This month's bombshell $550M deal for 1 N. Wacker Drive marked one of the priciest office deals in the U.S. in 2026 and a potential turning point for a Chicago office market that has largely been defined by bargain-bin buys over the past few years.

The $392-per-SF price of Zara founder Amancio Ortega’s acquisition dwarfs every large office sale in Chicago since the start of 2024. It also marks the first time a property over 700K SF has appreciated in a trade during that period, according to data from CRE analytics platform Lightbox.

“One North, just by the nature of its sale, has made people question, ‘Wow, I thought I had left Chicago for dead, and now look at this, $400 per SF,’” Lightbox Head of Data Strategy Manus Clancy said.

Clancy said the Ortega buy is indicative of what he’s seeing in top-shelf office sales across the country: Premium properties can still nail a premium price. New York City's Park Avenue Tower sold for $730M in January, and San Francisco's Transamerica Pyramid traded for $691M in April.

Still, the Chicago office market has largely featured significant discount sales in the past few years. The average discount across the office sales above 700K SF with a previous sale price was 71.4%. Those sales totaled $1.2B, compared to $4.5B when the properties were last sold.

Sales of the scale of 1 N. Wacker give potential sellers on the sideline a “bona fide comp” at the top of the market that can instill confidence and potentially push them to move other properties of that tier, Clancy said. Owners who may have been staring down major investment to upgrade a property’s amenities, common areas and unleased space may reconsider.

The sale also presents an alternative path instead of a sale with the intention of office-to-residential conversion, Clancy said.

“People are now kind of rubbing their chin, saying, ‘Hmm, office-to-resi is not easy. Maybe office-to-better-office is the way to go,’” he said. “That's where the calculus changes with this big Zara owner sale.”

But the sale doesn’t move the floor for Class-B and C offices, Clancy said. There have been enough transactions at that tier of the market that investors know the expected price point, roughly between $40 per SF and $70 per SF.

“The have-nots are faced with taking their castor oil, if you will, taking their medicine, or trying to play out a conversion play,” Clancy said. “I don't think there's anything with this sale that turns that.”

A potential turning point for those owners could be a scenario where artificial leasing reaches the heights of the tech leasing boom, Clancy said. If a situation arises where AI companies need so much space that they have to settle for buildings below the top-shelf properties, it could provide a boost to older office towers.

What if an AI leasing boom doesn’t bear fruit?

“We’re stuck in the marsh,” Clancy said.

To see another office sale of this magnitude in the city, Clancy said it may take investors believing in a tech leasing boom and the returns from investing in an “A-minus” office property.

“These things can change on a dime,” Clancy said. “If you get a firm like an Anthropic coming in tomorrow saying, 'We want 300K SF in downtown Chicago. We want to expand our footprint.’ The winds can change very, very quickly.”