Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (8 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
Lifestyle Matching SearchDone
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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

close
View Me
Garfield Apartments
Studio Apartments

Garfield Apartments

4342 W Washington BlvdChicago, IL 60624
  • Utilities Inc.
close
View Me
123 N Central Ave
Studio to 1 Bedroom Apartments

123 N Central Ave

123 N Central AveChicago, IL 60644
  • Utilities Inc.
close
View Me
La Rose Apartments
1 to 2 Bedroom Apartments

La Rose Apartments

5501 W Monroe StChicago, IL 60644
  • Utilities Inc.
close
View Me
Pine North
1 Bedroom Apartments

Pine North

542 N Pine AveChicago, IL 60644
  • Utilities Inc.

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 4114 W Washington Blvd priced from $795. Washington Plaza has the second lowest priced unit, which is a Studio apartment currently listed from $810. Here are the most affordable Madison Square apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
4114 W Washington BlvdStudio ApartmentStudio,1BA$795
Washington PlazaStudio ApartmentStudio,1BA$810
Pine North1BR/1.0BA1BR,1BA$950

Best Value Apartments for Rent in Madison Square, IL

As of March 02, 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 5241 W Washington Blvd Model at 5241 W Washington Blvd, Unit 2nd fl. starting at $1,700 with a $1.06 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
5241 W Washington Blvd, Unit 2nd fl.5241 W Washington Blvd3BR,1BA$1.06
711 S Tripp Ave, Unit 2711 S Tripp Ave3BR,1BA$1.42
4814 W Monroe3 Bedroom 1 Bathroom Apartment3BR,1BA$1.12
200 N Kenneth2BR/1.0BA2BR,1BA$1.25
551 N Lavergne Ave, Unit 551 2ND FLR551 N Lavergne Ave2BR,1BA$1.37
400-08 S Laramie Ave2 Bedroom 1 Bathroom Apartment2BR,1BA$1.54
511-521 S. Cuyler Ave.511 S. Cuyler N & 521 S. Cuyler S1BR,1BA$1.91
238-250 Washington Blvd. and 347-357 S. Harvey Ave.248 Washington A1BR,1BA$1.96
Pine North1BR/1.0BA1BR,1BA$1.60

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle

Ranked #

Pet Friendliness Lifestyle Score

decorative image of woman handing cat to small boy

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 4114 W Washington Blvd listed at $795.

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 $1,165 at 400-08 S Laramie 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 4814 W Monroe and starts from $1,295.

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.

decorative image for Understanding Amenity Fees: Know Where You Might Be Able to Save Money article

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.

decorative image for What to Know About Fees and Fines When Renting article

What to Know About Fees and Fines When Renting

Written by: Trey Huguley

When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.

decorative image for Battling the Butts: Your Guide to the Reality of Smoke-Free Renting article

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.