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from $820Studio to 1 Bedroom Apartments Available Now
4114 W Washington Blvd
4114 W Washington BlvdChicago, IL 60624
Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (10 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
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from $845Studio to 2 Bedroom Apartments Available Now
Washington Plaza
5501 W Washington BlvdChicago, IL 60644
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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.
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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
Showing Results 1-10, Page 1 of 1
Madison Square, Chicago, IL Local Guide
How much does it cost to rent an apartment in Madison Square?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Madison Square Studio Apartments | $856 | $845 | $865 |
| Madison Square 1 Bedroom Apartments | $1,322 | $1,199 | $1,509 |
| Madison Square 2 Bedroom Apartments | $1,543 | $1,200 | $1,860 |
| Madison Square 3 Bedroom Apartments | $2,121 | $1,700 | $2,549 |
| Madison Square 4 Bedroom Apartments | $2,050 | $1,850 | $2,250 |
Browse Apartments in this Neighborhood
There are currently 10 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 | $845 |
Best Value Apartments for Rent in Madison Square, IL
As of April 27, 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 $2,549 with a $1.70 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 | $1.70 |
| 5100-04 W Madison St | 3 Bedroom 2 Bathroom Apartment | 3BR,2BA | $1.12 |
| 4815 W Monroe St | 3 Bedrooms | 3BR,2BA | $1.50 |
| 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 |
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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #88
Among neighborhoods in Chicago, IL for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about Cheap Madison Square Apartments
What is the Cheapest Studio apartment in Madison Square?
Currently the most affordable Cheap Studio Apartment in Madison Square is at 701 S Karlov Ave listed at $815.
What is the lowest price for a Cheap Two Bedroom Madison Square Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Madison Square is starting from $1,180 at 4641-43 W Jackson Blvd.
What is the most affordable Madison Square Three Bedroom Apartment?
The best deal on a cheap Madison Square Three Bedroom Apartment rental is at 5100-04 W Madison St and starts from $1,290.
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.