4728 W Madison St
ChicagoIL60644
Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $900 (6 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
1200 S Kedvale Ave
ChicagoIL60624
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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.
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4058 W Congress Pkwy
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 | $1,610 | $1,400 | $1,850 |
| Madison Square 3 Bedroom Homes for Rent | $1,710 | $1,500 | $2,400 |
| Madison Square 4 Bedroom Homes for Rent | $2,025 | $1,850 | $2,200 |
Browse Homes for Rent in this Neighborhood
There are currently 6 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 Washington Plaza priced from $850. 4114 W Washington Blvd has the second lowest priced unit, which is a Studio apartment currently listed from $865. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Washington Plaza | Studio Apartment | Studio,1BA | $850 |
| 4114 W Washington Blvd | Studio Apartment | Studio,1BA | $865 |
| Pine North | 1BR/1.0BA | 1BR,1BA | $975 |
Best Value Apartments for Rent in Madison Square, IL
As of September 16, 2025 the best value apartment in the Madison Square area is the $1.40 price per square foot 5078 W Adams St Model at 5078 W Adams St, Unit 2 in the in the Austin neighborhood starting from $1,900. 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. |
|---|---|---|---|
| 5078 W Adams St, Unit 2 | 5078 W Adams St | 3BR,1BA | $1.40 |
| 4238 W Grenshaw St, Unit g | 4238 W Grenshaw St | 3BR,1BA | $1.33 |
| 5100-04 W Madison St | 3 Bedroom 2 Bathroom Apartment | 3BR,2BA | $1.18 |
| 4015 W Wilcox St, Unit 2 | 4015 W Wilcox St | 3BR,2BA | $1.50 |
| 4814 W Monroe | 2 Bedroom 1 Bathroom Garden Apartment | 2BR,1BA | $1.54 |
| 5328 W Harrison | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.48 |
| 4641-43 W Jackson Blvd | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.67 |
| 5236 W Harrison | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.67 |
| Pine North | 1BR/1.0BA | 1BR,1BA | $1.52 |
| 418-24 S Laramie Ave | 1 Bedroom 1 Bathroom Apartment | 1BR,1BA | $1.73 |
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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #107
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 294 Apartments for Rent in Madison Square, IL with pricing that ranges from $850 to $1,900. There are also 19 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $950 to $2,400.
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 $950 to $2,400 with an average monthly rent of $1,469.
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.
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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.