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$825 - $1,130Studio to 2 Bedroom 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 (12 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
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$845 - $880Studio to 1 Bedroom Apartments Available Now
4114 W Washington Blvd
4114 W Washington BlvdChicago, IL 60624
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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.
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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.
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 | $860 | $825 | $900 |
| Madison Square 1 Bedroom Apartments | $1,035 | $925 | $1,130 |
| Madison Square 2 Bedroom Apartments | $1,312 | $1,100 | $1,650 |
| Madison Square 3 Bedroom Apartments | $1,750 | $1,400 | $2,600 |
| Madison Square 4 Bedroom Apartments | $1,950 | $1,700 | $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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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 $815. Washington Plaza 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 | $815 |
| Washington Plaza | Studio Apartment | Studio,1BA | $825 |
| 4114 W Washington Blvd | Studio Apartment | Studio,1BA | $845 |
| 5101 W Monroe St | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,115 |
| 4815 W Monroe St | 1 Bedroom | 1BR,1BA | $1,150 |
Best Value Apartments for Rent in Madison Square, IL
As of October 15, 2025 the best value apartment in the Madison Square area is the $1.23 price per square foot 4903 W Hubbard St Model at 4903 W Hubbard St, Unit 2 in the in the Austin neighborhood starting from $1,850. 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 $1,650 with a $1.18 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. |
|---|---|---|---|
| 4903 W Hubbard St, Unit 2 | 4903 W Hubbard St | 3BR,1BA | $1.23 |
| 162 N La Crosse Ave, Unit 2nd Fl. | 162 N La Crosse Ave | 2BR,1BA | $1.18 |
| 4644 W Gladys Ave, Unit 1 | 4644 W Gladys Ave | 3BR,1BA | $1.31 |
| 4238 W Grenshaw St, Unit g | 4238 W Grenshaw St | 3BR,1BA | $1.33 |
| 708-14 S Karlov Ave | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.29 |
| 200 N Kenneth | 2BR/1.0BA | 2BR,1BA | $1.28 |
| 238 N Lockwood Ave | 238 N Lockwood Ave | 3BR,1BA | $1.50 |
| 5236 W Harrison | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.58 |
| 729 N Central | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.72 |
| 4815 W Monroe St | 1 Bedroom | 1BR,1BA | $1.64 |
Quick Rent Budget Calculator
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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #136
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 Pine North listed at $815.
How much is rent for a Cheap One Bedroom Madison Square Apartment?
The lowest price for a Cheap One Bedroom Madison Square Apartment is $1,050 at Pine North.
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 $1,150 at Pine North.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.