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$1,0501 Bedroom Apartments Available Now
10 N Long Ave
10 N Long AveChicago, IL 60644
Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $1,100 (9 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
209 N Kolmar Ave
ChicagoIL60624
5459 W Chicago Ave
ChicagoIL60651
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$1,2001 Bedroom Apartments Available Now
5446 W Huron St
5446 W Huron StChicago, IL 60644
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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$1,2502 Bedroom Apartments Available Now
4622 W Jackson Blvd
4622 W Jackson BlvdChicago, IL 60644
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$1,3003 Bedroom Apartments Available Now
4834 W Adams St
4834 W Adams StChicago, IL 60644
5257 W Lexington St
ChicagoIL60644
5257 W Lexington St
ChicagoIL60644
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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$1,3002 Bedroom Apartments Available Now
4538 W Jackson Blvd
4538 W Jackson BlvdChicago, IL 60624
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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 | $1,333 | $1,300 | $1,400 |
| Madison Square 3 Bedroom Homes for Rent | $1,675 | $1,150 | $2,200 |
| Madison Square 4 Bedroom Homes for Rent | $2,200 | $1,800 | $2,600 |
| Madison Square 5 Bedroom Homes for Rent | $6,400 | $6,400 | $6,400 |
Browse Homes for Rent in this Neighborhood
There are currently 9 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 Pine North priced from $775. 4114 W Washington Blvd Chicago, IL 60624 has the second lowest priced unit, which is a Studio apartment currently listed from $825. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Pine North | 0BR/1.0BA | Studio,1BA | $775 |
| 4114 W Washington Blvd Chicago, IL 60624 | Studio Apartment | Studio,1BA | $825 |
| 5501 W Washington Blvd Chicago, IL 60644 | Studio Apartment | Studio,1BA | $890 |
Best Value Apartments for Rent in Madison Square, IL
As of January 10, 2026 the best value apartment in the Madison Square area is the $1.23 price per square foot 4644 W Gladys Ave Model at 4644 W Gladys Ave, Unit 1 in the in the West Garfield Park neighborhood starting from $1,600. The second greatest value Madison Square apartment is the 4238 W Grenshaw St Model at 4238 W Grenshaw St, Unit g starting at $1,600 with a $1.33 price per square foot in the Lawndale 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. |
|---|---|---|---|
| 4644 W Gladys Ave, Unit 1 | 4644 W Gladys Ave | 3BR,1BA | $1.23 |
| 4238 W Grenshaw St, Unit g | 4238 W Grenshaw St | 3BR,1BA | $1.33 |
| 5223-5225 W Washington Blvd | 3 Bed 1 Bath | 3BR,1BA | $1.55 |
| 148 N La Crosse Ave Chicago, IL 60644 | 3 Bedroom 1 Bath Apartment | 3BR,1BA | $1.18 |
| 200 N Kenneth | 2/1.0 | 2BR,1BA | $1.35 |
| 238 N Lockwood Ave | 238 N Lockwood Ave | 3BR,1BA | $1.50 |
| 4814-4820 W Monroe St Chicago, IL 60644 | 2 Bedroom 1 Bath Garden | 2BR,1BA | $1.36 |
| 5448 W Adams St 119-21 N Lotus Chicago, IL 60644 | 3 Bedroom 1 Bath Apartment | 3BR,1BA | $1.42 |
| 634-640 N Lamon | 2/1.0 | 2BR,1BA | $1.56 |
| 723-25 N Central Ave Chicago, IL 60644 | 2 Bedroom 2 Bath Apartment | 2BR,2BA | $1.57 |
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 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
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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 #115
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 303 Apartments for Rent in Madison Square, IL with pricing that ranges from $825 to $10,863. There are also 23 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $1,150 to $6,400.
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 $6,400 with an average monthly rent of $2,443.
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
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!