Ashkenazy Buys Suburban Chicago Shopping Center for $60 Million

Ben Ashkenazy just placed a major wager on suburban retail by paying roughly $60 million for Orland Park Place southwest of Chicago, cementing its shift in focus from the city’s downtown shopping scene and into the suburbs.

The roughly 600,000‑square‑foot open‑air shopping center on 45 acres in Orland Park now belongs to the New York-based investor’s firm Ashkenazy Acquisition, which acquired it from New Orleans-based PMAT Real Estate Investments, Crain’s reported.

The buyer has spent recent years tangled in turbulence on downtown Chicago’s downtown retail strip only to pivot decisively toward the suburbs. In September, Ashkenazy’s partner Aurora Capital Associates ironed out a $98 million debt package that was coming due in order to keep control of the 300,000‑square‑foot retail chunk at 700 North Michigan Avenue on the Magnificent Mile. While it’s unclear whether Ashkenazy’s ownership stake was changed by the transaction, the firm’s focus in the Chicago area has been transitioning away from the urban core.

Ashkenazy this year raised a $750 million war chest for acquisitions, largely from his own funds with backing from prior investors, to target retail and hospitality assets — especially those with overleveraged owners forced to sell at steep discounts.

That capital may now be deploying into properties like Orland Park, where a strong tenant roster and affluent suburban catchment area offer a steadier cash‑flow story than distressed downtown retail. Ashkenazy also purchased a retail property on Chicago’s Far North Side near Evanston in 2023 for $22 million.

Orland Park Place’s mix of national retailers, discounters and steady foot traffic stands in contrast to the volatility that’s plagued large downtown retail landlords, many of whom have wrestled with tenant departure, loan defaults or writing off underperforming assets.

For Ashkenazy, the purchase may signal a recalibrated retail thesis: rather than double down on vertical retail in a troubled downtown — where the firm already defaulted on a $61 million loan tied to another Magnificent Mile asset in 2024 — it is quietly building a suburban platform anchored by stable shopping centers.

PMAT initially purchased Orland Park Place for $74.6 million in March 2024, based on Cook County property records. Because the recent sale to Ashkenazy, as reported by the seller’s broker Mid-America Real Estate, did not encompass the outlots on LaGrange Road, the final price is estimated to be similar to what PMAT paid for the specific area included in the transaction, the outlet reported.

—Sam Lounsberry