The Greater Ravenswood Chamber of Commerce runs a holiday program called Unwrap Ravenswood. It pays $75 in local gift cards to shoppers who spend $300 at Ravenswood businesses between Black Friday and Christmas Eve. That works out to 25 cents back on every qualifying dollar. The rules also say the gift cards go to "the first 50 qualifying shoppers who submit a completed form," and each household can submit only once.
Spending $3,000 doesn't earn more than spending $300. The first 50 households whose receipts meet the rules and reach the chamber's mailbox get the cards. So the way to plan your Ravenswood holiday shopping this year has more to do with the rules than with the size of your budget. Small Business Saturday, Nov. 28, happens to be the one day of the season set up to help you clear them quickly.
Fifty households, one envelope
The full rules are on the chamber's Small Business Saturday page. They're stricter than "spend $300."
- The map is fixed. Purchases count only within the program boundaries: Clark Street west to Leavitt Street, one block west of Damen, and Foster Avenue south to Irving Park Road.
- Three businesses minimum. Your $300 has to be spread across at least three qualifying local businesses.
- Each receipt needs $25 before tax and tip. A $14 coffee-and-pastry receipt doesn't count toward the total.
- Groceries and liquor have a ceiling. No more than $100 of your total can come from groceries or liquor.
- Some purchases never count. The chamber lists memberships, medication, legal or accounting services, postage, auto repairs, business-to-business purchases and gasoline as ineligible. Gift receipts aren't accepted.
- It's all by mail. The completed rewards form and copies of your receipts go to the Greater Ravenswood Chamber of Commerce, 1770 W. Berteau Avenue, Suite 101, Chicago, IL 60613. The form asks for your name, return address, phone number, email and ZIP code. Receipts aren't returned, so send copies. Check the submission deadline with the chamber before you mail your form.
- You don't pick the gift cards. The reward is three $25 gift certificates to Ravenswood businesses, randomly selected.
The application is a downloadable PDF linked from the chamber page. You can also pick up a paper copy in person on Small Business Saturday, covered below.
Rules 3 and 6 matter most. The $25 floor means small purchases add nothing, however many you make. A household that finishes its three qualifying stops in late November and mails its envelope that week is ahead of every household still adding up receipts in mid-December. Shopping counts through Christmas Eve, but the gift cards stop after 50 households.
The $25 floor turns Nov. 28 into a three-stop job
The chamber built Small Business Saturday around the same idea, and it brings the stops to you. Three Holly Jolly Trolleys will run a seven-stop loop through the neighborhood from 11 a.m. to 5 p.m. on Saturday, Nov. 28. Rides are free, no tickets are needed, and riders of all ages are welcome.
| Stop | Address | What's there on Nov. 28 |
|---|---|---|
| Hazel | 1835 W. Montrose Ave. | Trolley welcome station, 11 a.m. to 2 p.m.; Hilary's Cookies pop-up |
| Dovetail Brewery | 1800 W. Belle Plaine Ave. | Holiday market in the taproom, noon to 6 p.m. |
| Chicago Artisan Market at Artifact Events | 4325 N. Ravenswood Ave. | Holiday market, 11 a.m. to 5 p.m., admission from $8 |
| Urban Pooch | 4501 N. Ravenswood Ave. | Trolley stop |
| Is/Was Brewing | 5121 N. Ravenswood Ave. | Trolley stop |
| Paper Bunny Press | 4956 N. Damen Ave. | Trolley stop |
| Amy's Candy Bar | 4704 N. Damen Ave. | Trolley stop |
The route covers the area where the rules apply. It starts on Montrose, runs up the Ravenswood Avenue industrial corridor to Is/Was Brewing just south of Foster, then comes back down Damen. All seven stops sit well inside the Clark-to-Leavitt, Foster-to-Irving Park boundary. The chamber's Google map of the route marks nearby shops and restaurants at each stop, which helps when you're looking for a third $25 purchase near the one you just made.
Start at Hazel, because the paperwork is there
The welcome station at Hazel, 1835 W. Montrose, is where the reward program and the trolley meet. From 11 a.m. to 2 p.m., the first 250 shoppers who stop by get a free "Shop Small" tote with offers and items from local businesses, plus a printed Unwrap Ravenswood rewards application.
Hazel hands out 250 totes with applications, and the program pays out to 50 households. If you pick up the form at 11 a.m., you can start saving qualifying receipts before most of the other form holders board a trolley.
Hazel is also running its own promotion that day. Customers who spend $50 or more at Hazel can enter a drawing for a gift basket from Hazel Gifts and Hazel Apparel. Hilary's Cookies will have a holiday pop-up sale at the same station.
Midday runs through the two markets
Two of the seven stops are full holiday markets, and their hours set the pace of the afternoon.
