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Cheap Homes for Rent in Madison Square Neighborhood of Chicago, IL from $1,500 (9 Rentals)
Search the lowest-cost Homes available for rent right now in the Madison Square area of Chicago.
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from $1,2002 Bedroom Apartments Available Now
4622 W Jackson Blvd
4622 W Jackson BlvdChicago, IL 60644
5045 W Gladys Ave
ChicagoIL60644
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.
4133 W Carroll Ave
ChicagoIL60624
4052 W Arthington St
ChicagoIL60624
4040 W Polk St
ChicagoIL60624
822 S Karlov Ave
ChicagoIL60624
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.
555 N Lawler Ave
ChicagoIL60644
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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 | $1,750 | $1,750 | $1,750 |
| Madison Square 3 Bedroom Homes for Rent | $1,875 | $1,500 | $2,550 |
Browse Homes for Rent in this Neighborhood
There are currently 9 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 $840. 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 | $840 |
| 5001 W Adams St | Studio Apartment | Studio,1BA | $955 |
Best Value Apartments for Rent in Madison Square, IL
As of July 13, 2025 the best value apartment in the Madison Square area is the $1.13 price per square foot 4340 W Maypole Ave Model at 4340 W Maypole Ave, Unit Garden Unit in the in the West Garfield Park neighborhood starting from $1,700. The second greatest value Madison Square apartment is the 162 N La Crosse Ave Model at 162 N La Crosse Ave, Unit 2nd Fl. starting at $1,800 with a $1.29 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 Garden Unit | 4340 W Maypole Ave | 2BR,1BA | $1.13 |
| 162 N La Crosse Ave, Unit 2nd Fl. | 162 N La Crosse Ave | 2BR,1BA | $1.29 |
| 4330 W Lexington St, Unit First level | 4330 W Lexington St | 3BR,1BA | $1.36 |
| 423-25 N Central Ave | 3 Bedroom 1 Bath Apartment | 3BR,1BA | $1.62 |
| 200 N Kenneth | 2BR/1.0BA | 2BR,1BA | $1.28 |
| 4814 W Monroe | 2 Bedroom 1 Bathroom Apartment | 2BR,1BA | $1.58 |
| 5328 W Harrison | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.51 |
| 5309 W Jackson Blvd, Unit 2ndfloor | 5309 W Jackson Blvd | 2BR,1BA | $1.30 |
| 5100-04 W Madison St | 2 Bedroom 1 Bathroom Apartment | 2BR,1BA | $1.59 |
| 5201 W Washington Blvd (old) | 2 Bedroom, 1 Bath | 2BR,1BA | $1.63 |
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Frequently Asked Questions about Madison Square
What type of rentals are currently available in Madison Square?
There are currently 303 Apartments for Rent in Madison Square, IL with pricing that ranges from $810 to $2,300. There are also 15 Single Family Homes for rent, Condos, and Townhome rentals currently available in Madison Square ranging from $1,500 to $2,550.
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 $1,500 to $2,550 with an average monthly rent of $1,812.
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.