Luxury Homes for Rent in Chicago, IL (2,575 Rentals) Page 41 of 52

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

property at 3229 N Kenmore Ave

$5,150

Total Monthly Price

Total Monthly Price

Base Rent
$5,150
Total Monthly Price
$5,150

2 Bedroom, 2 Bath Condo for Rent

Available Aug 1

3229 N Kenmore Ave, Unit 3

3229 N Kenmore Ave
ChicagoIL60657
property at 2531 W Moffat St

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200
Total Monthly Price
$5,200

4 Bedroom, 3 Bath Condo for Rent

Available Sep 1

2531 W Moffat St, Unit 1

2531 W Moffat St
ChicagoIL60647
property at 5042 N Winchester Ave

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200
Total Monthly Price
$5,200

4 Bedroom, 3 Bath Home for Rent

Available Aug 1

5042 N Winchester Ave

ChicagoIL60640
property at 1241 W Oakdale Ave

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200
Total Monthly Price
$5,200

2 Bedroom, 2 Bath Condo for Rent

Available Aug 1

1241 W Oakdale Ave, Unit # 03W

1241 W Oakdale Ave
ChicagoIL60657
property at 429 W Grant Pl

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200
Total Monthly Price
$5,200

3 Bedroom, 2.5 Bath Condo for Rent

Available Now

429 W Grant Pl, Unit A

429 W Grant Pl
ChicagoIL60614
property at 4727 N Winchester Ave

$5,250 - $6,630

Total Monthly Price

Total Monthly Price

Base Rent
$5,250 - $6,630
Total Monthly Price
$5,250 - $6,630

3 To 4 Bedroom Condos for Rent

Available Now

4727 N Winchester Ave

ChicagoIL60640
property at 2369 N Lincoln Ave

$5,370

Total Monthly Price

Total Monthly Price

Base Rent
$5,370
Total Monthly Price
$5,370

2 Bedroom, 2 Bath Condo for Rent

Available Now

2369 N Lincoln Ave, Unit 1113

2369 N Lincoln Ave
ChicagoIL60614
property at 1729 W Balmoral Ave

$5,495

Total Monthly Price

Total Monthly Price

Base Rent
$5,495
Total Monthly Price
$5,495

1 Bedroom, 1 Bath Townhome for Rent

Available Now

1729 W Balmoral Ave, Unit Apt 1

1729 W Balmoral Ave
ChicagoIL60640
property at 106 N Aberdeen St

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500
Total Monthly Price
$5,500

1 Bedroom, 1.5 Bath Condo for Rent

Available Now

106 N Aberdeen St, Unit 5

106 N Aberdeen St
ChicagoIL60607
property at 2629 N Dayton St

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500
Total Monthly Price
$5,500

3 Bedroom, 3 Bath Condo for Rent

Available Now

2629 N Dayton St, Unit 3S

2629 N Dayton St
ChicagoIL60614
Showing Results 2001-2050, Page 41 of 52

Chicago, IL Area Reviews

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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 24153 Apartments for Rent in Chicago, IL with pricing that ranges from $500 to $48,409. There are also 5569 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chicago ranging from $400 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 $400 to $58,000 with an average monthly rent of $4,508.

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 $883 to $38,481, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,110 to $40,000. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $850.

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 A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago article

A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago

Written by: Nicole Harms

I’m Nicole, your ApartmentHomeLiving.com Local Expert for Chicago, IL. As a resident of the Chicago area for over 20 years, I’ve learned which neighborhoods are great and which are best avoided.

decorative image for Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago article

Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago

Written by: Nicole Harms

With world-class museums lining its streets, Chicago is a place people go to learn. It’s not surprising, therefore, that it’s also home to multiple colleges and universities with national and global reputations.

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Best Neighborhoods to Rent in Near Chicago's Top Employers

Written by: Nicole Harms

Whenever life takes me into the city, I’m always impressed with the sheer amount of industry and commerce that it holds. With all of that commerce comes a wide range of employment options.

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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 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.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.