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from $795Studio to 1 Bedroom Apartments Available Now
4114 W Washington Blvd
4114 W Washington BlvdChicago, IL 60624
Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (11 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
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from $825Studio to 2 Bedroom Apartments Available Now
Washington Plaza
5501 W Washington BlvdChicago, IL 60644
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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from $895Studio to 2 Bedroom Apartments Available Now
5957 W Madison St
5957 W Madison StChicago, IL 60644
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The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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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 | $847 | $795 | $910 |
| Madison Square 1 Bedroom Apartments | $1,301 | $1,015 | $1,509 |
| Madison Square 2 Bedroom Apartments | $1,531 | $1,250 | $1,860 |
| Madison Square 3 Bedroom Apartments | $1,904 | $1,535 | $2,449 |
| Madison Square 4 Bedroom Apartments | $2,125 | $2,000 | $2,250 |
Browse Apartments in this Neighborhood
There are currently 11 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
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Madison Square, Chicago, IL Local Guide
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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 Pine North priced from $765. 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 Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Pine North | 0BR/1.0BA | Studio,1BA | $765 |
| 4114 W Washington Blvd | Studio Apartment | Studio,1BA | $795 |
| Washington Plaza | Studio Apartment | Studio,1BA | $825 |
| 5957 W Madison St | Studio Apartment | Studio,1BA | $895 |
| 5001 W Adams St | Studio Apartment | Studio,1BA | $960 |
Best Value Apartments for Rent in Madison Square, IL
As of June 13, 2025 the best value apartment in the Madison Square area is the $0.43 price per square foot 4340 W Maypole Ave Model at 4340 W Maypole Ave, Unit 2 in the in the West Garfield Park neighborhood starting from $1,950. The second greatest value Madison Square apartment is the 5100 W Fulton St Model at 5100 W Fulton St, Unit 1 starting at $2,250 with a $0.87 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. |
|---|---|---|---|
| 4340 W Maypole Ave, Unit 2 | 4340 W Maypole Ave | 3BR,1BA | $0.43 |
| 5100 W Fulton St, Unit 1 | 5100 W Fulton St | 4BR,2BA | $0.87 |
| 4117 W Wilcox St, Unit 1 | 4117 W Wilcox St | 3BR,1BA | $1.06 |
| 5547 W Congress Pky, Unit 3 Bedroom Apartment | 5547 W Congress Pky | 3BR,1BA | $1.10 |
| 4330 W Lexington St, Unit First level | 4330 W Lexington St | 3BR,1BA | $1.60 |
| 5100-04 W Madison St | 3 Bedroom 2 Bathroom Apartment | 3BR,2BA | $1.13 |
| 423-25 N Central Ave | 3 Bedroom 1 Bath Apartment | 3BR,1BA | $1.58 |
| 5040 W Quincy St | 3 Bedroom 1 Bathroom Apartment | 3BR,1BA | $1.22 |
| 5024 W Quincy St | 3 Bedroom 1 Bath Apartment | 3BR,1BA | $1.58 |
| 4814 W Monroe | 2 Bedroom 1 Bathroom Garden Apartment | 2BR,1BA | $1.44 |
Quick Rent Budget Calculator
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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #84
Among neighborhoods in Chicago, IL 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 Pine North listed at $765.
How much is rent for a Cheap One Bedroom Madison Square Apartment?
The lowest price for a Cheap One Bedroom Madison Square Apartment is $1,005 at 701 S Karlov Ave.
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 $1,155 at 4814 W Monroe.
What is the most affordable Madison Square Three Bedroom Apartment?
The best deal on a cheap Madison Square Three Bedroom Apartment rental is at 5040 W Quincy St and starts from $1,085.
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.
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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.