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!
Ride the 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.
Holly Jolly Trolley Route
2024 Route Coming Soon!
Click these drop-down menus for details on trolley stops, special events, and sales!
2023 Trolley Stops + Nearby Shopping
We’ll have 3 trolleys making 8 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 - Begyle Brewing
1800 W Cuyler Ave - The Wayward Arts Wonderful Wonders Market
1770 W Berteau Ave - Chicago Artisan Market
4325 N Ravenswood Ave - Urban Pooch
4501 N Ravenswood Ave - Magic, Inc.
1838 W Lawrence Ave - Amy’s Candy Bar
4704 N Damen Ave - Redline VR
4702 N Ravenswood Ave
📍 Click here to view the a Google Map of our route with info on nearby shops and restaurants.
Get Your Free Ravenswood Shopping Bag
The first 200 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 – 3:00 PM
2023 Small Business Saturday Sales
- Amy’s Candy Bar
4704 N Damen Ave
Spend $50 (pre-tax) online or in-store and receive a $10 gift certificate to redeem in January.
- Bon Femmes
4917 N Damen Ave
Surprise gift with purchase, while supplies last.
- Hazel
1835 W Montrose Ave
Hazel is giving away $500 in gift cards on Small Business Saturday! Make a purchase at Hazel or Hazel Apparel and enter to win $100, $50, and $20 gift cards. Plus, enjoy free gift wrapping on all purchases in-store.
- The Hive
4706 N Ravenswood Ave
25% off gift cards for dance classes
- Lillstreet Art Center
4401 N Ravenswood Ave
Shop the annual Holiday Art Sale at the Lillstreet Gallery
- Molasses
4919 N Damen Ave
15% off all vintage items
- Ponnopozz
4839 N Damen Ave
BOGO art prints in any size (in-store and online). Cider available while you shop. Spend over $200 and get a coupon for 20% off a future purchase. Orders over $250 receive a free Ponno Baggu plus free gift wrapping.
2023 Small Business Events & Promotions
Trolley Welcome Station @ Hazel
1835 W Montrose Ave
The first 200 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!
Plus, Hilary’s Cookies will be on-site hosting a holiday cookie sale! 11am-3pm, FREE More Info
Chicago Artisan Market @ Artifact Events
4325 N Ravenswood Ave
Twice a year, the Chicago Artisan Market comes to Ravenswood to showcase the best in Chicago and Midwest food, fashion, home goods and art. This curated market celebrates the ingenuity of independent, small businesses who channel their passions into creating one-of-a-kind products. 10am-4pm, $8+ More Info
The Wayward Arts Wonderful Wonders Market
1770 W Berteau Ave, Suite 506
A special one-day pop-up featuring artists and markers from The Wayward Arts community. Escape the frenetic start of holiday season to a loft in the historic Deagan Building to enjoy cider and shop work from incredible local artists. 11am-6pm
Artist Demos & Kids Workshops at Lillstreet Art Center
4401 N Ravenswood Ave
Join Lillstreet for a jam-packed day of free artist demos and kids activities, including tiny pottery wheelthrowing and wire rings! Plus, you can shop handmade gifts at Lillstreet Gallery’s annual Holiday Sale. 11am-5pm More Info
Arsenal Football & Yallpry Market at Redline VR
4401 N Ravenswood Ave
Redline opens at 10am for an Arsenal soccer game. Starting at 11am, they’ll be hosting their Yallpry vendor event. More Info
Pictures With Santa at Urban Pooch
4501 N Ravenswood Ave
Bring your pet to Urban Pooch on Small Business Saturday and take their photo as they visit with Santa Claus! 1-3pm More Info
Milo’s Market Pop-Up @ Begyle Brewing
1800 W Cuyler Ave
Visit the Begyle Brewing taproom on Saturday November 25 and dive into some delicious Mexican-inspired cuisine from Milo’s Market. They’ll be serving a variety of awesome lunch options, including their tasty Birria Grilled Cheese- YUM! 2-5pm More Info
The 2023 Holly Jolly Trolley and Small Business Saturday in Ravenswood are presented by Chicago Artisan Market, Erwin Law, Redline VR, Greater Ravenswood Chamber of Commerce, and Special Service Area #31.
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
Ravenswood Rewards Application: Click here to download
Unwrap Ravenswood Rewards Program Rules
- 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 150 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.
