Homes for Rent in Chicago, IL Under $2,000 (1,856 Rentals) Page 20 of 38

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property at 2842 N Orchard St
$1,595 - $1,695

Total Monthly Price

Base Rent$1,595 - $1,695
Total Monthly Price$1,595 - $1,695
Studio, 1 Bath Condo for Rent
Available Now
Affordability

2842 N Orchard St

ChicagoIL60657
property at 4410 N Wolcott Ave
$1,595 - $2,195

Total Monthly Price

Base Rent$1,595 - $2,195
Total Monthly Price$1,595 - $2,195
Studio To 1 Bedroom Condos for Rent
Available Now
Affordability

4410 N Wolcott Ave

ChicagoIL60640
property at 1325 N Dearborn St
$1,575 - $1,795

Total Monthly Price

Base Rent$1,575 - $1,795
Total Monthly Price$1,575 - $1,795
Studio, 1 Bath Condo for Rent
Available Now
Affordability

1325 N Dearborn St

ChicagoIL60610
Showing Results 951-1000, Page 20 of 38

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 23812 Apartments for Rent in Chicago, IL with pricing that ranges from $600 to $43,181. There are also 5244 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chicago ranging from $400 to $40,000.

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 $40,000 with an average monthly rent of $2,728.

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 $1,300 to $40,000. Four Bedroom Single-Family rentals are also available starting from $1,080 and Four Bedroom Apartments start at $1,080.

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 How Commercial-to-Residential Property Conversions Help the Housing Crisis article

How Commercial-to-Residential Property Conversions Help the Housing Crisis

Written by: Robin Stewart

Many housing markets throughout America share a common complaint: a lack of affordable rental properties.

decorative image for Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My! article

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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.