Most Expensive

Top 7 Most Expensive Rentals in Chicago

How much are you willing to pay in rent? $20,000 per month?

Sure you could get a house, but then you’re stuck! Take a look at some of the most luxurious (and most expensive) rentals in Chicago right now. $20,000 too far out of your price range? That’s okay, we’ve got rentals for under $9,000!

1. 6 N Michigan Ave, Chicago – $20,000

4 beds | 4.5 baths | 6,400 sq ft

2. 1150 N Lake Shore Dr, Chicago – $18,002

1 bed | 1 bath

3. 401 N Wabash Ave Unit 71E, Chicago – $16,000

3 beds | 4 full baths | 3,102 sq ft

4. 4 E Elm St Unit 6N, Chicago – $15,000


3 beds | 3 full , 1 half baths | 3,135 sq ft

5. 445 E North Water St Apt 2605, Chicago – $11,500

3 beds | 3 full , 1 half baths | 4,000 sq ft


6. 505 N Lake Shore Dr Apt 1112, Chicago – $10,000

4 beds | 3 full baths | 3,000 sq ft

7. 65 E Monroe St Unit 4726, Chicago – $7,470

3 beds | 2 full , 1 half baths | 2,490 sq ft





Most Expensive

10 Most Expensive Homes in Barrington, Illinois

Let’s get right to it—If you’re looking to spend a pretty penny, here’s a list of the 10 most expensive homes in the wonderful land of Barrington, Illinois.

11 Peraino Cir

$2,999,000 – 5 beds 6 baths 9,060 sqft

Is it a bird? Is it a European villa? Or just a magnificent Estate. From the stone fireplace to the home theater on the lower level, this home is nothing short of lavish. Also features a 2500+ bottle wine cellar, wet bar, exercise room, billiard room, locker room, rec room, poker room, and walk-in humidor.

90 Hawley Woods Rd

$2,675,000 – 7 beds 8.5 baths 14,607 sqft

This English Country Estate is surrounded by over 100-year-old oaks and conveniently located to highways, restaurants, as well as downtown Barrington. We also love the Master Bath’s custom walk in shower, jetted tub and his & her water closets. 

9 Goose Lake Dr

$1,739,000 – 4 beds 5 baths 7,000 sqft

This absolutely stunning French Country home sits at the end of the most wanted Goose Lake Drive. The End Of Most Desired Goose Lake Drive. The best feature of this home is probably the elevator which services all three levels. The sauna doesn’t fall too far behind, however.

17 Oakdene Dr

$1,285,000 – 4 beds 4 baths 3,527 sqft

A beautiful equestrian property, including a coach house, is tucked away in the popular Oakdene neighborhood. If you love horses, and a barn, this is the home for you. Paddocks, pastures, ponds & dressage area included.

74 Brinker Rd

$1,200,000 – 5 beds 8 baths 5,800 sqft

This very contemporary home is perfect for the socialite who loves to entertain. You can’t ignore a home whose insides are positioned around a central Atrium with an indoor pool. The lower level includes a Media Room, Wine Room, a Wet bar and tasting area, plus a large Exercise Room.

3 Jennifer Ct

$1,199,000 – 5 beds 4.5 baths 6,700 sqft

You’re not in the White House. It’s only the top 10 most expensive home at 3 Jennifer Ct. Surrounded by woods, and sitting on  a pond, the ample number of windows provides plenty of light and stunning views.

67 Brinker Rd

$1,150,000 – 5 beds 5.5 baths 4,894 sqft

Another English Country Estate in Barrington that sits high on hill, has recently been renovated and is now ready for purchase.  It’s centrally located to the Metra Train and the expressway, but nestled away on a private street.

7 Oak Lake Dr

$1,099,000 – 6 beds 6 baths 4,849 sqft

From the outsides manicured entryway to the beautiful, wood-aligned interior, this home in Barrington sits on a wooden lake front site with 16 rooms on nearly 5 acres.

15 Rolling Hills Dr

$995,000 – 5 beds 5 baths 8,396 sqft

This award winning home at 15 Rolling Hill Dr was presented by Home Builders Associate of Greater Chicago for excellence in home design. Surrounded by a myriad French doors, you’ll enjoy a range of tranquil views.

65 Hills And Dales Rd

$949,999 – 4 beds 4 baths 4,400 sqft

If you love to entertain, we think you’ll love this house. There’s a space to entertain, and  very separate space to live, thanks to the design layout of this home. The home is in seclusion on over 5 acres of land, a circular driveway, and a 3-car garage.


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7 Most Expensive Homes for Sale in Chicago

It’s not surprising that the seven most expensive homes for sale in the city would likely be found on the tranquil streets of Lincoln Park or within the bustling confines of the Gold Coast. These are the homes that’ll make you go “ah!” when you see them and “yikes!” when you hear the price.

1932 N Burling St • $50,00,000

The most expensive home in Chicago, there are plenty of manicures to go around when we talk about this gem. From the water fountains to the antique pavilion, there are 6 beds, 7 full and 4 half baths in this 25,000 square-foot package.

58 E Chicago Ave •  $18,000,000propertyproperty2

This Victorian building with the second oldest elevator in Chicago is completely available. It comes with three commercial spaces and 25 residential units, but you are free to reinvent the existing structure or build from the ground up (that is, if you come with the coins).

1909 N Orchard St • $15,500,000

One of the most recognizably, picturesque streets in the city, adjacent to the infamous Lincoln Park High School, there are 6 beds, 6 full and 2 half baths, and 14,000 square foot.  It also doesn’t hurt that the house is pretty darn pretty.

9 W Walton St Unit 3500 • $12,950,000

There’s always something presidential about a white house, and this condo is not too far from it. With amenities like a motor court with a valet, an indoor spa pool, a two-story exercise studio, and a wine tasting room, it’s hard to say no. Unless, somehow, you were not willing to spend nearly $13 M.

1336 N State Pkwy • $12,500,00gold coast

How could you not respect a house next to a house that winds up being larger-than-life when you walk inside? This elegant and historic Georgian home wold require a sophisticated taste and a pretty penny.

401 N Wabash Ave Unit 87 A • $12,500,000

Views cost, and with views like this, they just might be worth the pretty penny. With floor to ceiling windows in this 6,850 square foot penthouse, it’ll be hard to not give up $12.5 M, right?

800 N Michigan Ave Unit 60PHN • $12,000,000

A very modern penthouse at the Park Hyatt, plus unobstructed views from the north, east, and west, you’ll get access to a private elevator with this buy. It’s hard to think this pad comes with just 2 beds, 2 full and 1 half  baths.