close
View Me
$890Studio Apartments Available Now
Washington Plaza
5501 W Washington BlvdChicago, IL 60644
Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (62 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
22-26 N Pulaski Rd
ChicagoIL60624
close
View Me
$1,040 - $1,1101 to 2 Bedroom Apartments Available Now
Congress Commons
500-514 S Laramie AveChicago, IL 60644
close
View Me
$1,130 - $1,1501 Bedroom Apartments Available Jun 30
330 N Pine Ave
330 N Pine AveChicago, IL 60644
close
View Me
$1,2002 Bedroom Apartments Available Now
5111 W Ferdinand St, Unit 2C
5111 W Ferdinand StChicago, IL 60644
close
View Me
$1,2001 Bedroom Apartments Available Now
4616 W Jackson Blvd, Unit 4616 w Jackson Garden
4616 W Jackson BlvdChicago, IL 60644
320 N Pine Ave, Unit 403
320 N Pine Ave
ChicagoIL60644
346 N Laramie Ave, Unit 2W
346 N Laramie Ave
ChicagoIL60644
close
View Me
Studio to 1 Bedroom Apartments
Garfield Apartments
4342 W Washington BlvdChicago, IL 60624
close
View Me
Studio to 3 Bedroom Apartments
542 N Pine Ave
542 N Pine AveChicago, IL 60644
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.
close
View Me
1 to 3 Bedroom Apartments
La Rose Apartments
5501 W Monroe StChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
123 N Central Ave
123 N Central AveChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
4114 W Washington Blvd
4114 W Washington BlvdChicago, IL 60624
close
View Me
Studio to 1 Bedroom Apartments
5125 W Madison St
5125 W Madison StChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
5001 W Adams St
5001 W Adams StChicago, IL 60644
24 N Pulaski Rd
ChicagoIL60624
close
View Me
Studio to 2 Bedroom Apartments
5201 W Washington Blvd (old)
5201 W Washington BlvdChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5100-5104 W Monroe St
5100-5104 W Monroe StChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
Austin Apartments
723-725 N Central AveChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
Oak Park Apartments
729 N Central AveChicago, 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.
close
View Me
1 to 3 Bedroom Apartments
Austin Apartments
5024-5028 W Quincy StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
600-602 N Lorel Ave
600-602 N Lorel AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5100-5104 W Madison St
5100-5104 W Madison StChicago, IL 60644
close
View Me
1 Bedroom Apartments
5018 W Jackson Blvd
5018 W Jackson BlvdChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
418-424 S Laramie Ave
418-424 S Laramie AveChicago, IL 60644
close
View Me
1 to 4 Bedroom Apartments
Austin Apartments
5101-5103 W Monroe StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5040 W Quincy St
5040 W Quincy StChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
5263 W Congress Pky
5263 W Congress PkyChicago, IL 60644
209 N Kolmar Ave
ChicagoIL60624
close
View Me
1 to 2 Bedroom Apartments
5011-5015 W Maypole Ave
5011-5015 W Maypole AveChicago, IL 60644
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.
close
View Me
1 to 2 Bedroom Apartments
5500 W Van Buren St
5500 W Van Buren StChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
400 S Kilbourn Ave
400 S Kilbourn AveChicago, IL 60624
close
View Me
2 to 3 Bedroom Apartments
Pangea Apartments
5448 W Adams StChicago, IL 60644
close
View Me
1 to 4 Bedroom Apartments
4815 W Monroe St
4815 W Monroe StChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
701 N Lotus Ave
701 N Lotus AveChicago, IL 60644
close
View Me
1 Bedroom Apartments
5012 W Jackson Blvd
5012 W Jackson BlvdChicago, IL 60644
close
View Me
Studio to 2 Bedroom Apartments
Jade Apartments
1-15 N Keeler AveChicago, IL 60624
close
View Me
1 to 2 Bedroom Apartments
5328 W Harrison St
5328 W Harrison StChicago, IL 60644
close
View Me
1 Bedroom Apartments
5015 W Jackson Blvd
5015 W Jackson BlvdChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
708-14 S Karlov Ave
708-14 S Karlov AveChicago, IL 60624
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.
