During one of her regular Sears shopping sprees, Kyra Dwyer picked out $150 of clothes for herself and her daughter. She was charged $18.

The 47-year-old is a member of Shop Your Way, Sears’s loyalty program. She regularly stopped at the store near her home in Fairfield, Conn., until it closed in January, on her way home from her work for the Coast Guard. She scooped up Craftsman tools, Lee jeans and a snowblower for her parents. Nearly all of the items were paid for with rewards points.

Fewer people shop at Sears these days. Of those who do, many leave with bags full of freebies, thanks to what is considered one of the most generous rewards programs in the business, one that persists, zombie-like, despite the company’s financial woes.

“Other retailers don’t even come close,” says Michelle Price, business-development manager for Hip2save.com, a deal-tracking website.

In the fall, Ms. Price bought sheet pans, a sauce pan and tights for a total of $36.77. After applying her Shop Your Way points and other rewards, her final tally: $0.