Luxury Homes for Rent in Chicago, IL (2,268 Rentals) Page 24 of 46

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The most luxurious Homes in Chicago with high-end amenities, features, and finishes.

property at 1815 N Milwaukee Ave
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
2 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

1815 N Milwaukee Ave, Unit 201

1815 N Milwaukee Ave
ChicagoIL60647
property at 360 E Randolph St
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
2 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

360 E Randolph St, Unit 25B

360 E Randolph St
ChicagoIL60601
  • Smoke Free
property at 1350 E Hyde Park Blvd
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

1350 E Hyde Park Blvd, Unit 2E

1350 E Hyde Park Blvd
ChicagoIL60615
property at 550 W Fulton St
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
2 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

550 W Fulton St, Unit 406

550 W Fulton St
ChicagoIL60661
property at 5300 N Mason Ave
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
3 Bedroom, 2.5 Bath Home for Rent
Available Now
Affordability

5300 N Mason Ave

ChicagoIL60630
property at 1452 W Winnemac Ave
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
3 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

1452 W Winnemac Ave, Unit 1

1452 W Winnemac Ave
ChicagoIL60640
property at 8 E Randolph St
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
2 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

8 E Randolph St

ChicagoIL60601
property at 41 E 8th St
$3,500 - $3,800
2 Bedroom Rentals
Available Now
Affordability

41 E 8th St

ChicagoIL60605
property at 400 W Ontario St
$3,500 - $4,890
2 To 3 Bedroom Rentals
Available Now
Affordability

400 W Ontario St

ChicagoIL60654
property at 230 N Michigan Ave
$3,550

Total Monthly Price

Base Rent$3,550
Total Monthly Price$3,550
1 Bedroom, 1 Bath Condo for Rent
Available Oct 5
Affordability

230 N Michigan Ave, Unit 2502

230 N Michigan Ave
ChicagoIL60601
  • Smoke Free
property at 823 W Montrose Ave
$3,575

Total Monthly Price

Base Rent$3,575
Total Monthly Price$3,575
3 Bedroom, 2 Bath Condo for Rent
Available Sep 15
Affordability

823 W Montrose Ave, Unit 3

823 W Montrose Ave
ChicagoIL60613
property at 111 E Chestnut St
$3,575

Total Monthly Price

Base Rent$3,575
Total Monthly Price$3,575
2 Bedroom, 2 Bath Condo for Rent
Available Oct 19
Furnished

111 E Chestnut St, Unit 35DE

111 E Chestnut St
ChicagoIL60611
property at 823 W Montrose Ave
$3,575

Total Monthly Price

Base Rent$3,575
Total Monthly Price$3,575
3 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

823 W Montrose Ave, Unit 1

823 W Montrose Ave
ChicagoIL60613
Showing Results 1151-1200, Page 24 of 46

Chicago, IL Area Reviews

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  • Cost of Living
  • Safety

Nicole • 4+ years in Chicago

April 10, 2026

Big city challenges with traffic but also provides the amenities of the city you can't find elsewhere

Frequently Asked Questions about Chicago

What type of rentals are currently available in Chicago?

There are currently 24137 Apartments for Rent in Chicago, IL with pricing that ranges from $600 to $43,181. There are also 5008 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chicago ranging from $700 to $58,000.

What is the current price range for Rental Homes in Chicago?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chicago ranges from $700 to $58,000 with an average monthly rent of $2,815.

How much are larger Three and Four Bedroom Rentals in Chicago?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chicago range from $695 to $38,481, while Three Bedroom Homes, Condos, and Townhomes for rent range from $700 to $40,000. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $1,025.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

Helpful Local Expert Guides

decorative image for The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago article

The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago

Written by: Nicole Harms

When choosing a place to live, there are many things you must consider. Your employer, your shopping preferences, and even schools are all important to think about. Yet cost of living is also important to know and plan for.

decorative image for Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible article

Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Written by: Nicole Harms

I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.

decorative image for Chicago Relocation 101: Mastering Utilities, Registration, and the CTA article

Chicago Relocation 101: Mastering Utilities, Registration, and the CTA

Written by: Nicole Harms

Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.

decorative image for Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago article

Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

Written by: Nicole Harms

From Lake Shore Drive to the O’Hare Airport, the city of Chicago is a study in diversity, resilience, and culture.

Articles, How-To's, and Tips

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags article

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.