President Donald Trump’s real estate firm has landed its first retail tenant for his namesake skyscraper along the Chicago River, ending a 17-year drought in what has been one of the most challenging spaces to fill in the city.
Local restaurant Prasino Cafe has leased about 2,800 square feet at the base of Trump International Hotel & Tower, owner Ted Maglaris said.
The lease fills just a small portion of the approximately 70,000 square feet of never-used retail space at the Riverwalk and mezzanine levels of the property at 401 N. Wabash Ave. that Newmark brokers were hired by the Trump Organization to find tenants for in May 2025.
'Take politics out of this and it’s some of the best space in the city and the entire country.'
Yet it represents the first deal in space that, despite its prominent location overlooking the river and steps from North Michigan Avenue shopping, has remained unused since the residential and hotel tower opened in 2009.
Previously futile efforts to fill the space for years have been a topic of conversation among Chicago real estate professionals and residents.
That is in part because it is the city’s second-tallest skyscraper at 1,389 feet tall. It trails only Willis Tower, the former Sears Tower, at 1,451 feet.
High-profile space
In recent years, the vacant space also has stood out because of the polarizing nature of the property’s developer, Trump, now in his second term as president.
“Take politics out of this and it’s some of the best space in the city and the entire country,” Goldstreet Partners broker David Goldberg, who represented Prasino in the lease, told CoStar News. “Trump or no Trump, Chicago wants to see this space filled.”
Prasino first opened in suburban LaGrange, Illinois, in 2009, the same year that Trump Tower was completed.
The restaurant’s name means “green” in Greek, a reference to fresh ingredients used in foods such as salads, bowls and wraps.
Prasino has previously opened, and later closed, restaurants in other suburbs and in Chicago’s Wicker Park neighborhood.
In deals announced last year, Prasino is set to open this summer at the base of residential towers in the Loop and Fulton Market as part of plans for continued expansion.
Trump Tower spells out the name of the real estate developer and reality television persona turned U.S. president in 20-foot-tall letters on lower floors. The building is the scene of frequent anti-Trump protests, leading to barricades sometimes limiting access to a walkway along the property.
Access to the property and other aspects of its layout have long been considered by retail experts to be obstacles to filling the space.
Luring tourists
But Prasino liked river-level space at the eastern edge of the property because of its proximity to tourists boarding river boat tours, providing access to hungry customers and outdoor seating.
“I’ve always been drawn to this area because of the river and the energy that comes with being near the water," Maglaris said in a statement to CoStar News. "It felt like the perfect setting to bring a Mediterranean and Greek-inspired concept to life — something that feels fresh, vibrant and rooted in that coastal lifestyle. There also weren’t many opportunities left along the riverfront because those spaces are going quickly, so when the right opportunity came at the right time, along with the right deal, it made the decision easy.”
'Those spaces are going quickly, so when the right opportunity came at the right time, along with the right deal, it made the decision easy.'
The restaurant is expected to open in spring 2027.
The Trump Organization did not respond to a request for comment on the deal from CoStar News.
Goldberg described the Prasino deal as an extension of dining along the river, where several high-grossing restaurants have opened at the base of skyscrapers in recent years.
“All that retail space is a continuation of some of the most amazing restaurants in Chicago — RPM Seafood, Chicago Cut and Smith & Wollensky,” Goldberg said. “This space has sat vacant for so long, and now it’s getting activated.”
Trump criticizes retail stretch
Although the Chicago tower is the tallest ever developed by Trump, the Republican president has frequently criticized the Democratic-leaning city.
Just months after the latest effort to fill the retail space was launched, Trump late last year ranted in a late-night social media post against Chicago’s “Miracle Mile Shopping Center,” which he described as failing and “ready to call it quits” without military intervention.
Chicago and U.S. real estate professionals were left scratching their heads since there is no shopping center or area of the city by that name, but the statement appeared to be aimed at the mile-long section of Michigan Avenue often referred to as the Magnificent Mile.
The Mag Mile endured closures and record-high availability in recent years before a recent run of high-profile leases has left large tenants left to compete for remaining spaces.
Recent openings or announced deals include a Harry Potter-themed store, a first-of-its-kind space celebrating the history of candy called the Candy Hall of Fame Experience, a $50 million magic venue called The Hand & the Eye, the return of Japan’s Uniqlo, a deal for a three-concept flagship from American Eagle Outfitters, a Levi’s relocation and talks by Nike to move its longtime flagship to another space down the street.
Challenges remain, including large vacancies in malls on the avenue and the closure of a massive Saks Fifth Avenue store.
The owner of one property with high vacancy, the Water Tower Place vertical mall, recently unveiled plans for a $170 million overhaul.
For the record
The tenant was represented by Goldstreet Partners broker David Goldberg. The landlord was represented by Newmark brokers James Schutter, Larry Kling, Jason Pruger, Jason Stein, Tim Newman and Simon Carson.