Endeavor Hotels Acquires Midway Portfolio for $68M, Plans Upgrades

If you want to see where the smart money is going in commercial real estate, look at the hotel sector right now. Especially in Chicago.

This week, Oakbrook Terrace-based Endeavor Hotels, led by Vishal Thakkar, picked up a portfolio of seven hotels and a restaurant near Midway International Airport for $68 million. The seller, RLJ Lodging Trust, paid $139 million for those same properties back in 2006. The math is stark. That’s a discount of more than 50 percent, a number that tells you more about the state of travel than any economic report.

I have walked through these airport corridor hotels over the years. They are functional. They are predictable. They serve a specific purpose for business travelers and tourists on a budget. Their value, however, has been completely rewritten.

Endeavor financed the deal with a $90 million mortgage from Access Point Financial. That loan is $22 million more than the purchase price. This is not a subtle move. It signals a clear intention to pour capital into renovations. Thakkar isn’t just buying buildings. He’s betting he can refurbish and reposition these assets for a market that has fundamentally changed.

The portfolio is a who’s who of mid-tier brands:

• 200-room Chicago Marriott Midway
• Hilton Garden Inn
• Courtyard
• Hampton Inn
• Others
• Combined total of 1,057 rooms

For RLJ, this sale is part of a broader strategy to shed older assets. For Endeavor, it’s a calculated wager on a recovery that has been uneven at best.

The broader context is critical here. Choose Chicago, the city’s tourism board, reports visitor numbers have clawed back from a devastating 73 percent plunge in 2020. About 57 million people visited the city in 2025. That is a solid recovery. But it still hasn’t reached the pre-pandemic peak of 61.6 million set in 2019.

More importantly, the composition of those visitors has shifted. Leisure travel came roaring back. Business travel did not. Corporations have permanently tightened their belts. Video conferencing is now a cost-saving fixture, not a temporary nuisance. This hits airport hotels and urban business-centric properties the hardest. Their revenue per available room, the industry’s key metric, has struggled to keep pace with rising operational costs.

This Midway deal is not an outlier. It is part of a pattern unfolding across Chicago’s hotel market, a pattern of distressed sales and deep-value plays.

Just this month, Toronto’s Manga Hotel Group paid $21 million for the former Royal Sonesta Chicago River North. That is a fraction of its past value. Another investor, Ketu Amin of Vinayaka Hospitality, is building an entire portfolio on this thesis. Earlier this month, he closed on the 520-room former W Hotel on Lake Shore Drive for $25 million. That property last traded for $126 million in 2012.

Amin’s strategy is a case study in sector timing. Last year, he bought the Hampton Inn/Homewood Suites on Michigan Avenue for $28.3 million. He picked up the Westin Michigan Avenue for $72 million, down from its 2018 price of $156 million. Then this year, he acquired the historic Blackstone Hotel for just over $43 million. It sold for $59.5 million in 2016.

These are not minor corrections. These are seismic repricings.

What these buyers understand is that the old valuation models are broken. A hotel’s worth is no longer tied to its 2019 performance. It is now anchored to a new reality of higher interest rates, reduced corporate travel, and inflated operating expenses. The calculus is about replacement cost. Can you buy an existing hotel for less than it would cost to build one from the ground up? Today, the answer is often yes.

For RLJ, selling at a steep loss is a strategic retreat, freeing up capital for newer properties in stronger markets. For Endeavor and investors like Amin, it is an opportunity. They are acquiring physical assets at a steep discount to historical prices, betting that their own operational expertise and fresh capital can squeeze out profit where the previous owners could not.

The risk is substantial. A recession could further suppress travel. Interest costs on that $90 million loan are real. But the potential reward is the creation of significant equity. If they can navigate this tricky recovery and wait for a more favorable debt market, these properties could be worth substantially more in five years.

This is what a market reset looks like on the ground. It is not about abstract economic indicators. It is about a Marriott on South Cicero Avenue selling for half of what it once did. It is about capital moving from one set of hands to another, based on a starkly different vision of the future. The hospitality industry is betting that the future, while different, is still worth checking into.