Past meets future: In Chicago, 2025 property sales are rich in history

Historic buildings change hands every year, but 2025 stands out in Chicago for its lengthy list of commercial property sales with colorful ties to past business empires, pop culture icons and architecture luminaries.

The transactions are sure to add new chapters in a city that lays claim to the first skyscraper and is known as a U.S. property trailblazer.

A year of deals in the nation’s third-largest city provided a look back at times when newspapers and department stores were cash cows, and a signal of what's ahead for several properties that already have experienced dramatic change.

Here are some of this year's most significant real estate transactions involving buildings completed between the late 1800s and the 1920s.

North American Real Estate bought the retail space at the base of Tribune Tower for $62 million in June. It was the first sale as a retail-only property since the 36-story tower was completed in 1925 as home to the Chicago Tribune.

The sellers of the neo-Gothic tower were Los Angeles-based CIM Group and Chicago’s Golub & Co. The joint venture bought the tower for $240 million in 2016 and redeveloped office spaces on upper floors into luxury condominiums.

The city’s largest newspaper moved out in 2018.

The Chicago-based buyer took over retail space leased to tenants including the Museum of Ice Cream interactive experience, luxury watchmaker A. Lange & Sohne and a Blue Bottle coffee shop.

North American Real Estate is seeking tenants to fill the approximately 64% of the property that was vacant at the time of the sale.

The tower is at the southern end of the Magnificent Mile shopping district, sharing the Pioneer Court public plaza with an Apple flagship store along the Chicago River.

Tribune Tower, one of the city’s most recognizable structures, was created when owner Robert McCormick marked the newspaper’s 75th anniversary with an international contest to create “the most beautiful building in the world.”

The winning design, with a limestone exterior and flying buttresses, was submitted by architects John Howells and Raymond Hood. The tower’s facade includes fragments of famous properties from throughout the world, such as St. Peter’s Basilica, the Great Wall of China, Westminster Abbey and the Taj Mahal.

When billionaire Richard Branson kicked off his Virgin Hotels brand in 2015, it was in the 25-story Chicago landmark at 203 N. Wabash Ave. near the Magnificent Mile.

Just over a decade later, Virgin Hotels this June sold the 250-room hotel in the Old Dearborn Bank Building for just under $77.4 million. The sale came at an apparent loss to Virgin Hotels and Lionstone Development.

The buyer of the nearly century-old building was Accelerated Assets, a Birmingham, Michigan-based firm that specializes in converting properties to timeshare investments.

In September, Travel + Leisure Co. announced plans to open a Sports Illustrated-themed resort in the Art Deco building.

Travel + Leisure has an agreement to buy the property from Accelerated Assets in phases as it redevelops and sells off memberships in the sports-themed resort, according to online property records. In the first phase, Travel + Leisure paid just over $12 million for 24 of the property’s 250 rooms.

The Wabash Avenue building was designed by brothers C.W. and George Rapp, architects who were best known for ornate movie houses such as the Chicago Theatre, Oriental Theatre and Uptown Theatre. It was completed in 1928, and the building became a Chicago landmark in 2003.

The Old Dearborn Bank Building’s brick and terra cotta exterior is adorned with animals and mythical creatures.

Another newspaper palace, the former home of the Chicago Daily News, also changed hands in 2025.

Real estate billionaire Sam Zell owned the 26-story tower at 2 N. Riverside Plaza for about a half-century before he died in 2023 at age 81.

Chicago firms Blue Star Properties and the Wolcott Group bought it for $27.75 million in July, and they plan extensive renovations to modernize the Art Deco structure.

The sale price was well below the value of a $65 million loan that a Voya Investment Management affiliate provided Zell in 2016.

The 98-year-old tower will remain offices at a time when many historic office properties are being converted to new uses such as residential.

New owners plan upgrades to the lower-level concourse leading to commuter trains and the huge outdoor plaza along the river. Activities such as live music and farmers’ markets are planned on the plaza, with new food, beverage and retail tenants bound for the concourse.

A new second-floor amenities area will include a lounge, bar, coffee bar, four-lane bowling alley, music room, billiards table and auditorium, Blue Star President Craig Golden said. New office tenants are sought to fill hundreds of thousands of square feet of vacancy.

Those changes are less dramatic than some contemplated in decades past by Zell, who floated but never acted on various plans that would have razed the building or added another tower alongside it.

Zell bought the tower in the 1970s and moved his office there in 1982, leading several prominent real estate investment trusts from an office that extended to an outdoor terrace and garden overlooking the river.

Construction of the tower Holabird & Root-designed tower was completed in 1929, just before the start of the Great Depression.

Journalists such as Carl Sandburg and Mike Royko wrote for the now-defunct Chicago Daily News while it was based in the building.

The 2.4-acre property is known for several Chicago development firsts, including using air rights to build over train tracks.

Another property that Zell had owned for about a half-century, the Cobbler Square Lofts apartment complex in Old Town, was sold for $86.65 million to a key player in Zell’s biggest real estate deal.

Former Blackstone real estate executive John Schreiber’s Centaur Capital Partners bought the 292-unit property at 1350 N. Wells St. in January. Centaur’s partner on the deal is Chicago-based JDL Development.

