
Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $900 (2 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.


5315 W Van Buren St
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
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 | $1,200 | $1,800 |
Madison Square 3 Bedroom Homes for Rent | $1,942 | $1,450 | $2,800 |
Browse Homes for Rent in this Neighborhood
There are currently 2 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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Best Value Apartments for Rent in Madison Square, IL
As of March 28, 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 4 Bedroom 2 Bathroom Apartment Model at 5556-64 W Jackson Blvd starting at $1,610 with a $1.26 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 | $0.87 |
5556-64 W Jackson Blvd | 4 Bedroom 2 Bathroom Apartment | 4BR,2BA | $1.26 |
4118 W Van Buren St, Unit 2 | 4118 W Van Buren St | 3BR,1BA | $1.60 |
4814 W Monroe | 3 Bedroom 1 Bathroom Apartment | 3BR,1BA | $1.30 |
5100-04 W Madison St | 2 Bedroom 1.5 Bath Apartments | 2BR,1.5BA | $1.43 |
415-425 S. Taylor Ave. | 417A S. Taylor B | 1BR,1BA | $2.02 |
618-632 S. Austin Blvd. | 618 S. Austin B, 624 S. Austin G, 626 S. Austin... | 1BR,1BA | $2.30 |
330 N Pine | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $2.04 |
5125 W Madison St | Studio Apartment | Studio ,1BA | $1.98 |
Washington Plaza | Studio Apartment | Studio ,1BA | $2.26 |
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Frequently Asked Questions about Madison Square
What type of rentals are currently available in Madison Square?
There are currently 301 Apartments for Rent in Madison Square, IL with pricing that ranges from $795 to $2,549. There are also 12 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $900 to $2,800.
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 $900 to $2,800 with an average monthly rent of $1,447.
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.

Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.