"Our trolleys will make multiple stops around the neighborhood, connecting you to hundreds of incredible small businesses without any stress about parking!" That's the promise on the Greater Ravenswood Chamber of Commerce's Small Business Saturday page, and it holds up. The rest of that page lays out a day built around timing. The giveaways are limited. The best of them go out only in the first three hours. The rewards program pays only if your receipts come from at least three different businesses. So Saturday, November 28, works best if you already know your route before the first trolley leaves.
That's a little over three weeks away. Below is how the day and the month after it fit together.
The First Three Hours Are the Scarce Ones
The Holly Jolly Trolley is free and runs from 11 a.m. to 5 p.m. You don't need a ticket, and riders of all ages are welcome. The chamber plans to run three trolleys over seven stops.
The trolley runs until 5, but the welcome station doesn't. It's at Hazel, 1835 W Montrose Ave, and it's open only from 11 a.m. to 2 p.m. The first 250 shoppers get a free "Shop Small" tote with offers and items from local businesses. The tote also holds the application for Unwrap Ravenswood, the chamber's holiday rewards program. Hilary's Cookies will be at Hazel for a holiday pop-up during the same hours.
The tote goes to the first 250 people, the station closes three hours before the trolleys stop, and the tote carries the form that turns the rest of your holiday shopping into gift cards. Someone who starts at 3 p.m. still gets the trolley and the shops. They miss the bag and have to find the form some other way. The chamber also posts the Unwrap Ravenswood application online, so a late start won't lock you out. It just takes a step that early arrivals skip.
Seven Stops on Two Spines
Most stops sit on two north-south streets, Ravenswood Avenue along the Metra embankment and Damen Avenue to the west. Montrose and Belle Plaine connect them. Here's the 2026 lineup as the chamber lists it:
| Stop | Address | What's there on Nov. 28 |
|---|---|---|
| Hazel | 1835 W Montrose Ave | Welcome station, totes and Hilary's Cookies pop-up, 11 a.m. to 2 p.m. |
| Dovetail Brewery | 1800 W Belle Plaine Ave | Holiday market in the taproom, noon to 6 p.m. |
| Chicago Artisan Market | 4325 N Ravenswood Ave | 200+ artisans at Artifact Events, 11 a.m. to 5 p.m. |
| 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 chamber hasn't finished the list. Its 2026 sales section still says "Coming soon!" and the events list ends with "More coming soon!" More deals will likely be posted before the 28th, so check back the week of Thanksgiving. The chamber also links a Google map of the route marking nearby shops and restaurants. Pull it up before you head out.
Four of the seven stops are on the event's sponsor list: Chicago Artisan Market, Dovetail Brewery, Hazel and Urban Pooch. The other presenters are Erwin Law, Wintrust Bank, JB Cleaners, Bad Luck Club, the chamber itself and Special Service Area #31. Together, those sponsors and the chamber are what keep the trolley free to ride.
The One Stop With a Ticket
Everything on the trolley route is free to walk into except the Chicago Artisan Market at Artifact Events. It's also the only part of the day that runs two days. The market is open Saturday and Sunday, November 28 and 29, 11 a.m. to 5 p.m. both days, with more than 200 artisans across two buildings. The chamber says this year's expanded market will cover food, fashion, home and art, with two stocked bars, more bistro seating, plated food, and artisan coffee, tea, pastries and desserts.
Advance prices on the market's ticket page:
- General admission: $8
- Children under 12: free
- Ticket plus tote: $10
- Four-ticket bundle: $20, which works out to $5 a person for a group of four
The trolley runs only on Saturday. If the full loop is too much for one day, you can ride the trolley Saturday for the shops on Damen and Ravenswood and walk to 4325 N Ravenswood on Sunday for the market.
