417 S Karlov Ave
ChicagoIL60624
Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $1,400 (8 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
4331 W Wilcox St
ChicagoIL60624
646 N Long Ave
ChicagoIL60644
4133 W Carroll Ave
ChicagoIL60624
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.
4052 W Arthington St
ChicagoIL60624
4938 W Monroe St
ChicagoIL60644
4938 W Monroe St
ChicagoIL60644
5233 W Quincy St
ChicagoIL60644
Chicago's Best Affordable Neighborhoods
Learn about Chicago and the best places to live with original content written by our Chicago, IL Local Expert Nicole Harms
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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 | $1,550 | $1,500 | $1,600 |
| Madison Square 3 Bedroom Homes for Rent | $1,725 | $1,450 | $2,200 |
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 701 S Karlov Ave priced from $815. 4114 W Washington Blvd has the second lowest priced unit, which is a Studio apartment currently listed from $820. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 701 S Karlov Ave | Studio Apartment | Studio,1BA | $815 |
| 4114 W Washington Blvd | Studio Apartment | Studio,1BA | $820 |
| Washington Plaza | Studio Apartment | Studio,1BA | $860 |
Best Value Apartments for Rent in Madison Square, IL
As of April 30, 2025 the best value apartment in the Madison Square area is the $0.87 price per square foot 5100 W Fulton St Model at 5100 W Fulton St, Unit 1 in the in the Austin neighborhood starting from $2,250. The second greatest value Madison Square apartment is the 415 S. Taylor A Model at 415-425 S. Taylor Ave. starting at $2,449 with a $1.63 price per square foot in the Oak Park Historic District 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 | $0.87 |
| 415-425 S. Taylor Ave. | 415 S. Taylor A | 3BR,2BA | $1.63 |
| 5100-04 W Madison St | 3 Bedroom 2 Bathroom Apartment | 3BR,2BA | $1.12 |
| 200 N Kenneth | 2BR/1.0BA | 2BR,1BA | $1.45 |
| 418-24 S Laramie Ave | 3 Bedroom 2 Bathroom Apartment | 3BR,2BA | $1.51 |
| 5024 W Quincy St | 3 Bedroom 1 Bath Apartment | 3BR,1BA | $1.60 |
| 4641-43 W Jackson Blvd | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.81 |
| 5011 W Maypole Ave | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.81 |
| 500-14 S Laramie Ave | 1 Bedroom 1 Bathroom Apartment | 1BR,1BA | $1.80 |
| 701 S Karlov Ave | Studio Apartment | Studio ,1BA | $1.86 |
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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 $820 to $2,449. There are also 13 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $1,450 to $2,200.
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 $1,450 to $2,200 with an average monthly rent of $1,637.
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.
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.
Rise of Digital Nomads: Remote Work Tips for Apartment Renters
Written by: Brandie Parton
As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.