Cheap Homes for Rent in Woodlawn Neighborhood of Chicago, IL from $600 (23 Rentals)

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Search the lowest-cost Homes available for rent right now in the Woodlawn area of Chicago.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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

Learn about the best things about living in Chicago from a local in the Insiders Guide to Renting in Chicago. Find your perfect Chicago apartment today!

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Showing Results 1-23, Page 1 of 1

Woodlawn, Chicago, IL Local Guide

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 $699. Oglesby Towers Apartments has the second lowest priced unit, which is a Studio apartment currently listed from $1,076. Here are the most affordable Woodlawn apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
5748 Blackstone By 3L LivingNo Kitchenette with Shared BathroomStudio,1BA$699
Oglesby Towers ApartmentsStudio Floor Plan S1Studio,1BA$1,076
Academy at Drexel1 Bedroom 1 Bath1BR,1BA$1,320
Cloistersclo-1b1a1BR,1BA$2,175
5715-5725 S. Kimbark Avenue5715-2bB2BR,1BA$2,270

Best Value Apartments for Rent in Woodlawn, IL

As of November 17, 2025 the best value apartment in the Woodlawn area is the $2.17 price per square foot 1358-4bA Model at 1358 E. 58th Street in the in the Hyde Park neighborhood starting from $4,395. The second greatest value Woodlawn apartment is the 4 Bed/2 Bath Model at Greenwood Apartments starting at $2,495 with a $1.51 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 ListingModel NameBed/BathPrice Per Sq.Ft.
1358 E. 58th Street1358-4bA4BR,2BA$2.17
Greenwood Apartments4 Bed/2 Bath4BR,2BA$1.51
6530 S Maryland Ave, Unit 26530 S Maryland Ave3BR,2BA$1.53
Cloistersclo-3b3b3BR,3BA$2.32
6217 S Kimbark Ave, Unit GN6217 S Kimbark Ave3BR,2BA$1.60
5715-5725 S. Kimbark Avenue5715-3bB3BR,1BA$2.41
1140 E Marquette Rd, Unit 2D1140 E Marquette Rd2BR,2BA$1.71
6441 S Kenwood Ave, Unit 266441 S Kenwood Ave2BR,1BA$1.69
6619 S Drexel Ave, Unit 16619 S Drexel Ave2BR,2BA$1.78
Academy at Drexel1 Bedroom 1 Bath1BR,1BA$2.21

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

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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A 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

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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Pet Friendly Lifestyle
Woodlawn, Chicago, IL

Ranked #62

Among cities in Illinois for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

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Best Local Schools in
Woodlawn, Chicago, IL

School data provided by Great Schools

Frequently Asked Questions about Woodlawn

What type of rentals are currently available in Woodlawn?

There are currently 276 Apartments for Rent in Woodlawn, IL with pricing that ranges from $699 to $5,995. There are also 72 Single Family Homes for rent, Condos, and Townhome rentals currently available in Woodlawn ranging from $675 to $5,600.

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 $675 to $5,600 with an average monthly rent of $2,461.

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 $1,400 to $3,665, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,800 to $3,200. Four Bedroom Single-Family rentals are also available starting from $1,850 and Four Bedroom Apartments start at $1,800.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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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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.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.