Hotel investors have been snapping up resorts and other leisure-oriented properties, the biggest beneficiaries of the recent spike in vacation travel.

Now, a handful of city-center hotels are hitting the market, testing whether the rebound in hotel sales can extend to properties that cater to corporate travelers and that are still suffering from the sharp decline in that business.

The latest to gauge investor appetite is Chicago’s storied Drake Hotel. The owners are hoping to get more than $250 million for the 535-room property, say people familiar with the sellers’ thinking. But some analysts suggest that will be a challenge given the tough market conditions for urban hotels right now.

Nonetheless, a few other urban hotels are also testing the market. In Boston, Brookfield Asset Management is marketing the Kimpton Nine Zero Hotel in Boston, while in Chicago, the 178-room Talbott Hotel is on the block.

Most of the lodging industry’s recent high-profile deals have been for resort properties that have thrived as pent-up demand for leisure travel kicked in this year, especially at some luxury hotels. Nearly $19 billion worth of U.S. hotels sold in the first seven months of 2021, compared with $8.5 billion during the same period in 2020, according to CoStar Group Inc.

Host Hotels & Resorts Inc. agreed to pay $610 million in May for the 444-room Four Seasons Resort Orlando, a record price in that market. Sunstone Hotel Investors Inc. recently purchased the Montage Healdsburg in California wine country for $265 million, or about $2 million per room key, making it one of the most expensive U.S. hotel sales by that metric ever.

By comparison, hotels operating in mostly empty city centers look risky in the current business climate but could turn out to be a bargain if corporate travel bounces back, analysts say.

“If you’re a buyer of hotels, and you can’t get the pricing you want, you move down the list of markets you may be willing to invest in because everyone is chasing these other deals,” said Michael Bellisario, a Baird Equity Research senior analyst.

The hotel market in Chicago has struggled during the pandemic, though it has shown some signs of life more recently. The city’s occupancy rate stood at 60.2% during the first week of August, a big improvement from 25.3% the same week of 2020, and not too far below the national average of 68%, according to hotel-data business STR.

But now the new variant of the Covid-19 virus threatens to snuff out any budding rebound in Chicago and other big cities. Businesses are postponing plans to reopen offices and groups are calling off events. This month, for example, organizers of the New York International Auto Show and the New Orleans Jazz & Heritage Festival said they were canceling.

“For the downtown property, without the sustained recovery of business travel and the corporate-meetings market, that’s going to be tough sledding for a while,” said Jan Freitag, national director of hospitality analytics at CoStar Group Inc.

The Drake, which is located on a luxury-retail section of North Michigan Avenue known as the Magnificent Mile, stayed open throughout the pandemic. But it needs a major upgrade, which would require tens of millions of dollars in additional investment from a buyer, according to people familiar with the property.

Many of the rooms could be converted into high-priced condominiums, retail space could be added, and the lodging overall could be restored to its former glory, said Adam McGaughy, a senior managing director of JLL, which was hired to market the majority stake.

“The way we are selling this is more of a pure real-estate and redevelopment play as opposed to a price per pound of hotel space,” he said.

The Drake opened in 1920. Its guests have included Charles Lindbergh and Princess Diana. Chicago’s Brashears family owns a majority stake in the hotel. About 30 years ago, it sold a long-term lease on the property but kept ownership of the underlying land.

Last year, the ownership was restructured partly because of the pandemic, eliminating the leasehold position and giving the Brashears and others ownership of the entire property.

Write to Peter Grant at peter.grant@wsj.com