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$825Studio Apartments Available Now
4114 W Washington Blvd Chicago, IL 60624
4114 W Washington BlvdChicago, IL 60624
Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (12 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
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$890 - $1,130Studio to 1 Bedroom Apartments Available Now
5501 W Washington Blvd Chicago, IL 60644
5501 W Washington BlvdChicago, IL 60644
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$1,005 - $1,1001 to 2 Bedroom Apartments Available Now
500 S Laramie
500-514 S Laramie AveChicago, IL 60644
4039 W Wilcox St
ChicagoIL60624
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$1,0501 Bedroom Apartments Available Now
10 N Long Ave
10 N Long AveChicago, IL 60644
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Studio to 1 Bedroom Apartments
Garfield Apartments
4342 W Washington BlvdChicago, IL 60624
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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Studio to 1 Bedroom Apartments
123 N Central Ave
123 N Central AveChicago, IL 60644
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Studio to 3 Bedroom Apartments
Pine North
542 N Pine AveChicago, IL 60644
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1 to 3 Bedroom Apartments
La Rose Apartments
5501 W Monroe StChicago, IL 60644
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Studio to 2 Bedroom Apartments
5201 W Washington Blvd (old)
5201 W Washington BlvdChicago, IL 60644
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1 to 4 Bedroom Apartments
5101 W Monroe St Chicago, IL 60644
5101-5103 W Monroe StChicago, IL 60644
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Studio to 1 Bedroom Apartments
5125 W Madison St Chicago, IL 60644
5125 W Madison StChicago, 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.
Showing Results 1-12, Page 1 of 1
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 | $893 | $825 | $950 |
| Madison Square 1 Bedroom Apartments | $1,084 | $1,005 | $1,130 |
| Madison Square 2 Bedroom Apartments | $2,972 | $1,100 | $10,000+ |
| Madison Square 3 Bedroom Apartments | $2,396 | $1,400 | $9,559 |
| Madison Square 4 Bedroom Apartments | $2,200 | $2,200 | $2,200 |
Browse Apartments in this Neighborhood
There are currently 12 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
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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 $775. 4114 W Washington Blvd Chicago, IL 60624 has the second lowest priced unit, which is a Studio apartment currently listed from $825. 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 | $775 |
| 4114 W Washington Blvd Chicago, IL 60624 | Studio Apartment | Studio,1BA | $825 |
| 5501 W Washington Blvd Chicago, IL 60644 | Studio Apartment | Studio,1BA | $890 |
| 500 S Laramie | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,005 |
| 5101 W Monroe St Chicago, IL 60644 | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,050 |
Best Value Apartments for Rent in Madison Square, IL
As of January 21, 2026 the best value apartment in the Madison Square area is the $1.23 price per square foot 4644 W Gladys Ave Model at 4644 W Gladys Ave, Unit 1 in the in the West Garfield Park neighborhood starting from $1,600. The second greatest value Madison Square apartment is the 5301 W Jackson Blvd Model at 5301 W Jackson Blvd, Unit 2 starting at $1,400 with a $1.17 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. |
|---|---|---|---|
| 4644 W Gladys Ave, Unit 1 | 4644 W Gladys Ave | 3BR,1BA | $1.23 |
| 5301 W Jackson Blvd, Unit 2 | 5301 W Jackson Blvd | 2BR,1BA | $1.17 |
| 4238 W Grenshaw St, Unit g | 4238 W Grenshaw St | 3BR,1BA | $1.33 |
| 4847 W Washington Blvd, Unit 2 | 4847 W Washington Blvd | 3BR,1BA | $1.50 |
| 148 N La Crosse Ave Chicago, IL 60644 | 3 Bedroom 1 Bath Apartment | 3BR,1BA | $1.18 |
| 200 N Kenneth | 2/1.0 | 2BR,1BA | $1.30 |
| 4157 W Adams | 3/1.0 | 3BR,1BA | $1.45 |
| 4814-4820 W Monroe St Chicago, IL 60644 | 2 Bedroom 1 Bath Garden | 2BR,1BA | $1.36 |
| 4152 W Lake St | 2/1.0 | 2BR,1BA | $1.33 |
| 5448 W Adams St 119-21 N Lotus Chicago, IL 60644 | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.48 |
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 $775.
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 500 S Laramie.
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 $1,100 at Pine North.
What is the most affordable Madison Square Three Bedroom Apartment?
The best deal on a cheap Madison Square Three Bedroom Apartment rental is at 5448 W Adams St 119-21 N Lotus Chicago, IL 60644 and starts from $1,275.
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.
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A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago
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Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!