Chicago’s Most-Expensive Homes For Rent

The luxury rental market in Chicagoland is small, but it boasts unique homes, including Michael Jordan’s former estate in Highland Park and one of the top floors of the St. Regis tower.

Inventory for high-end renters is “pretty low” and often comes from individual homeowners who need a renter to care for their home for a brief period of time, said Compass broker Janet Borden, who has experience with luxury rentals on Chicago’s North Shore.

Some of these high-end homeowners may have been trying to sell their homes and didn’t get the price they hoped for, so they decided to list it for rent instead, Borden said.

The owners of a Gold Coast townhouse at 1521 North State Parkway, for example, made this decision when they listed the 9,700-square-foot home for rent in 2024 after years of trying to sell it. The list price was gradually reduced from $10.3 million in 2018 to $7.3 million last year. The sellers switched gears and listed it for rent last year, first asking $30,000 per month and then $27,900 per month. It ultimately sold for $6.7 million, or $690 per square foot, in March.

In other situations, luxury homeowners are living elsewhere and looking for a tenant to care for the property until they want to move back in, Borden said.

In contrast to other segments of Chicago’s rental market, high-end rental deals are often struck off the market as owners and their brokers look for tenants who meet their specific needs and vice versa.

“It’s a little bit like a marriage, right?” Jameson Sotheby’s International Realty broker Linda Levin said. “You want to be very selective.”

The typical luxury renter is often someone who is being transferred to an area for work for a relatively brief period of time, ranging from a few months to a few years, Borden said.

“Some of the large companies bring in executives from other parts of the country and even from outside of the country,” she said. “That’s probably the biggest market for these kinds of rentals.”

Work transfers is also one of the main reasons why a luxury home might be available to rent, if its owner temporarily moved to another part of the country but wants to return to their forever home, Borden said. The trick is to match them up with a renter whose needs fall along a similar timeline.

She recently made this match on her listing at 1528 Sheridan Road in Highland Park, which is listed at about $13,000 a month and just received a verbal offer, Borden said.

Chicago’s luxury rental properties can command monthly rents of $30,000 or $40,000 a month, but listings are more common in the $10,000 to $20,000 range, according to public listing information. Most available inventory is either located at the top of luxury buildings downtown or in affluent North Shore suburbs.

At $150,000 per month, the property currently holding the title of Chicagoland’s priciest rental listing is in a league of its own.

2700 Point Lane, Highland Park – $150,000 / month

Michael Jordan’s former estate at 2700 Point Lane in Highland Park is asking $3.98 per square foot a month, according to public listing information.

Jordan sold the 37,700-square-foot property, dubbed Champion’s Point, to real estate investment executive John Cooper in December for $9.5 million, a significant discount from its first asking price of $29 million back when it first hit the market in 2012.

In Cooper’s case, putting the property up for rent is a way to capitalize on the prestige of the property and Jordan’s legacy. It was marketed at an even higher monthly rent rate of $230,000 for March Madness, the NCAA basketball tournament. The property will also be available for short-term stays through “Airbnb Luxe” – Airbnb’s collection of luxury offerings – as well as a separate website Cooper started to market the home, beginning June 30.

Cooper also plans to sell million-dollar time shares, giving buyers an annual one-week stay at the estate. For now, the home is available as an extravagant short-term rental, surrounded by a 97-acre nature preserve with wooded trails and close to the Skokie Valley Bike Trail.

@properties Christie’s International Real Estate Carrie McCormick has the listing.

255 North Green Bay Road, Lake Forest – $39,900 / month

Also on the North Shore, the Suffield House in Lake Forest is available for rent at $2.60 per square foot. The 5.4-acre property sold in November for $5.7 million, just above the last asking price of $5.5 million. It was listed for about $10 million in September 2022 before the price was reduced five times.

The seven-bedroom, 11-bathroom home spans 15,000 square feet and sits across from the Onwentsia Club golf course. The home was built in the 1930s by architect David Adler for Chicago meatpacking barron Lolita Armour.

@properties Christie’s International Real Estate broker Mona Hellinga, who is representing the home’s owner on the rental listing, declined to comment.

The St. Regis: 363 East Wacker Drive, Chicago – $35,000 / month

This 6,000-square-foot penthouse on the 89th floor has four bedrooms, four-and-a-half bathrooms and is listed for rent by Nancy Furth, an agent with the building’s developer, Magellan, at $5.83 per square foot.

The unit was listed for sale at just under $11.1 million ($1,850 per square foot) in May of 2019 before the offering was removed less than a year later. It was off the market for about five years before popping up as a rental in April.

The listing contains a disclaimer that the unit’s lease comes with a “90-day termination clause should the landlord decide to sell the property,” according to listing information.

Amenities include indoor and outdoor pools as well as a hot tub, fire pit, gym and an enclosed dog exercise area.

21 Lakewood Drive, Glencoe – $29,000 / month

Just like some homeowners rent their mansions they are trying to sell, others may rent out a recently purchased property until they are able to move in, Levin said.

Her client bought his lakefront mansion at 21 Lakewood Drive in Glencoe for $9.2 million at the end of April and is looking for a renter to live in the home until he is ready to relocate. The 8,600-square-foot home is available for $3.37 per square foot.

The custom-built home has five bedrooms and seven bathrooms and is a short walk from Glencoe Beach.

Levin used the cost to buy the property, most recently set by the market at $9.2 million or $1,073 per square foot, to determine the rent, she said. After it last traded hands, the home was briefly listed for monthly rent at $38,000 before its price was cut a month later.

451 West Superior Street, Chicago – $27,000 / month

Last on the list is a home in the sought-after River North neighborhood of Kingsbury Estates, available for $2.44 per square foot. The six-bedroom, six-bathroom home last traded for $4.5 million in the fall of 2021.

The home spans just under 10,200 square feet and includes a large rooftop deck and a three-car heated garage, according to public listing information.