Summer sidewalk sale time can bring deals for you, big bucks for store owners

As summer heats up in Chicago, so do sidewalk sales.

They’re more than an excuse for store owners to soak up some rays. Some say a weekend-long event can bring in the equivalent of a month’s worth of revenue.

And it’s not as simple as unfolding a table, arranging sale items and waiting for people to show up and spend their money. Some shopkeepers prepare for weeks or months for what can be their most important event all year.

Hyde Park Summer Sidewalk Sale

July 18-20, 1500 block of East 55th Street

Wesley Shoes, a Hyde Park store that has been open since the 1965 gets a big boost from its kiosk at the Hyde Park Summer Sidewalk Sale, held in the courtyard of the Hyde Park Shopping Mall at East 55th Street and South Lake Park Avenue.

“July is typically a very slow month because people already have their summer shoes, and it’s kind of a transition month before we get to back-to-school,” says store owner Bruce Wesley, who has been participating for more than 40 years. “But we always get a spike in business for the sidewalk sale.”

Wesley says his business is based on service and relationships, that he’s fitted shoes for generations of families and also sold to Malia and Sasha Obama and Eric Clapton.

But the sidewalk sale attracts bargain-hunters, which introduces the store to new customers. Wesley says it’s the one time of year he really marks shoes down and competes on price.

“It’s kind of like a ‘last call’-type situation,” he says. “You could expect anywhere from about 40 to 60 percent off.

”I’m not going to try to beat Amazon or whatever, but people know that we have good, quality shoes. . . . When we do markdowns, it’s real markdowns.”

Wicker Park Bucktown Summer Sidewalk Sale

Aug. 24-25, along Damen Avenue, Milwaukee Avenue, North Avenue and Division Street.

Virtu

In Bucktown, Julie Horowitz-Jackson says Virtu, her jewelry and greeting card shop, has participated in the Wicker Park-Bucktown Summer Sidewalk Sale for 15 years, since the first one took place. That was three years after she opened the store on North Damen Avenue.

Horowitz-Jackson says she gets creative with deals to try to bring back repeat shoppers. Her jewelry pieces normally cost up to $550. But she offers bags of some jewelry for $25 during the sale.

“For the first three hours, there’s nothing but mayhem of people scouring through the bags and trying things on, trading, passing things back and forth,” she says.

Horowitz-Jackson says she spends a lot of time preparing for the sale, usually working for four straight Mondays — when the store is closed — to get ready, but that it’s worth it.

“I would say that the weekend of sidewalk sale can sometimes equal an entire month of business,” she says.

Andersonville Sidewalk Sale

July 26-28, 4800 to 5800 blocks of North Clark Street and adjacent side streets

Sarah Hollenbeck, co-owner of Women & Children First bookstore in Andersonville, says the money made from taking part in the Andersonville Sidewalk Sale supports the store’s nonprofit Women’s Voices Fund, which pays for most of the store’s author readings and signings.

The sale is the one time of year the store sells used books, accepting donated books starting in the spring, pricing them from $1 to $3 and usually bringing in more than $5,000.

Andersonville Chamber of Commerce

“It’s a really good vibe on the street,” Hollenbeck says. “Just browse the different sidewalk sales, listen to music and then go out to dinner on one of the patios.”

Alamo Shoes has been a fixture at the neighborhood event for over 40 years. Owner Richard Alamo says it’s his busiest four days of the year, “really our Super Bowl event. It’s one of the few times a year that I actually strategically plan for.”

Alamo says he searches for good deals to bolster his inventory, designs fresh advertising, sets and resets prices and enlists his whole family to help out because his business doubles during the four days of the sale.

“If my daughter told me she was getting married on the Saturday night of sidewalk sale, I would say: ‘You have to change your date,’ ” says Alamo.