Owners of the iconic Drake Hotel in downtown Chicago are putting a controlling stake of the 535-room property up for sale for the first time in more than 100 years, testing the U.S. hospitality industry’s recovery from the pandemic.

Until now, only partial interests in the hotel — where newlyweds Marilyn Monroe and Joe DiMaggio carved their initials into the Cape Cod Room’s wooden bar — have ever been sold.

The two majority owners of the hotel at 140 E. Walton St. are Phillips Martin Real Estate, controlled by Chicago’s Brashears family with 60% ownership, and San Francisco-based Acore Capital, with 30% ownership.

The two firms have hired JLL to offer the property for sale, calling it “a once-in-a-generation opportunity to redevelop one of Chicago’s most recognizable and prestigious landmarks.”

The Drake, currently branded as a Hilton Hotel, is being offered unencumbered of brand and management, offering the flexibility to reposition the site into its highest and best use, according to JLL, which said the remaining 10% is being marketed by another adviser. Phillips Martin and Acore did not immediately respond to requests from CoStar News for a comment.

The Chicago Central Business District is among the largest U.S. hotel markets and contains about 49,000 rooms spread across some 200 properties, according to CoStar data. The area is characterized by large high-end hotels. Over half the rooms are characterized as luxury or upper-upscale, the two property classes that have had the hardest time recovering from reduced business and convention travel due to the impact of COVID-19. The Drake is classified as an upper-upscale hotel.

The city core’s revenue per available room, or RevPAR, has declined sharply on a year-over-year basis, most recently down 67.8% as of June from April 2020. That’s an even steeper slide than the 54.4% drop in the overall Chicago market.

The last sale of an upper-upscale hotel in downtown Chicago occurred last fall, when the 364-room former Hard Rock Hotel, renamed the St. Jane Chicago and now a Pendry-branded property, sold for $65.6 million, or $180,192 per room, according to CoStar data. The last such sale before the pandemic was the 261-room Royal Sonesta Chicago River North that sold for $55 million, or $210,728 per room.

The historic Drake, which opened in 1920 and became “high society’s first choice in opulence” according to its website, features unobstructed views of Lake Michigan. A rooftop sign spelling out the name of the hotel in bright neon letters was altered in 2013 to feature LED lighting technology, slightly altering the pink hue that greeted motorists traveling south on Lake Shore Drive for 70 years.

The hotel offers nearly 220 feet of linear retail frontage along North Michigan Avenue, 36,900 square feet of flexible meeting space and various food and beverage options.

The JLL team representing the seller is being led by senior managing directors Adam McGaughy, Jeff Bramson and Danny Kaufman; managing directors John Nugent, Mark Stern, Amy Sands and Tom Kirschbraun; and Vice President Mark Jindra.