Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $600 (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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Garfield Apartments
Studio Apartments

Garfield Apartments

4342 W Washington BlvdChicago, IL 60624
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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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La Rose Apartments
1 to 2 Bedroom Apartments

La Rose Apartments

5501 W Monroe StChicago, IL 60644
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330 N Pine
1 Bedroom Apartments

330 N Pine

330 N Pine AveChicago, IL 60644
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5314 W Washington Blvd
1 Bedroom Apartments

5314 W Washington Blvd

5314 W Washington BlvdChicago, IL 60644
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5100-04 W Madison St
2 to 3 Bedroom Apartments

5100-04 W Madison St

5100-5104 W Madison StChicago, IL 60644
  • Utilities Included

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 5125 W Madison St priced from $660. 4114 W Washington Blvd has the second lowest priced unit, which is a Studio apartment currently listed from $795. Here are the most affordable Madison Square apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
5125 W Madison StStudio ApartmentStudio,1BA$660
4114 W Washington BlvdStudio ApartmentStudio,1BA$795
Washington PlazaStudio ApartmentStudio,1BA$830

Best Value Apartments for Rent in Madison Square, IL

As of March 29, 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 ListingModel NameBed/BathPrice Per Sq.Ft.
5100 W Fulton St, Unit 15100 W Fulton St4BR,2BA$0.87
5556-64 W Jackson Blvd4 Bedroom 2 Bathroom Apartment4BR,2BA$1.26
4118 W Van Buren St, Unit 24118 W Van Buren St3BR,1BA$1.60
5735 W. Washington Blvd3BR/1.0BA3BR,1BA$2.50
5100-04 W Madison St2 Bedroom 1.5 Bath Apartments2BR,1.5BA$1.43
415-425 S. Taylor Ave.417A S. Taylor B1BR,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 Pine1 Bedroom 1 Bath Apartment1BR,1BA$2.04
5125 W Madison StStudio ApartmentStudio ,1BA$1.50
Washington PlazaStudio ApartmentStudio ,1BA$2.36

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Pet Friendly Lifestyle
Madison Square, Chicago, IL

Ranked #88

Among neighborhoods in Chicago, IL for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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Frequently Asked Questions about Cheap Madison Square Apartments

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

The lowest price for a Cheap One Bedroom Madison Square Apartment is $1,035 at Washington Plaza.

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 5100-04 W Madison St.

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 $1,095.

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.

decorative image for A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago article

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.

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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.

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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.

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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.