6550 S Drexel Ave
ChicagoIL60637
Cheap Homes for Rent in the Woodlawn Neighborhood of Chicago, IL from $1,250 (13 Rentals)
Search the lowest-cost Homes available for rent right now in the Woodlawn area of Chicago.
6529 S Kimbark Ave
ChicagoIL60637
6529 S Kimbark Ave, Unit 2R
6529 S Kimbark Ave
ChicagoIL60637
5800 S Blackstone Ave
ChicagoIL60637
6525 S Evans Ave
ChicagoIL60637
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$1,3752 Bedroom Apartments Available Now
6525 S Evans Ave, Unit 1
6525 S Evans AveChicago, IL 60637
The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Chicago may cost more than the national average, but with the right neighborhood, a smart transit strategy, and a few local insider tips, living well in the Windy City is more achievable than you might think. Our local expert breaks down everything from rent and groceries to transportation and healthcare so you can plan your move with confidence.
6634 S Greenwood Ave
ChicagoIL60637
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$1,4502 Bedroom Apartments Available Now
6525 S Evans Ave, Unit 1
6525 S Evans AveChicago, IL 60637
6225 S Dorchester Ave
ChicagoIL60637
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$1,5002 Bedroom Apartments Available Now
853 E 64th St
853 E 64th StChicago, IL 60637
6700 S Paxton Ave
ChicagoIL60649
6714 S Chappel Ave
ChicagoIL60649
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
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$1,6002 Bedroom Apartments Available Now
6656 S Woodlawn Ave, Unit 3
6656 S Woodlawn AveChicago, IL 60637
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Woodlawn, Chicago, IL Local Guide
Copyright CoStar Group, Inc
How much does it cost to rent a home in Woodlawn?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Woodlawn 2 Bedroom Homes for Rent | $1,708 | $1,250 | $2,600 |
| Woodlawn 3 Bedroom Homes for Rent | $2,356 | $1,700 | $3,300 |
| Woodlawn 4 Bedroom Homes for Rent | $3,233 | $2,500 | $3,600 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 13 rentals with your search options within a 2 mile radius of the Woodlawn Neighborhood of Chicago, IL.
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Woodlawn, Chicago, IL Local Guide
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Cheapest Available Woodlawn Apartments for Rent
The cheapest available apartment rental in the Woodlawn area of Chicago, IL is a Studio unit found at 5748 Blackstone By 3L Living priced from $726. Jeffery Parkway Apartments has the second lowest priced unit, which is a Studio apartment currently listed from $925. Here are the most affordable Woodlawn apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 5748 Blackstone By 3L Living | No Kitchenette with Shared Bathroom | Studio,1BA | $726 |
| Jeffery Parkway Apartments | Studio | Studio,1BA | $925 |
| Plaisance Apartments | Studio Floor Plan S1 | Studio,1BA | $1,122 |
| Academy at Drexel | 2 Bedroom 1 Bath Plan B | 2BR,1BA | $1,575 |
| 6700-12 S Chappel | STUNNING + SPACIOUS 2 Bedroom apartment in quie... | 2BR,1BA | $1,650 |
Best Value Apartments for Rent in Woodlawn, IL
As of August 30, 2026 the best value apartment in the Woodlawn area is the $2.41 price per square foot 1358-4b Model at 1358 E. 58th Street in the in the Hyde Park neighborhood starting from $4,895. The second greatest value Woodlawn apartment is the 4 Bed/3 Bath Model at Greenwood Apartments starting at $2,980 with a $1.70 price per square foot in the Woodlawn neighborhood. Here is today’s list of the best values for Woodlawn apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 1358 E. 58th Street | 1358-4b | 4BR,2BA | $2.41 |
| Greenwood Apartments | 4 Bed/3 Bath | 4BR,3BA | $1.70 |
| 843 E Marquette Rd, Unit 2 | 843 E Marquette Rd | 4BR,1BA | $1.67 |
| 1140 E Marquette Rd | 1140 E Marquette Rd | 3BR,2BA | $1.73 |
| 5756 S Kenwood Ave, Unit A | 5756 S Kenwood Ave | 3BR,2BA | $2.19 |
| Cloisters | clo-2b1c | 2BR,1BA | $2.56 |
| Oglesby Towers Apartments | 2 Bedrooms Floor Plan B1B | 2BR,2BA | $1.43 |
| Academy at Drexel | 2 Bedroom 1 Bath Plan B | 2BR,1BA | $1.73 |
| Jeffery Parkway Apartments | Studio | Studio ,1BA | $2.31 |
| 5748 Blackstone By 3L Living | Shared Kitchenette & Bathroom | Studio ,1BA | $2.66 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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Best Neighborhoods to Rent in Near Chicago's Top Employers: A Guide for Renters
A Local Expert's Guide to The 10 Best Chicago Neighborhoods near Major Local Employers. Find your perfect Chicago, IL apartment, condo, or rental home today at ApartmentHomeLiving.com
Read ArticleA Local Expert's Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago
A Local Expert's guide to the Best Student Friendly Neighborhoods Near Colleges in the Chicago, IL metro area for affordable living. Find your perfect Chicago Student apartment, condo, or rental home today at ApartmentHomeliving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Best Local Schools in Woodlawn, Chicago, IL
Carnegie Elementary School
City Of Chicago School District 299
Public School - Grades K-8 (389)
5 out of 10
Hyde Park Academy High School
City Of Chicago School District 299
Public School - Grades 9-12 (757)
2 out of 10
Wadsworth PreK-8th STEM School
City Of Chicago School District 299
Public School - Grades PK-8 (484)
4 out of 10
School data provided by Great Schools
Frequently Asked Questions about Woodlawn
What type of rentals are currently available in Woodlawn?
There are currently 273 Apartments for Rent in Woodlawn, IL with pricing that ranges from $726 to $3,599. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Woodlawn ranging from $1,250 to $3,600.
What is the current price range for Rental Homes in Woodlawn?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Woodlawn ranges from $1,250 to $3,600 with an average monthly rent of $2,199.
How much are larger Three and Four Bedroom Rentals in Woodlawn?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Woodlawn range from $1,665 to $3,599, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,700 to $3,300. Four Bedroom Single-Family rentals are also available starting from $2,500 and Four Bedroom Apartments start at $1,625.
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.
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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.
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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.