close
View Me
1 to 2 Bedroom Apartments
4641 W Jackson Blvd
4641 W Jackson BlvdChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
4443 W Gladys Ave
4443 W Gladys AveChicago, IL 60624
close
View Me
1 to 3 Bedroom Apartments
5201-5207 W Washington Blvd
5201-5207 W Washington BlvdChicago, IL 60644
close
View Me
Studio to 6 Bedroom Apartments
4152-4156 W Lake St
4152-4156 W Lake StChicago, IL 60624
close
View Me
2 Bedroom Apartments
634 N Lamon Ave
634 N Lamon AveChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
400 S Laramie Ave
400 S Laramie AveChicago, IL 60644
close
View Me
Studio to 4 Bedroom Apartments
654 N Pine Ave
654 N Pine AveChicago, IL 60644
close
View Me
Studio to 3 Bedroom Apartments
109 N Laramie Ave
109 N Laramie AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
200 N Kenneth Ave
200 N Kenneth AveChicago, IL 60624
close
View Me
2 to 3 Bedroom Apartments
148 N La Crosse Ave
148 N La Crosse AveChicago, IL 60644
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
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 | $890 | $890 | $890 |
| Madison Square 1 Bedroom Apartments | $1,115 | $1,000 | $1,200 |
| Madison Square 2 Bedroom Apartments | $1,500 | $1,095 | $2,100 |
| Madison Square 3 Bedroom Apartments | $1,973 | $1,700 | $2,400 |
| Madison Square 4 Bedroom Apartments | $2,346 | $1,740 | $3,500 |
Browse Apartments in this Neighborhood
There are currently 62 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
See all Apartments in ChicagoExplore Chicago
Madison Square, Chicago, IL Local Guide
- Nearby Chicago neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
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 542 N Pine Ave priced from $815. Washington Plaza 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 Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 542 N Pine Ave | 0BR/1.0BA | Studio,1BA | $815 |
| Washington Plaza | Studio Apartment | Studio,1BA | $890 |
| 5125 W Madison | Studio Apartment | Studio,1BA | $895 |
| Austin Apartments | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,085 |
| 500 S Laramie | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1,095 |
| 5001 W Adams St | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,125 |
| 5018 W Jackson Blvd | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,125 |
| 418-424 S Laramie Ave | 1 Bedroom 1 Bath Apartment with Dining | 1BR,1BA | $1,130 |
| 5500 W Van Buren St | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1,155 |
| 400 S Kilbourn Ave | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1,170 |
Best Value Apartments for Rent in Madison Square, IL
As of June 11, 2026 the best value apartment in the Madison Square area is the $1.35 price per square foot 5100 W Fulton St Model at 5100 W Fulton St, Unit 1 in the in the Austin neighborhood starting from $3,500. The second greatest value Madison Square apartment is the 328 N Lockwood Ave Model at 328 N Lockwood Ave, Unit 2 starting at $2,340 with a $0.98 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 5100 W Fulton St, Unit 1 | 5100 W Fulton St | 4BR,2BA | $1.35 |
| 328 N Lockwood Ave, Unit 2 | 328 N Lockwood Ave | 3BR,1BA | $0.98 |
| 217 N Laramie Ave, Unit 1 | 217 N Laramie Ave | 5BR,2BA | $1.08 |
| 5078 W Adams St, Unit 1 | 5078 W Adams St | 3BR,1BA | $1.33 |
| 4306 W Maypole Ave, Unit 1F | 4306 W Maypole Ave | 4BR,1BA | $1.45 |
| 200 N Kenneth Ave | 2/1.0 | 2BR,1BA | $1.30 |
| 109 N Laramie Ave | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.52 |
| Austin Apartments | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.55 |
| Congress Commons | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.68 |
| 542 N Pine Ave | 0BR/1.0BA | Studio ,1BA | $1.52 |
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.
Read Article
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
Read ArticleA 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
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
Read ArticleQuick 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.
Let everyone know!
Do you know the Madison Square area?
If you’re an expert on all things Madison Square, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #92
Among cities in Illinois 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 542 N Pine 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 $1,095 at Congress Commons.
What is the most affordable Madison Square Three Bedroom Apartment?
The best deal on a cheap Madison Square Three Bedroom Apartment rental is at 109 N Laramie Ave and starts from $1,350.
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
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.
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.
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.
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
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.