago

Special Promotion: 20% off through Cyber Monday online and in stores, in addition to the daily promotions below:

11/26: 30% off glassware

11/27: 30% off Chicago Apparel

11/28: 30% off Mad Hatter

11/29: 30% of socks

Jayson Home

1885 N Clybourn Ave., Chicago

Thanksgiving Day & Black Friday: 20% off all furniture and free shipping on all orders over $75.

Sunday, Nov. 28 & Cyber Monday: 20% off everything site-wide and free shipping on every order.

Rogers Park

Photographed by Matthew | © 2019 TK Photography

Live Love Shop Rogers Park: offering rebates to shoppers who patronize independently owned businesses in Rogers Park during the holiday season; $50 for $150 spent and $75 for $200. Check out Walk Chalk Howard Street featuring 3D art by Nate Baranowski displayed at local Rogers Park businesses.


The Greater Ravenswood Chamber of Commerce is encouraging everyone to shop small over the holidays by making it fun and rewarding to support our favorite local businesses. Four trolleys will make their way through the neighborhood from 11am – 5pm with stops located along Damen, Montrose, Wilson, Irving Park, and Ravenswood Avenue. The trolley is free and riders of all ages are welcome.

Weekend Promotions and Events:

DEFY Bags is hosting a store-wide sale from Friday, Nov. 26th to Monday, Nov. 29th. Get 25% off purchases using special codes BLACK25 on Black Friday, SMALL25 on Small Business Saturday, or CYBER25 on Cyber Monday at check out.

Gnome Brew is offering discounts on equipment and recipe kit combos from Friday to Monday! Kits make great gifting ideas for the home brewer. Choose from beginner to advanced kits including a Wine Equipment Kit.

KOVAL is offering a 10% discount on all items in the KOVAL store only on Small Business Saturday! Stock up on holiday gifts like special release whiskeys (including the brand-new release of KOVAL Rye aged in Maple Syrup casks), winter merchandise, and more!

Lillistreet Gallery’s week-long Holiday Sale starts on Small Business Saturday, and carries until Friday, December 9th! Each day, a new item category of artist-made goods like mugs, earrings, and textiles, will go on sale in store and online.

Bon Femmes is offering 10% off for Black Friday and Small Business Saturday.

Ravensgoods 20% off all in-store purchases on Small Business Saturday.

Want more? Support local and check out our Best of 2021: Shopping winners!

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Macaire Douglas lives in the Chicago suburbs with her husband and two sons. She proudly supports Save Abandoned Babies Foundation, a Chicago-based nonprofit organization that works tirelessly to prevent the illegal abandonment of newborns nationwide. Since its inception in 2000, more than 3,600 newborns have been safely surrendered and adopted into loving homes.