Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (10 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.

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123 N Central Ave
Studio to 1 Bedroom Apartments

123 N Central Ave

123 N Central AveChicago, IL 60644
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5125 W Madison St
Studio to 1 Bedroom Apartments

5125 W Madison St

5125 W Madison StChicago, IL 60644
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Pine North
1 Bedroom Apartments

Pine North

542 N Pine AveChicago, IL 60644
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729 N Central
1 Bedroom Apartments

729 N Central

729 N Central AveChicago, IL 60644

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

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 $825. 5125 W Madison St has the second lowest priced unit, which is a Studio apartment currently listed from $875. Here are the most affordable Madison Square apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
Washington PlazaStudio ApartmentStudio,1BA$825
5125 W Madison StStudio ApartmentStudio,1BA$875
Pine North1BR/1.0BA1BR,1BA$950

Best Value Apartments for Rent in Madison Square, IL

As of February 14, 2025 the best value apartment in the Madison Square area is the $1.42 price per square foot 711 S Tripp Ave Model at 711 S Tripp Ave, Unit 2 in the in the Lawndale neighborhood starting from $1,700. The second greatest value Madison Square apartment is the 2BR/1.0BA Model at 200 N Kenneth starting at $1,275 with a $1.28 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 ListingModel NameBed/BathPrice Per Sq.Ft.
711 S Tripp Ave, Unit 2711 S Tripp Ave3BR,1BA$1.42
200 N Kenneth2BR/1.0BA2BR,1BA$1.28
418-24 S Laramie Ave3 Bedroom 1 Bathroom Apartment3BR,1BA$1.49
551 N Lavergne Ave, Unit 551 2ND FLR551 N Lavergne Ave2BR,1BA$1.37
634-640 N Lamon2BR/1.0BA2BR,1BA$1.56
101-111 S. Harvey Ave. and 237-249 South Blvd101 S. Harvey W, 103 S. Harvey, 239 South W, 24...1BR,1BA$1.85
511-521 S. Cuyler Ave.511 S. Cuyler N & 521 S. Cuyler S1BR,1BA$1.91
1115 S Karlov Ave2 Bedroom 1 Bath Apartment2BR,1BA$1.55
Pine North1BR/1.0BA1BR,1BA$1.60
729 N Central1 Bedroom 1 Bath Apartment1BR,1BA$1.83

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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 Washington Plaza listed at $825.

How much is rent for a Cheap One Bedroom Madison Square Apartment?

The lowest price for a Cheap One Bedroom Madison Square Apartment is $950 at Pine North.

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 $1,085 at 1115 S Karlov Ave.

What is the most affordable Madison Square Three Bedroom Apartment?

The best deal on a cheap Madison Square Three Bedroom Apartment rental is at 418-24 S Laramie Ave and starts from $1,420.

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.

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