Chicago Luxury Rentals: Inside the $20,000-Plus Market

Ultra luxury rental offerings in Chicago are focusing on unique appeals and high-touch service, as the busy spring season approaches.

The pool of ultra luxury rentals in Chicago is small, but several have come on the market this year. Listing services show about 20 active rentals asking $20,000 in Chicago and the northern suburbs.

Renters in this tier are often corporate executives or athletes coming to the city temporarily, said listing agents who work with high-end rentals. People who bought a luxury home and are spending a year or two renovating it may also rent out a space in the city temporarily.

While the high-end rental market is insulated from some of the broader market dynamics, it still faces the same supply pressures seen in the for-sale market and lower-price rental markets, said Compass agent Melinda Jakovich LaGrange.

“Supply is down universally,” Jakovich LaGrange said. “We’ve had a lack of inventory of newer high-end luxury product. There’s been a lot of rental properties, but not necessarily the high end.”

Jakovich LaGrange is the listing agent for the most expensive public rental in the city currently, a $38,000-a-month house in Lincoln Park. The homeowners are listing it while they split their time between Chicago and Florida, she said.

The five-bedroom, 5,660-square-foot house at 441 West Deming Place sits next to the luxury condo building at 2550 North Lakeview Avenue, and renters have access to the building’s amenities, including a pool, fitness center and private park, Jakovich LaGrange said.

Target tenants for the home are high earners who want to get a taste of the city before buying a home, Jakovich LaGrange said. She said she’s seeing a rise in wealthy transplants bringing young families who want more space and privacy than an apartment can offer.

“There’s a whole new generation of wealthy people that might work in tech, AI, they can afford these rents,” she said. “And they probably would be buyers in a year or two. This is a great way for them to test the waters.”

Owners Sergey and Danijela Neckrysh paid $3.9 million for the property in 2018, property records show. They’re using another home in Chicago while in the city.

Amenities a draw in high-end rentals

At Optima Signature in Streeterville, a 52nd-floor penthouse is available for the first time publicly for $18,708 a month. The 2,352-square-foot, three-bedroom unit features a wraparound terrace and city and lake views, according to listing information.

The 57-story building at 220 East Illinois Street exemplifies the amenities race typical of high-end developments. David Hovey, Jr., president, COO and principal architect of Optima, said resort-level amenities are “the baseline expectation” for tenants in this market.

The building offers 1.5 acres of amenities across four floors, including pools, a fitness center, saunas, a basketball court and golf simulator. The penthouse also has access to amenities only available to renters in the building’s top 15 floors, including a lounge and rooftop sky deck.

“Residents with the financial capacity to rent a penthouse at this level also have the resources to purchase a home, but are choosing an apartment lifestyle driven by amenities, convenience, service and superior design,” he said.

At the St. Regis Chicago at 363 East Wacker Drive, the 86th-floor penthouse is up for rent for $35,000 a month. The unit is owned by Chinese investment firm Dalian Wanda Group, which was an early investor in the 101-story building, property records show.

Short-term rental company Blueground is listing many of the luxury rentals that came online this year. The company offers fully furnished apartments across Chicago at prices ranging from $20,000 to $30,000 for a one-month stay.

North Shore rentals offer break from city life

In Winnetka, a historic Art Deco mansion went back on the market Feb. 16 asking $50,000 a month in rent — the priciest active listing in the region. The North Shore is not known for luxury rentals, but its luxury for-sale market has been booming for the last few years, as wealthy buyers have increasingly looked outside the city. The Winnetka home is one of only three listings in the northern suburbs priced at over $20,000 a month.

The 8,000-square-foot, six-bedroom home is one of the most unique in the region, said listing agent Carrie Tarzon of @properties Christie’s International Real Estate. The mansion built in 1927 evokes the opulence of “The Great Gatsby,” with updated interiors that include a checkered black-and-white tiled chef’s kitchen and a custom blue-lacquered family room.

The owner, Keith Rudman, bought the mansion in 2020 for $3.2 million. He remodeled and updated the interior before putting it up for rent in 2023, Tarzan said.

For Rudman, the listing isn’t motivated by finances as much as it is by appreciation for the home. Tarzon said he considers it a piece of art worth sharing.

“The homeowner realizes he owns something special, like he owns the Hope Diamond,” Tarzon said. “And he’s willing to share it with someone that has the means to live there.”

Tarzon said the target renter is a business executive staying in Chicago temporarily, or even for a few months at a time. She said she’s received interest from people bringing families who want an alternative to living in the city.

“They want to come back to the privacy, to the peacefulness of the North Shore and live in Winnetka and experience the culture of Winnetka,” she said.

North of Winnetka, Michael Jordan’s former home at 2700 Point Lane in Highland Park has been on and off the market for rent since it sold to real estate investor John Cooper in 2024 for $9.5 million. The home was listed for rent at $89,000 until Thursday, when it was taken off the market. It’s not clear if it was rented out or removed for another reason. Cooper has explored creative income opportunities for the famous estate, including a plan to sell $1 million shares of the property that Highland Park officials shot down, and a recent pitch to turn it into a tourist destination.