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$1,0501 Bedroom Apartments Available Now
14 N Long Ave, Unit G
14 N Long AveChicago, IL 60644
Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $1,100 (8 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
209 N Kolmar Ave
ChicagoIL60624
320 N Pine Ave, Unit 403
320 N Pine Ave
ChicagoIL60644
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$1,3503 Bedroom Apartments Available Now
4622 W Jackson Blvd, Unit 2
4622 W Jackson BlvdChicago, 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.
4033 W Gladys Ave
ChicagoIL60624
4035 W Gladys Ave, Unit N3
4035 W Gladys Ave
ChicagoIL60624
646 N Long Ave
ChicagoIL60644
4058 W Congress Pkwy, Unit 2S
4058 W Congress Pkwy
ChicagoIL60624
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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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 | $1,460 | $1,400 | $1,600 |
| Madison Square 3 Bedroom Homes for Rent | $1,793 | $1,150 | $2,500 |
| Madison Square 4 Bedroom Homes for Rent | $1,672 | $1,595 | $1,750 |
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 8 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
- Nearby Chicago neighborhoods
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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 4114 W Washington Blvd Chicago, IL 60624 priced from $875. 5501 W Washington Blvd Chicago, IL 60644 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 |
|---|---|---|---|
| 4114 W Washington Blvd Chicago, IL 60624 | Studio Apartment | Studio,1BA | $875 |
| 5501 W Washington Blvd Chicago, IL 60644 | Studio Apartment | Studio,1BA | $890 |
| 5125 W Madison St Chicago, IL 60644 | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,080 |
Best Value Apartments for Rent in Madison Square, IL
As of April 25, 2026 the best value apartment in the Madison Square area is the $0.66 price per square foot 2Bd/1B - w/ an office Model at 5567 W Van Buren St in the in the Austin neighborhood starting from $1,900. The second greatest value Madison Square apartment is the 3 Bedroom 1 Bath Garden Model at 4653-59 W Jackson Blvd Chicago, IL 60644 starting at $1,830 with a $1.32 price per square foot in the West Garfield Park 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. |
|---|---|---|---|
| 5567 W Van Buren St | 2Bd/1B - w/ an office | 2BR,1BA | $0.66 |
| 4653-59 W Jackson Blvd Chicago, IL 60644 | 3 Bedroom 1 Bath Garden | 3BR,1BA | $1.32 |
| 5078 W Adams St, Unit 1 | 5078 W Adams St | 3BR,1BA | $1.33 |
| 208 N Kolin Ave, Unit 3 | 208 N Kolin Ave | 3BR,1BA | $1.38 |
| 208 N Kolin Ave, Unit 3 | 208 N Kolin Ave | 3BR,1BA | $1.50 |
| 5017 W Huron St, Unit 2 | 5017 W Huron St | 3BR,1BA | $1.62 |
| 200 N Kenneth | 2/1.0 | 2BR,1BA | $1.35 |
| 400-08 S Laramie Ave Chicago, IL 60644 | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.33 |
| 5125 W Madison St Chicago, IL 60644 | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.61 |
| 5018 W Jackson Blvd Chicago, IL 60644 | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.73 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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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 ArticleBest 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 ArticleThe 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.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
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 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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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #88
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 304 Apartments for Rent in Madison Square, IL with pricing that ranges from $875 to $10,656. There are also 23 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $1,150 to $2,500.
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 $1,150 to $2,500 with an average monthly rent of $1,556.
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 $1,350 to $2,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,150 to $2,500. Four Bedroom Single-Family rentals are also available starting from $1,595 and Four Bedroom Apartments start at $1,800.
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
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.