Schreiber, based in north suburban Lake Forest, helped launch Blackstone’s now-sprawling real estate business. He was a top executive for the private-equity giant when it bought Equity Office Properties Trust, a Zell-led real estate investment trust, for $39 million in 2007.

Cobbler Square began as a factory for Western Wheel Works, then the world’s largest bicycle maker, in the 1880s, according to materials from JLL, which brokered the sale for Zell’s estate. It was later converted to a Dr. Scholl’s shoe factory. Investors including Zell converted the property, which includes structures ranging from three to five stories tall, to apartments in the 1980s.

After completing the purchase, JDL CEO Jim Letchinger said the new owners plan to overhaul each unit as tenants move out, while also making improvements to amenities such as outdoor courtyards and the fitness center. A swimming pool is planned within the large, main courtyard to make it a gathering area, Letchinger said.

The venture also could add a new five-story apartment or condo building on vacant land in the complex or atop the existing parking garage, Letchinger said.

The Briar Street Theater building in Lakeview on the city’s North Side was home to a nearly three-decade run of concerts by the Blue Man Group before the bald-headed, blue-dyed musicians’ residency ended in January.

Local developer JAB Real Estate bought the two-story building at Halsted Street and Briar Place for $6 million in October. The firm plans to add to the top and side of the structure to create 66 apartments, retail and amenities, including a roof deck and fitness center.

The approximately $25 million project will be called the Higgins, adding to a list of building conversions throughout the city to apartments from other uses amid strong rent growth and a shortage of housing. The redevelopment will add three stories to the current two-story structure starting in early 2026, JAB Managing Principal Frank Campise told CoStar News.

Built in 1901, the building began as stables for horses that the Marshall Field & Co. department store chain used as part of its delivery service. It was later used by a storage and moving company before Walter Topel bought it in 1970 and converted it to a theater.

The Blue Man Group began its residency there in 1997. Topel died in 1987, but his family had continued to own the property until the sale to JAB.

The conversion plan first became public in May, and a zoning change was approved by Chicago’s City Council in July after 44^th Ward Alderman Bennett Lawson gathered public input.

The seven-story building at 230 E. Ohio St. sold for the second time in as many years, setting up a conversion from loft offices to 72 apartments.

Horizon Realty Group last year bought the Streeterville building for $5.6 million, which plans for a residential conversion.

After completing some interior demolition and moving out remaining office tenants, Horizon then flipped the property to another local firm for $9.75 million, in September. The new owner, Wildwood Investments, plans to carry out the residential conversion.

Designed by Alfred Alschuler and completed in 1917, the structure is named for William Nelson Pelouze, whose scale-making company used it for offices and storage, according to historical accounts.

Later, the building served as the longtime office of famed architect Ludwig Mies van der Rohe.

The brick building also served as the backdrop for the 1980s television series “Mary,” according to the Chicago Tribune. The exterior was the backdrop of the series, in which Mary Tyler Moore’s character wrote a column for the fictional newspaper based in the building.

The Ohio Street building just east of the Mag Mile is one of several smaller brick structures in downtown neighborhoods that in recent years have been targeted by developers for residential conversions.

In May, local developer Concord Capital bought a late-1800s building in River North that began as a shoe factory for $6.85 million. The firm plans to convert the seven-story building at 223 W. Erie St. into 66 apartments.

Concord Capital is looking to have the property added to the National Register of Historic Places, which could allow the conversion to be funded in part by historic tax credits.

The J.P. Smith Shoe Company completed the building in a then-industrial enclave known as “Smokey Hollow” in 1897, with an addition completed in 1899, according to a document submitted for National Register consideration.

The factory for J.P. Smith, once one of the largest shoe companies operating in Chicago, was designed by architect and engineer John H. Wagner.

The shoe company occupied the building until 1912, when it moved to a larger facility that it built about a mile to the west at 671 to 699 N. Sangamon Ave., according to the National Register document.

The Erie Street structure was used by several manufacturers and other businesses until 1980. More recently, it has been used as loft office space.

Arizona-based 3Edgewood, the real estate investment firm of Robert Sarver, entered Chicago with a deal for one of its widest office buildings, the former Montgomery Ward warehouse along the river.

The former owner of the NBA’s Phoenix Suns paid just under $88.7 million for the approximately 1.6 million-square-foot building at 600 W. Chicago Ave. That was a fraction of the $510 million that Sterling Bay and J.P. Morgan Asset Management paid in early 2018, about two years before COVID-19 upturned office values.

Department-store giant Montgomery Ward opened the building, which it called the Catalog House, in 1908.

Mailed-in orders were shipped to customers’ homes from the facility, which was so large that employees known as “pickers” would zip around on roller skates to gather items. Montgomery Ward also had offices in the 600-foot-long, trapezoidal building, according to a description of the property from when it became a Chicago landmark in 2000.

The building in recent years has been used as offices for tenants such as Groupon, the Big Ten Network, Echo Global Logistics, Tempus and Jump Trading. Until setbacks in recent years, the property was once close to being fully leased.

