In Chicago, no one wants to be associated with Trump.
I was in Chicago last week for a work conference.
Before the conference started, I took an hour long boat cruise along the Chicago river, which was lovely.
The only drawback is TRUMP TOWER, the 3rd tallest building in Chicago is right on the river with his name overshadowing that section of the river.
However, one thing that amused me, is that underneath the building, along the Riverwalk, EVERY SINGLE ONE of the retail spaces was empty.
All along the Riverwalk are restaurants, bars, shops, boutiques, souvenir stores, etc. Almost all of them occupied. BUT NOT A SINGLE ONE was in use under Trump Tower. Just large "FOR LEASE" signs.
It made my heart smile.
= new reply since forum marked as read
Will Trump Tower’s Riverfront Retail Space Ever Get A Tenant?
RIVER NORTH — Donald Trump is back in the Oval Office and the Chicago Riverwalk is bustling.
And now, a global team of real estate brokers wants to seize the moment by leasing the retail space at Trump International Hotel and Tower that’s sat vacant since the skyscraper opened in 2009.
The Trump Organization has tapped Newmark real estate brokers in Chicago, New York City and London to search for retail tenants with the funds to build out the space and the stomach to operate underneath a 20-foot-tall “Trump” sign in a city the president has bemoaned as a “total disaster.”
The double-decker retail space at the base of Trump Tower, 401 N. Wabash Ave., has sat empty for 16 years — except for a hairdresser near the hotel lobby and a tour boat company docked near the building’s plaza. The 70,000-square-foot space holds the record for the longest-running Downtown retail vacancy over 5,000 square feet.
https://blockclubchicago.org/2025/08/11/will-trump-towers-riverfront-retail-space-ever-get-a-tenant/
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Last edited Fri Feb 27, 2026, 06:31 PM - Edit history (2)
I can see an argument that the plaza just to the north and east of the Trump building is Mag Mile adjacent: you can access it from Michigan Avenue. It's certainly not Gold Coast. (As I recall, they're trying to brand this area "North Bridge" with the signage, which is as goofy as calling Montrose to Lawrence west of Pulaski "Mayfair," like hoity toity you! )
The notion that teen takeovers scare business away from that specific area is goofy as hell, moreover, and answered well above: the business on the south side of the river (the actual Riverwalk, in my view) are booming during the summer, and the rest of River North / Streeterville is also fully leased out and quite vibrant (even if bro-ed out).
I would dispute the OP though: there are numerous businesses in the plaza area of the Trump building, though maybe not visible from the river cruises.
So, as usual, basically everyone is wrong about Chicago!
Yeah, like they don't have crime out in East Cornpone and up in Squalor Holler. Thank you for checking in from Meth Heartland.