How the $75 Actually Works
Unwrap Ravenswood is the part of the season that lasts the longest, and it's what makes the trolley's spread-out route pay off. From Black Friday, November 27, through Christmas Eve, shoppers who spend $300 at three or more qualifying businesses get $75 in local gift cards, paid as three $25 cards to Ravenswood businesses.
Read the rules before you start saving receipts:
- Boundaries. Qualifying businesses run from Clark Street west to Leavitt Street, one block west of Damen, and from Foster Avenue south to Irving Park Road.
- Three-business minimum. Your $300 has to come from at least three businesses.
- $25 per receipt. A receipt counts only if it's at least $25 before tax and tip.
- Grocery and liquor cap. Groceries and liquor count for up to $100 of the total.
- What doesn't count. Memberships, medication, legal or accounting services, postage, auto repairs, business-to-business purchases and gasoline.
- No gift receipts. Receipts aren't returned, so mail copies.
- One per household. Mail the completed form and receipt copies to the chamber office at 1770 W. Berteau Ave, Suite 101.
The rules connect back to the trolley. The $25 minimum means a coffee won't count, but a dinner, a gift or a service appointment will. The three-business rule rewards shoppers who move around. The boundaries are much bigger than the trolley route. The seven stops cluster between Montrose and Foster along Ravenswood and Damen, while eligible businesses reach east to Clark and south to Irving Park. That gives you a full month after Small Business Saturday to fill out the form with restaurant dinners and holiday errands around the area.
Rewards are limited and go to the earliest qualifying submissions. The chamber's two pages give different numbers and deadlines: the current Small Business Saturday page says the first 50 shoppers, and the Unwrap Ravenswood page says the first 75. Neither page lists a deadline for this season, so contact the chamber to confirm the 2026 cap and deadline before you mail anything. Because rewards go to the first qualifying submissions, sending yours soon after you reach $300 is the safer move.
The Second Saturday Moves to Wilson Avenue
Exactly one week later, on Saturday, December 5, the season moves a few blocks. The Ravenswood Neighbors Association holds its 7th annual Light Up Nights Festival and Holiday Market from 3 to 7 p.m. on Wilson Avenue between Ravenswood and Hermitage. It's free. The program includes live music, an indoor holiday market, food and drink vendors, professional ice sculpting, a kids' scavenger hunt, photo stations, a tree lighting, free hot cocoa while it lasts, a brass band, caroling, visits with Santa and a Chicago Chorus Girl performance.
The fundraising raffle benefits the association and the Ravenswood Community Services Food Pantry, and the gift baskets inside the market are donated by local Chicago businesses. All Saints Episcopal Church and the Greater Ravenswood Chamber of Commerce are partners.
The vendor list connects the two Saturdays. Hilary's Cookies, the pop-up at Hazel on November 28, is also listed for the Light Up Nights market. So are Fruit Cellar, Grunewald Arts, Lincoln Ice Cream Company, Mangel Florist + Surroundings by Colin, Monarch Beauty Farm, and others. A purchase at an indoor market stall may not qualify for Unwrap Ravenswood the way a storefront receipt does, so ask the chamber about it before counting on it.
A Sequence That Uses Both Weekends
Here's how the timing above fits together:
- Week of November 23: Check the chamber's page for the newly posted Small Business Saturday sales and download the Unwrap Ravenswood form.
- Saturday, November 28, by 11 a.m.: Start at Hazel on Montrose for the tote, then ride the trolley along Ravenswood and Damen. Save Dovetail for last, since its market runs until 6 p.m.
- Sunday, November 29: Visit the Chicago Artisan Market if Saturday ran out of time.
- Saturday, December 5, 3 to 7 p.m.: Light Up Nights on Wilson.
- Once you reach $300 across three businesses: Confirm the current deadline with the chamber, then mail the form and receipt copies to 1770 W. Berteau.
If you've noticed which Damen and Ravenswood Avenue businesses pull the longest lines this season and want to know what that means for your block, Chaz Walters will give you a direct, local read. Let's Connect.