But Groupon’s financial woes and eventual move out from the building, as well as falling demand from tenants and plunging property values, led to a deeply discounted sale. The property was just 62.5% leased at the time of the sale, according to CoStar data.

3Edgewood said it plans upgrades such as carving out covered outdoor terraces within tenant suites and adding new food and beverage offerings.

A local firm’s purchase of the former Hollander Storage & Moving building in Logan Square renewed hope that a long-planned redevelopment of the vacant structure will come to fruition.

In March, J2 Equities paid nearly $4.8 million for the five-story building at 2418 to 2420 N. Milwaukee Ave. The seller was GW Properties, which owned it for nearly seven years but never moved forward with plans to expand the property and convert it to 62 apartments and ground-floor retail.

Completed in 1912, the building for decades was used by the moving company whose huge red billboard atop the structure served as an advertisement at the high-traffic intersection of Milwaukee and Fullerton avenues along side train tracks on the Chicago Transit Authority’s Blue Line.

Neighbors in recent years had worried that the building would deteriorate before it could be redeveloped.

J2 Equities CEO Jason Wiznitzer said his firm will carry out GW’s previous plan to preserve the main structure and demolish an adjacent single-story structure to make way for a new five-story building connected to the existing one.

Chicago developer R2 structured an unusual purchase of a seven-story brick structure along the edge of the Loop business district and Fulton Market.

R2 lined up bicycle parts maker SRAM as a tenant and joint-venture partner in the redevelopment of the long-vacant building at 550 W. Randolph St.

SRAM is expected to occupy about half the 168,750-square-foot building, which the partners bought for $14 million in November. It will be SRAM’s new global headquarters.

Seller W.P. Carey is in the process of selling off office properties throughout the world in a shift to industrial properties.

For SRAM, the deal will mean a move out of Fulton Market, where it was one of the first office tenants to lease space as the former meatpacking district transformed to a neighborhood of high-rises.

R2 and SRAM are seeking out one or more tenants to lease the remainder of the building.

The building was constructed in 1909 as a warehouse for medical products company MeKesson & Robbins, according to a brochure from Cushman & Wakefield, which brokered the sale. The company that originally occupied the building is now known as McKesson Corp.

From an auction, suburban businessman Marc Calabria bought the vacant eight-story building at 401 S. State St. for a tiny fraction of the $47.8 million in debt that the previous owner defaulted on.

Calabria, owner of Bloomingdale, Illinois-based IMC Accounting & Tax, paid $4.2 million for the property in October.

The new owner has not said what he has planned for the property that became a national landmark in 1976 and a Chicago landmark in 1997.

Completed in 1891, the building was designed by architect William Le Baron Jenney. He is known as a key figure in the building boom that followed the Great Chicago Fire of 1871 and for advancements that were used to create modern skyscrapers.

The property originated as a Siegel, Cooper & Co. department store before later spending decades as a Sears, Roebuck & Co. store.

Most recently, it was fully leased to Robert Morris University. The property fell into financial distress when that school moved out in 2020 and merged with Roosevelt University, which has other properties nearby.

Before the auction sale, the building last sold for $68.1 million in 2016, according to CoStar data.

Calabria also came to an agreement late in the year to buy the 18-story Railway Exchange Building, which was designed by Daniel Burnham and served as the storied architect’s office home.

Burnham was hired by the Santa Fe Railroad to create office space for it and other railroads after Burnham’s “White City” designs for the World’s Columbian Exposition in the late 1800s.

Completed in 1904, the Beaux Arts building at 224 S. Michigan Ave. is known for its terra cotta exterior and ornate lobby beneath a glass atrium.

Burham had an office in the building overlooking Michigan Avenue and Lake Michigan, according to the Chicago Architecture Center.

The University of Notre Dame Investment Office owned the building overlooking Grant Park for nearly two decades before handing it back to its lender, a subsidiary of New York Life Insurance, in January.

The transaction was a deed in lieu of foreclosure, a form of voluntary surrender of a property that allows the borrower and lender to avert lengthy foreclosure proceedings.

It’s unclear how much debt remained on a $47.5 million loan that Notre Dame borrowed in a 2015 refinancing.

The property is about 37% vacant, according to CoStar data.

New York-based 601W struck a deal to buy the sprawling office building at 175 W. Jackson Blvd. out of financial distress.

The firm, one of the biggest office landlords in Chicago, in the fall agreed to buy the more than 1.4 million-square-foot building designed by Burnham. The 22-story building was built in separate phases in 1912 — the year Burnham died — and 1927, according to JLL, which marketed the property for sale.

The wide-floor building went on the market for sale after Brookfield Properties defaulted on a $280 million loan and was hit with a foreclosure suit in 2022. The suit was filed by U.S. Bank, the trustee for bondholders of the commercial mortgage-backed securities loan.

Brookfield bought the building for almost $306 million in 2018 but stopped making loan payments in 2021, according to CMBS loan reports.

Between 2018 and 2024, the building underwent more than $24 million in upgrades to building systems, common areas and amenities, according to JLL. Vacancy in the building is 53%, a figure set to rise to 59% with move-outs to come, the JLL materials said.