A cluster of seven hotels ringing Midway International Airport has changed hands for $68 million, a price that lands at roughly half what the seller paid for the same real estate back in 2006. Oakbrook Terrace-based Endeavor Hotels closed the deal for the portfolio, which also includes an adjacent restaurant property, buying it from Bethesda, Maryland-based RLJ Lodging Trust.
A Steep Discount on a Longtime Owner's Holdings
According to The Real Deal, RLJ sold the portfolio to Endeavor, whose principal is Vishal Thakkar, for $68 million — about 50 percent less than the roughly $139 million RLJ paid for the properties in 2006. The portfolio spans 1,057 rooms across seven hotels plus the restaurant parcel, and Endeavor financed the purchase with a $90 million mortgage from Access Point Financial, an Atlanta-based hospitality lender. That loan amount exceeds the purchase price itself, a detail public records suggest points toward planned property improvements, though the specifics of any renovation plans have not been detailed.
The properties sit clustered along South Cicero Avenue near the airport. The portfolio includes the 200-room Chicago Marriott Midway at 6520 South Cicero Avenue, the 174-room Hilton Garden Inn Midway at 6530 South Cicero Avenue, and the 170-room Hampton Inn Chicago-Midway at 6540 South Cicero Avenue, broken down as 133 standard rooms and 37 suites. Rounding out the lineup are the 104-room Holiday Inn Express & Suites at 6500 South Cicero Avenue, the 114-room Fairfield Inn & Suites at 6630 South Cicero Avenue, the 174-room Courtyard Chicago Midway Airport at 6610 South Cicero Avenue, and the 121-room Sleep Inn Midway at 6650 South Cicero Avenue. A TGI Friday's restaurant property at 6600 South Cicero Avenue was included in the sale as well.
Roots Tracing Back to a South Suburban Casino Deal
The hotels were originally developed by the Weglarz family, who sold the properties to RLJ in 2006. That same family later assembled land for the Wind Creek Casino in the south suburbs, selling that parcel to an affiliate of the casino's developer for $25 million in 2022. Neither RLJ nor Endeavor representatives responded to requests for comment, and the reason behind the portfolio's steeply reduced sale price remains unclear.
Part of a Wider Pattern of Discounted Chicago Hotel Sales
The Midway deal is not an isolated data point. Earlier this month, Toronto-based Manga Hotel Group paid $21 million for the former Royal Sonesta Chicago River North, while Vinayaka Hospitality, led by Ketu Amin, closed a $25 million purchase of the 520-room former W Hotel at 644 North Lake Shore Drive — a property that last traded for $126 million in 2012. Amin has also been active elsewhere in the city: he bought the Westin Michigan Avenue for $72 million in 2025, down from its $156 million sale price in 2018, and purchased the Blackstone Hotel for more than $43 million, compared with the $59.5 million it fetched in 2016. That Blackstone sale, previously reported by Hoodline, closed at about $43.2 million.
Chicago's broader tourism recovery has been uneven even as these discounted trades pile up. The city's visitor count collapsed 73 percent to just 16 million in 2020, and it still hasn't fully clawed back to the record 61.6 million visitors logged in 2019. Still, momentum has been building: Choose Chicago reports the city welcomed 56.8 million visitors in 2025, generating a record $21.5 billion in visitor spending and supporting 135,360 local jobs, with nearly 1.5 million more visitors than the year before. Ninety-two percent of leisure travelers surveyed said they plan to return within three years, per the same report — though business travel remains suppressed compared with pre-pandemic years.
Industry Forecasts Point to a Mixed Road Ahead
National hotel data suggests the broader market is still finding its footing even as leisure demand climbs. Per HVS, occupied room nights nationwide are forecast to finally surpass 2019 levels in 2026, though occupancy itself will still lag by roughly two percentage points once new supply is factored in. Average daily room rates remain well above pre-pandemic levels, HVS notes, even as rate growth is expected to moderate toward the end of the year. The firm also expects cap rates to rise amid higher interest rates, with only modest occupancy and rate gains anticipated by the close of 2027.
Vishal Thakkar brings more than 15 years of experience managing, developing and acquiring commercial real estate, according to Endeavor Hotels, spanning hospitality, multifamily and restaurant assets. Whether that experience translates into a turnaround for the Midway cluster remains to be seen, but for now, the sale adds another steeply discounted entry to Chicago's growing list of hotel trades well below what sellers originally paid.
