Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (58 Rentals)

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

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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property at 646 N Long Ave

$1,400

Total Monthly Price

Total Monthly Price

Base Rent
$1,400
Total Monthly Price
$1,400

2 Bedroom, 1 Bath Townhome for Rent

Available Now

646 N Long Ave

ChicagoIL60644
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Garfield Apartments
Studio to 1 Bedroom Apartments

Garfield Apartments

4342 W Washington BlvdChicago, IL 60624
  • Utilities Included
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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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542 N Pine Ave
Studio to 3 Bedroom Apartments

542 N Pine Ave

542 N Pine AveChicago, IL 60644
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La Rose Apartments
1 to 3 Bedroom Apartments

La Rose Apartments

5501 W Monroe StChicago, IL 60644
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Austin Apartments
1 to 4 Bedroom Apartments

Austin Apartments

5101-5103 W Monroe StChicago, IL 60644

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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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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Pangea Apartments
2 to 3 Bedroom Apartments

Pangea Apartments

5448 W Adams StChicago, IL 60644
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4815 W Monroe
1 to 4 Bedroom Apartments

4815 W Monroe

4815 W Monroe StChicago, IL 60644
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Jade Apartments
Studio to 2 Bedroom Apartments

Jade Apartments

1-15 N Keeler AveChicago, IL 60624
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4152-4156 W Lake St
Studio to 6 Bedroom Apartments

4152-4156 W Lake St

4152-4156 W Lake StChicago, IL 60624

Chicago Relocation 101: Mastering Utilities, Registration, and the CTA

Moving to Chicago? This essential relocation guide offers a complete checklist for new residents, covering finding the right neighborhood, setting up utilities (ComEd, People’s Gas), and mastering high-rise moving logistics and vehicle registration.

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4443 W Gladys Ave
2 to 3 Bedroom Apartments

4443 W Gladys Ave

4443 W Gladys AveChicago, IL 60624
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634 N Lamon Ave
2 Bedroom Apartments

634 N Lamon Ave

634 N Lamon AveChicago, IL 60644

Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

Learn about the best things about living in Chicago from a local in the Insiders Guide to Renting in Chicago. Find your perfect Chicago apartment today!

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Showing Results 1-50, Page 1 of 2

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 Chicago, IL 60624 priced from $875. 5501 W Washington Blvd Chicago, IL 60644 has the second lowest priced unit, which is a Studio apartment currently listed from $890. Here are the most affordable Madison Square apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
4114 W Washington Blvd Chicago, IL 60624Studio ApartmentStudio,1BA$875
5501 W Washington Blvd Chicago, IL 60644Studio ApartmentStudio,1BA$890
5125 W Madison St Chicago, IL 606441 Bedroom 1 Bath Apartment1BR,1BA$1,080
418-24 S Laramie Ave Chicago, IL 606441 Bedroom 1 Bath Apartment with Dining1BR,1BA$1,120
5018 W Jackson Blvd Chicago, IL 606441 Bedroom 1 Bath Apartment1BR,1BA$1,125
330 N Pine Ave Chicago, IL 606441 Bedroom 1 Bath Apartment1BR,1BA$1,125
5500 W Van Buren St Chicago, IL 606442 Bedroom 1 Bath Apartment2BR,1BA$1,155
400-402 S Kilbourn Ave Chicago, IL 606242 Bedroom 1 Bath Apartment2BR,1BA$1,170
400-08 S Laramie Ave Chicago, IL 606442 Bedroom 1 Bath Apartment2BR,1BA$1,265
729 N Central Chicago, IL 606442 Bedroom 1 Bath Garden2BR,1BA$1,270

Best Value Apartments for Rent in Madison Square, IL

As of April 26, 2026 the best value apartment in the Madison Square area is the $0.66 price per square foot 2Bd/1B - w/ an office Model at 5567 W Van Buren St in the in the Austin neighborhood starting from $1,900. The second greatest value Madison Square apartment is the 3 Bedroom 1 Bath Garden Model at 4653-59 W Jackson Blvd Chicago, IL 60644 starting at $1,830 with a $1.32 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.
5567 W Van Buren St2Bd/1B - w/ an office2BR,1BA$0.66
4653-59 W Jackson Blvd Chicago, IL 606443 Bedroom 1 Bath Garden3BR,1BA$1.32
5078 W Adams St, Unit 15078 W Adams St3BR,1BA$1.33
208 N Kolin Ave, Unit 3208 N Kolin Ave3BR,1BA$1.38
208 N Kolin Ave, Unit 3208 N Kolin Ave3BR,1BA$1.50
5017 W Huron St, Unit 25017 W Huron St3BR,1BA$1.62
200 N Kenneth2/1.02BR,1BA$1.35
400-08 S Laramie Ave Chicago, IL 606442 Bedroom 1 Bath Apartment2BR,1BA$1.33
5125 W Madison St Chicago, IL 606441 Bedroom 1 Bath Apartment1BR,1BA$1.61
5018 W Jackson Blvd Chicago, IL 606441 Bedroom 1 Bath Apartment1BR,1BA$1.73

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

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Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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Best Neighborhoods to Rent in Near Chicago's Top Employers: A Guide for Renters

A Local Expert's Guide to The 10 Best Chicago Neighborhoods near Major Local Employers. Find your perfect Chicago, IL apartment, condo, or rental home today at ApartmentHomeLiving.com

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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A Local Expert's Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago

A Local Expert's guide to the Best Student Friendly Neighborhoods Near Colleges in the Chicago, IL metro area for affordable living. Find your perfect Chicago Student apartment, condo, or rental home today at ApartmentHomeliving.com

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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.

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Pet Friendly Lifestyle
Madison Square, Chicago, IL

Ranked #84

Among cities in Illinois 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

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 Chicago, IL 60624 listed at $875.

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

The lowest price for a Cheap One Bedroom Madison Square Apartment is $1,080 at 5125 W Madison St Chicago, IL 60644.

What is the most affordable Madison Square Three Bedroom Apartment?

The best deal on a cheap Madison Square Three Bedroom Apartment rental is at 4653-59 W Jackson Blvd Chicago, IL 60644 and starts from $1,830.

Expert Rental Resources

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.

Helpful Local Expert Guides

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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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Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago

Written by: Nicole Harms

With world-class museums lining its streets, Chicago is a place people go to learn. It’s not surprising, therefore, that it’s also home to multiple colleges and universities with national and global reputations.

decorative image for Best Neighborhoods to Rent in Near Chicago's Top Employers article

Best Neighborhoods to Rent in Near Chicago's Top Employers

Written by: Nicole Harms

Whenever life takes me into the city, I’m always impressed with the sheer amount of industry and commerce that it holds. With all of that commerce comes a wide range of employment options.

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Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

Written by: Nicole Harms

From Lake Shore Drive to the O’Hare Airport, the city of Chicago is a study in diversity, resilience, and culture.

Articles, How-To's, and Tips

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.