24 N Pulaski Rd
ChicagoIL60624
Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $1,000 (7 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
209 N Kolmar Ave
ChicagoIL60624
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$1,2002 Bedroom Apartments Available Now
5111 W Ferdinand St, Unit 2C
5111 W Ferdinand StChicago, IL 60644
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
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$1,2001 Bedroom Apartments Available Now
4616 W Jackson Blvd, Unit 4616 w Jackson Garden
4616 W Jackson BlvdChicago, IL 60644
320 N Pine Ave, Unit 403
320 N Pine Ave
ChicagoIL60644
346 N Laramie Ave, Unit 2W
346 N Laramie Ave
ChicagoIL60644
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.
5145 W Ferdinand St
ChicagoIL60644
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Madison Square, Chicago, IL Local Guide
How much does it cost to rent a home in Madison Square?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Madison Square 2 Bedroom Homes for Rent | $1,622 | $1,495 | $1,900 |
| Madison Square 3 Bedroom Homes for Rent | $1,920 | $1,150 | $2,700 |
| Madison Square 4 Bedroom Homes for Rent | $2,123 | $1,595 | $3,000 |
| Madison Square 5 Bedroom Homes for Rent | $2,000 | $2,000 | $2,000 |
Browse Homes for Rent in this Neighborhood
There are currently 7 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
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Madison Square, Chicago, IL Local Guide
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Cheapest Available Madison Square Apartments for Rent
The cheapest available apartment rental in the Madison Square area of Chicago, IL is a Studio unit found at 542 N Pine Ave priced from $815. Washington Plaza has the second lowest priced unit, which is a Studio apartment currently listed from $890. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 542 N Pine Ave | 0BR/1.0BA | Studio,1BA | $815 |
| Washington Plaza | Studio Apartment | Studio,1BA | $890 |
| 5125 W Madison | Studio Apartment | Studio,1BA | $895 |
Best Value Apartments for Rent in Madison Square, IL
As of June 11, 2026 the best value apartment in the Madison Square area is the $1.35 price per square foot 5100 W Fulton St Model at 5100 W Fulton St, Unit 1 in the in the Austin neighborhood starting from $3,500. The second greatest value Madison Square apartment is the 328 N Lockwood Ave Model at 328 N Lockwood Ave, Unit 2 starting at $2,340 with a $0.98 price per square foot in the Austin neighborhood. Here is today’s list of the best values for Madison Square apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 5100 W Fulton St, Unit 1 | 5100 W Fulton St | 4BR,2BA | $1.35 |
| 328 N Lockwood Ave, Unit 2 | 328 N Lockwood Ave | 3BR,1BA | $0.98 |
| 217 N Laramie Ave, Unit 1 | 217 N Laramie Ave | 5BR,2BA | $1.08 |
| 5078 W Adams St, Unit 1 | 5078 W Adams St | 3BR,1BA | $1.33 |
| 4306 W Maypole Ave, Unit 1F | 4306 W Maypole Ave | 4BR,1BA | $1.45 |
| 200 N Kenneth Ave | 2/1.0 | 2BR,1BA | $1.30 |
| 109 N Laramie Ave | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.52 |
| Austin Apartments | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.55 |
| Congress Commons | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.68 |
| 542 N Pine Ave | 0BR/1.0BA | Studio ,1BA | $1.52 |
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.
Read Article
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.
Read ArticleQuick 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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If you’re an expert on all things Madison Square, tell us what you love (and don't) by rating it and writing a review.
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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #92
Among cities in Illinois for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about Madison Square
What type of rentals are currently available in Madison Square?
There are currently 302 Apartments for Rent in Madison Square, IL with pricing that ranges from $890 to $3,500. There are also 29 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $1,000 to $3,000.
What is the current price range for Rental Homes in Madison Square?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Madison Square ranges from $1,000 to $3,000 with an average monthly rent of $1,755.
How much are larger Three and Four Bedroom Rentals in Madison Square?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Madison Square range from $1,700 to $2,400, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,150 to $2,700. Four Bedroom Single-Family rentals are also available starting from $1,595 and Four Bedroom Apartments start at $1,740.
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
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.
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.
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.
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
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.
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.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.