At Artifact Events, 4325 N. Ravenswood, the Chicago Artisan Market returns for Small Business Saturday and Sunday, Nov. 28 and 29, from 11 a.m. to 5 p.m. The chamber describes the newly expanded market as 200-plus local artisans in food, fashion, home and art, with two stocked bars, expanded bistro seating, plated food, and artisan coffee, tea, pastries and desserts. Admission starts at $8. It's the only stop open both days. If you'd rather avoid Saturday's crowds, Sunday is an option, though the free trolley runs only on Saturday.
Dovetail Brewery, 1800 W. Belle Plaine, hosts its holiday market in the taproom from noon to 6 p.m., with handcrafted, locally made goods. It closes an hour after the last trolley, so Dovetail can be your final stop if you finish the loop with a qualifying receipt still to go.
Krampus sets the afternoon schedule
The chamber's Small Business Saturday lineup includes a guest from Alpine folklore. Chicago Krampus, the dark counterpart to Saint Nicholas, will pose for free photos at Dovetail Brewery from noon to 2 p.m., then at Is/Was Brewing, 5121 N. Ravenswood, from 3 to 5 p.m.
The two appearances sit at opposite ends of the route. That gives families a simple plan for the day:
- 11 a.m. Hazel for the tote, the application and the Hilary's Cookies pop-up
- Noon to 2 p.m. Dovetail's holiday market and the first Krampus photo window
- Early afternoon Chicago Artisan Market at Artifact Events, or Urban Pooch next door on Ravenswood
- 3 to 5 p.m. Is/Was Brewing for the second Krampus window
- Back south on Damen Paper Bunny Press and Amy's Candy Bar before the trolleys stop at 5
The chamber lists one online deal so far. DEFY Bags is taking 20% off its web store from Black Friday through Cyber Monday with the code BLACK20.
Dec. 5 brings the season to Wilson Avenue
One week after the trolley, the Ravenswood Neighbors Association holds its 7th annual Ravenswood Light Up Nights Festival and Holiday Market. It runs Saturday, Dec. 5, from 3 to 7 p.m. on Wilson Avenue between Ravenswood and Hermitage. The event is free.
| Time | What's happening |
|---|---|
| 3 p.m. | Event opens; holiday market and all activities begin |
| 3 to 5 p.m. | Live ice sculpting by Johnson Studios Ice Sculptures, outdoors |
| 3 to 5 p.m. | Photos with Santa inside the holiday market; bring your own camera |
| 5 to 5:30 p.m. | Brass band performs outdoors |
| 5:30 p.m. | Tree lighting at Wilson and Hermitage with the Chicago Chorus Girl Project, followed by community caroling |
| 7 p.m. | Holiday market closes and the event ends |
The festival also has a kids' scavenger hunt, photo stations, food and drink vendors, and free hot cocoa while supplies last. The indoor holiday market's 2026 vendors are Alexandra Jamroz Designs, Blue Casa Studios by Jaqui, DFG Designs & The Alchemy Kitchen, Fruit Cellar, Grunewald Arts, Hilary's Cookies, The Hive Supply Company, Lincoln Ice Cream Company, Mangel Florist + Surroundings by Colin, Mitzibell, Monarch Beauty Farm, Ravenswood Handmade, and Ruckus Teens at Concordia Place.
Proceeds from the festival's raffle go to the RNA and the Ravenswood Community Services Food Pantry. The raffle prizes are gift baskets donated by local Chicago businesses and are displayed inside the holiday market. The RNA credits All Saints Episcopal Church and the Greater Ravenswood Chamber of Commerce as partners. Wilson between Ravenswood and Hermitage is well inside the Unwrap Ravenswood map, and Dec. 5 falls within its Black Friday to Christmas Eve window.
Who pays for the free trolley
The trolley, the welcome station and the Krampus photos are free to riders because a group of sponsors covers the cost. The 2026 Holly Jolly Trolley and Small Business Saturday are presented by Chicago Artisan Market, Erwin Law, Dovetail Brewery, Hazel, Urban Pooch, Wintrust Bank, JB Cleaners, Bad Luck Club, the Greater Ravenswood Chamber of Commerce and Special Service Area #31. Four of those sponsors are also trolley stops, and the Unwrap Ravenswood gift cards are good only at Ravenswood businesses. Every part of the program is designed to keep holiday spending within the boundary map.
Five days after Light Up Nights, on Thursday, Dec. 10, the chamber holds the Ravenswood x Andersonville Holiday Mixer from 6 to 8 p.m. at Chicago Magic Lounge, 5050 N. Clark St.
At Juliana & Ben Yeager, we spend Small Business Saturday on the same Ravenswood streets as our neighbors, and we're glad to share where we find good gifts near each trolley stop. If you're comparing Ravenswood blocks for a move in the new year, or wondering what your home is worth before spring, we can walk the route with you and talk it through. Reach out any time to Find My Home.
