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When and Where
- November 28, 2026
- 11am – 5pm (additional hours at all participating venues)
- Ravenswood Small Businesses
Details
- Find the best sales, promotions and events taking place around Ravenswood
- The Holly Jolly Trolley is free and will allow you to easily travel and discover exciting local shopping offers
- Unwrap Ravenswood: Spend $300 between at least 3 Ravenswood businesses from Black Friday through Christmas Eve to earn $75 in gift-cards to local shops and restaurants.
Sponsorship Opportunities
Packed with unique shops, delicious food, skilled artists and friendly people, Ravenswood is a delightful place to explore this season for those seeking thoughtful, out-of-the-ordinary gifts. The Greater Ravenswood Chamber of Commerce (GRCC) is encouraging everyone to shop small over the holidays by making it simple, fun and rewarding to support our favorite local businesses. We’re looking forward to another magical Small Business Saturday in Ravenswood!
Holly Jolly Trolley
We’re excited to bring back one of Ravenswood’s favorite holiday traditions— the Small Business Saturday Holly Jolly Trolley!
Our trolleys will make multiple stops around the neighborhood, connecting you to hundreds of incredible small businesses without any stress about parking! No tickets are necessary and riders of all ages are welcome aboard.
2025 Holly Jolly Trolley Route
Click these drop-down menus for details on trolley stops, special events, and sales!
We’ll have 3 trolleys making 7 stops around the neighborhood. The Holly Jolly Trolley is free to ride from 11 AM to 5 PM.
- Hazel – Trolley Welcome Station
1835 W Montrose Ave - Dovetail Brewery
1800 W Belle Plaine Ave - Chicago Artisan Market
4325 N Ravenswood Ave - Urban Pooch
4501 N Ravenswood Ave - Is/Was Brewing
5121 N Ravenswood Ave - Paper Bunny Press
4956 N Damen Ave - Amy’s Candy Bar
4704 N Damen Ave
📍 Click here to view the Google Map of our route with info on nearby shops and restaurants.
The first 250 shoppers to stop by the GRCC’s Small Biz Sat Welcome Station will receive a FREE “Shop Small” tote bag with offers and items from local businesses- plus an Unwrap Ravenswood rewards application. Spend $300 at at least 3 neighborhood small businesses to earn $75 in gift cards to local shops and restaurants!
We’ll also be joined by Hilary’s Cookies for a holiday pop-up sale!
Location: Hazel (1835 W Montrose Ave)
Hours: 11:00 – 2:00 PM
Coming soon!
Trolley Welcome Station @ Hazel
1835 W Montrose Ave
The first 250 shoppers to stop by our Small Biz Sat Welcome Station will receive a Ravenswood tote bag with offers and items from local businesses and an Unwrap Ravenswood rewards application. Spend $300 at at least 3 neighborhood small businesses to earn $75 in gift cards to local shops and restaurants! 11am-2pm (while supplies last!)
Chicago Artisan Market @ Artifact Events
4325 N Ravenswood Ave
The Chicago Artisan Market returns to Artifact Events on Small Business Saturday & Sunday. The newly expanded market will feature 200+ talented local artisans in food, fashion, home & art- along with two stocked bars, expanded bistro seating, plated food, and artisan coffee, tea, pastries & desserts. 11am-5pm, $8+ More Info
Dovetail Holiday Market
1800 W Belle Plaine Ave
Visit the Dovetail Brewery taproom on Saturday November 28th for unique, thoughtful, and locally-made handcrafted items, kind of like their beer! 12-6pm More Info
More coming soon!
Unwrap Ravenswood Rewards Program
Our annual winter rewards program invites shoppers to Unwrap Ravenswood! From Black Friday through Christmas Eve, shoppers that spend $300 between a minimum of 3 qualifying local businesses will receive $75 in gift cards to local stores and restaurants.
Boundaries: Clark St west to Leavitt St (1 block west of Damen Ave), and Foster Ave south to Irving Park Rd
- Download the Application (PDF)- Click here to download
- Holiday Shoppers that spend a total of $300 within the above boundaries on retail products, dining, gift certificates, or services will be eligible to receive a rebate of $75 in the form of 3 $25 gift cards to Ravenswood businesses.
- Shoppers must complete and send in a Holiday Shopper Rewards Form (found above) with qualifying receipts from a minimum of 3 businesses.
- A minimum of $25, before tax and gratuity, must be spent at a qualifying business for a receipt to be included in the total. A maximum of $100 can be utilized for groceries and/or liquor. Medications or memberships are not allowed to be included in total.
- Ineligible purchases include but are not limited to memberships, medication, legal or accounting services, postage, automobile repairs, business-to-business purchases and gasoline.
- Completed Rewards Forms and copies of receipts must be mailed to the Greater Ravenswood Chamber of Commerce office (1770 W. Berteau Avenue, Suite 101 Chicago IL 60613).
- All copies of receipts should be submitted with a completed Shopper Rewards Form, including name, return address, phone number, email address and zip code.
- Rewards in the form of 3 $25 gift certificates to Ravenswood business will be distributed to the first 50 qualifying shoppers who submit a completed form. Limit one submission per household. Gift cards will be randomly selected.
- Copies of receipts and a completed form must be submitted by Monday, January 6, 2025.
- No gift receipts allowed. Receipts will not be returned.
2026 Sponsors
The 2026 Holly Jolly Trolley and Small Business Saturday in Ravenswood are presented by Chicago Artisan Market, Erwin Law, Dovetail Brewery, Hazel, Urban Pooch, Wintrust Bank, JB Cleaners, Bad Luck Club, Greater Ravenswood Chamber of Commerce, and Special Service Area #31.
Connecting business and community.
Become a GRCC Member
The Greater Ravenswood Chamber of Commerce is committed to building a Ravenswood that connects business and community, one member at a time.
Check out the benefits of membership here.