For decades, the story of the Six Corners Shopping District has been one of nostalgia and hope — with just the right project, supporters were sure the Portage Park neighborhood could again be the city’s premier shopping destination outside the Loop.

With new businesses and restaurants opening, supporters say Six Corners’ time is now — but obstacles remain, with the fate of several high-profile properties in limbo.

The transformation of the district — which lost its luster amid the rise of suburban shopping malls — has been “on a really good roll,” said 45th Ward Ald. John Arena, who has worked to transform it into an arts and culture mecca since he was elected in 2011.

But before Six Corners regains its former glory, the fate of the last Sears store in Chicago as well as the future of the Portage Theater must be resolved — and something will have to fill the open pit that now sits at the heart of the shopping district at Irving Park Road, Cicero and Milwaukee avenues.

“I see them as opportunities, not missing pieces,” Arena said.

When Sears opened its store at Six Corners on Oct. 20, 1938, more than 99,500 customers poured into its aisles — it was the first Sears to be air conditioned, according to news reports.

Nearly 80 years later, the Sears at Six Corners is the last Chicago store standing. But with Sears $1 billion in debt, it is an open question how long it remains.

Howard Riefs, a spokesman for the Hoffman Estates-based firm, said in a statement that Sears plans “to continue to serve our members and customers on Chicago’s Northwest Side as we have for the last eight decades.”

However, Sears sold the land the store sits on to Seritage Growth Properties in 2015 in a sale-leaseback transaction that gives Seritage the right to “recapture” the land, Riefs said.

“To date, we have not received notice from Seritage that they will be exercising that right,” Riefs said.

Local officials hope as one of the few remaining department stores on the Northwest Side, it will hang on at least a while longer.

If the fate of Sears is an open question, the land across Irving Park Road along Milwaukee Avenue is an open pit — and has been since late 2016, when a Bank of America branch was torn down to make way for what was to be a shopping center anchored by Aldi’s and Ross Dress for Less.

In June 2014, Clark Street Development paid more than $10 million for the land and a parking lot; it won Arena’s support for the 100,000-square-foot shopping center in February 2016 — despite residents’ complaints that the proposed tenants were not upscale enough.

After tearing down the bank, progress stalled — and the developer told Arena the project as originally proposed wasn’t economically feasible.

Peter Eisenberg, a principal with Clark Street Development, declined to discuss the project.

Arena said he encouraged the developer to partner with a residential housing developer and reduce the size of the shopping center.

The success of another nearby project has “proven the hypothesis” that people want to come to Six Corners to shop and eat, Arena said.

That involves another Bank of America that was to be torn down. Instead, Arena worked to preserve the block-long building at Irving Park Road and Lamon Avenue.

The building is now home to Binny’s Beverage Depot and a Retro Fitness gym — and next door, the North Side’s first Culver’s.

That development helped the entire stretch of Irving Park Road hit a “tipping point,” Six Corners Association Executive Director Kelli Wefenstette said.

“It feels like it changed overnight,” Wefenstette said. “That entire block has come alive.”

Three new businesses have opened in the Portage Theater building in recent months. The building was sold in 2016 to a suburban real estate investment firm that has refurbished all 34 apartments above the theater.

The theater itself — a 98-year-old throwback to the era of movie palaces — remains shuttered as its owners search for a new operator.

Arena is confident the theater’s new owners will restore the theater to its former glory: “It will be the gem that it used to be.”

Joining Distinct Bath and Body Shop in the theater building will be the Frunchroom, opening in early April. Fischman’s Bottle Shop has been open since November, thrilling beer aficionados. Fischman’s Liquors Public House, which promises outdoor seating, is opening this spring.

“That is going to change the whole corner,” Arena said. “Just you wait.”