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Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $1,300 (8 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
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4838 W Fulton St
ChicagoIL60644
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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.
4058 W Congress Pkwy
ChicagoIL60624
4017 W Van Buren St
ChicagoIL60624
4133 W Carroll Ave
ChicagoIL60624
4052 W Arthington St
ChicagoIL60624
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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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 | $1,500 | $1,350 | $1,800 |
| Madison Square 3 Bedroom Homes for Rent | $1,740 | $1,450 | $2,350 |
| Madison Square 4 Bedroom Homes for Rent | $1,850 | $1,850 | $1,850 |
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
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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 has the second lowest priced unit, which is a Studio apartment currently listed from $800. 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 | Studio Apartment | Studio,1BA | $800 |
| Washington Plaza | Studio Apartment | Studio,1BA | $860 |
Best Value Apartments for Rent in Madison Square, IL
As of November 07, 2025 the best value apartment in the Madison Square area is the $1.18 price per square foot 162 N La Crosse Ave Model at 162 N La Crosse Ave, Unit 2nd Fl. in the in the Austin neighborhood starting from $1,650. The second greatest value Madison Square apartment is the 4644 W Gladys Ave Model at 4644 W Gladys Ave, Unit 1 starting at $1,700 with a $1.31 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. |
|---|---|---|---|
| 162 N La Crosse Ave, Unit 2nd Fl. | 162 N La Crosse Ave | 2BR,1BA | $1.18 |
| 4644 W Gladys Ave, Unit 1 | 4644 W Gladys Ave | 3BR,1BA | $1.31 |
| 4238 W Grenshaw St, Unit g | 4238 W Grenshaw St | 3BR,1BA | $1.33 |
| 708-14 S Karlov Ave | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.24 |
| 200 N Kenneth | 2BR/1.0BA | 2BR,1BA | $1.35 |
| 238 N Lockwood Ave | 238 N Lockwood Ave | 3BR,1BA | $1.50 |
| 4203 W Maypole Ave | 4203 W Maypole Ave | 3BR,1BA | $1.65 |
| 5328 W Harrison | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.56 |
| 400-08 S Laramie Ave | 2 Bedroom 1 Bathroom Apartment | 2BR,1BA | $1.65 |
| 4815 W Monroe St | 1 Bedroom | 1BR,1BA | $1.58 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
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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 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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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #126
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 $800 to $11,195. There are also 15 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $1,350 to $2,350.
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 $1,350 to $2,350 with an average monthly rent of $1,696.
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.
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.
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!
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.