728 N Pine Ave
ChicagoIL60644
Cheap Homes for Rent in the Madison Square Neighborhood of Chicago, IL from $1,050 (5 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
close
View Me
$1,2001 Bedroom Apartments Available Now
4616 W Jackson Blvd, Unit 4616 w Jackson Garden
4616 W Jackson BlvdChicago, IL 60644
The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Chicago may cost more than the national average, but with the right neighborhood, a smart transit strategy, and a few local insider tips, living well in the Windy City is more achievable than you might think. Our local expert breaks down everything from rent and groceries to transportation and healthcare so you can plan your move with confidence.
close
View Me
$1,2502 Bedroom Apartments Available Now
4622 W Jackson Blvd, Unit 3
4622 W Jackson BlvdChicago, IL 60644
320 N Pine Ave, Unit 403
320 N Pine Ave
ChicagoIL60644
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
4035 W Gladys Ave, Unit 2N
4035 W Gladys Ave
ChicagoIL60624
Showing Results 1-5, Page 1 of 1
Madison Square, Chicago, IL Local Guide
How much does it cost to rent a home in Madison Square?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Madison Square 2 Bedroom Homes for Rent | $1,698 | $1,495 | $1,850 |
| Madison Square 3 Bedroom Homes for Rent | $1,803 | $1,600 | $2,000 |
Browse Homes for Rent in this Neighborhood
There are currently 5 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
Explore Chicago
Madison Square, Chicago, IL Local Guide
- Nearby Chicago neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
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 5001 W Adams priced from $960. 567 N Pine Ave has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,000. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 5001 W Adams | Studio Apartment | Studio,1BA | $960 |
| 567 N Pine Ave | 2B | 1BR,1BA | $1,000 |
| 723 N Central | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,055 |
Best Value Apartments for Rent in Madison Square, IL
As of September 09, 2026 the best value apartment in the Madison Square area is the $1.20 price per square foot 4 Bedroom 1.5 Bath Apartment Model at 654 N Pine in the in the Austin neighborhood starting from $1,925. The second greatest value Madison Square apartment is the 4710 W Jackson Blvd Model at 4710 W Jackson Blvd, Unit 2 starting at $1,500 with a $1.14 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 654 N Pine | 4 Bedroom 1.5 Bath Apartment | 4BR,1.5BA | $1.20 |
| 4710 W Jackson Blvd, Unit 2 | 4710 W Jackson Blvd | 2BR,1BA | $1.14 |
| 5100 W Madison | 3 Bedroom 2 Bath Apartment with Dining | 3BR,2BA | $1.18 |
| 5223-5225 W Washington Blvd | 2 Bed 1 Bath | 2BR,1BA | $1.36 |
| 200 N Kenneth | 2/1.0 | 2BR,1BA | $1.65 |
| Pine St 316-318 | 2BR/1.0BA | 2BR,1BA | $1.39 |
| 400 S Laramie | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.50 |
| 418 S Laramie | 2 Bedroom 1 Bath Apartment with Dining | 2BR,1BA | $1.59 |
| 567 N Pine Ave | 2B | 1BR,1BA | $1.43 |
| 723 N Central | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.56 |
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 ArticleNavigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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 Article
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.
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 #89
Among cities in Illinois for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about Madison Square
What type of rentals are currently available in Madison Square?
There are currently 305 Apartments for Rent in Madison Square, IL with pricing that ranges from $890 to $9,739. There are also 20 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $1,050 to $2,000.
What is the current price range for Rental Homes in Madison Square?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Madison Square ranges from $1,050 to $2,000 with an average monthly rent of $1,707.
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
The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Written by: Nicole Harms
When choosing a place to live, there are many things you must consider. Your employer, your shopping preferences, and even schools are all important to think about. Yet cost of living is also important to know and plan for.
Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
Written by: Nicole Harms
I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.
Chicago Relocation 101: Mastering Utilities, Registration, and the CTA
Written by: Nicole Harms
Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.
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
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.