Chicago is an imposing city, with massive skyscrapers, miles of waterfront, and all of the amenities you could ask for. It blends Midwestern grit with global sophistication, offering everything from world-class museums to iconic deep-dish pizza.
The Windy City’s housing market hasn’t been as turbulent as many of the other largest U.S. cities. Prices have risen steadily since 2012 – slower than the national average – helping the city remain relatively affordable. This has helped attract new residents, though a lot of newcomers choose to live in suburbs like Naperville. However, a growing housing shortage could throw a wrench into things.
Even with today’s economic uncertainty, the luxury housing market is still active in Chicago. Penthouse condos and 20th-century masterpieces make up most of the city’s high-end offerings, with a majority located in the Lincoln Park neighborhood.
Here were the most expensive home sales in Chicago in May, according to data from Redfin.
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Get prequalifiedThe most expensive home sales in Chicago: May 2025
1. 2210 N Orchard St, Chicago, IL 60614
- Sale price: $6,700,000
- List price: $7,450,000
On a triple lot in Lincoln Park, this 7,975-square-foot corner home offers space and privacy in the heart of the city. Highlights include 6 bedrooms, 5 bathrooms, a formal living room, dedicated office, media room, and gym.
2. 1841 N Orchard St, Chicago, IL 60614
- Sale price: $5,500,000
- List price: $5,850,000
This Chicago stunner on Orchard Street spans 8,380 sq ft with 6 bedrooms and 6.5 bathrooms. Also nestled on a triple-lot corner in Lincoln Park, it mixes grand entertaining spaces, a private library, gym, and media room.
3. 1845 N Orchard St, Chicago, IL 60614
- Sale price: $5,000,000
- List price: $5,495,000
This 8,380-square-foot Lincoln Park home has 6 bedrooms, 6 bathrooms, a wine room, media lounge, elevator, and 4-car garage. It’s in the same building as the previous home.
4. 1913 N Burling St, Chicago, IL 60614
- Sale price: $4,800,000
- List price: $4,990,000
Another home on one of Lincoln Park’s most coveted blocks, this 7-bedroom home offers over 6,300 square feet of custom living space. It comes with a private elevator, rooftop deck, and a yard built for entertaining.
5. 1721 N Winchester Ave, Chicago, IL 60622
- Sale price: $4,500,000
- List price: Unavailable
A custom home covering 6,400 square feet, with 5 bedrooms and 5 bathrooms. A private elevator, rooftop deck, and three-car garage are the highlights.
6. 56 W Huron St. Ph, Chicago, IL 60654
- Sale price: $4,500,000
- List price: $4,750,000
This 4,312-square-foot River North penthouse has 4 bedrooms, 4.5 bathrooms, and a private elevator opening into a dramatic two-story living space. Features include a chef’s kitchen, wet bar, and floor-to-ceiling windows.
7. 2140 N Seminary Ave, Chicago, IL 60614
- Sale price: $4,000,000
- List price: $3,950,000
This custom 5-bed, 7-bath Lincoln Park home spans 5,250 square feet with a barrel-vaulted kitchen, rooftop deck, elevator, and radiant-heated sidewalks.
8. 1237 W Wrightwood Ave, Chicago, IL 60614
- Sale price: $3,875,000
- List price: $3,950,000
Another Lincoln Park masterpiece, this home sits on an extra-wide lot and features 6 bedrooms, a high-end chef’s kitchen, and a spa-like primary suite. The lower level includes a rec room, kitchenette, and attached garage.
9. 2036 W Dickens Ave, Chicago, IL 60647
- Sale price: $3,800,000
- List price: $3,850,000
This new-construction home in Bucktown sits on a double lot and includes 7 bedrooms, 6.5 and bathrooms, and a three-car garage. It features a custom Italian kitchen, a spa-like primary suite, and multiple outdoor living areas.
10. 2550 N Lakeview Ave #2802, Chicago, IL 60614
- Sale price: $3,550,000
- List price: $3,300,000
This luxury 28th-floor condo in Lincoln Park boasts 3 bedrooms, 3.5 baths, and 3,030 square feet of open living space with soaring ceilings and panoramic views.
