close
View Me
Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $600 (6 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
close
View Me
$865Studio to 1 Bedroom Apartments Contact Us For Availability
4114 W Washington Blvd
4114 W Washington BlvdChicago, IL 60624
close
View Me
$875 - $1,190Studio to 2 Bedroom Apartments Contact Us For Availability
Washington Plaza
5501 W Washington BlvdChicago, IL 60644
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.
close
View Me
close
View Me
close
View Me
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 1-6, 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 | $870 | $865 | $875 |
| Madison Square 1 Bedroom Apartments | $885 | $650 | $1,190 |
| Madison Square 2 Bedroom Apartments | $3,339 | $1,165 | $10,000+ |
| Madison Square 3 Bedroom Apartments | $2,076 | $1,300 | $8,035 |
| Madison Square 4 Bedroom Apartments | $1,850 | $1,850 | $1,850 |
Browse Apartments in this Neighborhood
There are currently 6 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
See all Apartments in ChicagoExplore Chicago
Madison Square, Chicago, IL Local Guide
- Nearby Chicago neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Madison Square Apartments for Rent
The cheapest available apartment rental in the Madison Square area of Chicago, IL is a 1 Bed unit found at 5101 W Monroe St priced from $1,045. 418-24 S Laramie Ave has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,050. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 5101 W Monroe St | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,045 |
| 418-24 S Laramie Ave | 1 Bedroom 1 Bathroom Apartment | 1BR,1BA | $1,050 |
| 5236 W Harrison | 1 Bedroom 1 Bath Apartment with dining | 1BR,1BA | $1,065 |
Best Value Apartments for Rent in Madison Square, IL
As of December 02, 2025 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 4238 W Grenshaw St Model at 4238 W Grenshaw St, Unit g starting at $1,600 with a $1.33 price per square foot in the Lawndale 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 |
| 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 | $1.38 |
| 5301 W Jackson Blvd, Unit 2 | 5301 W Jackson Blvd | 2BR,1BA | $1.17 |
| 4815 W Monroe St | 3 Bedrooms | 3BR,2BA | $1.43 |
| 200 N Kenneth | 2BR/1.0BA | 2BR,1BA | $1.35 |
| 4814 W Monroe | 2 Bedroom 1 Bathroom Garden Apartment | 2BR,1BA | $1.39 |
| Pine North | 2BR/1.0BA | 2BR,1BA | $1.53 |
| 400-08 S Laramie Ave | 2 Bedroom 1 Bathroom Apartment | 2BR,1BA | $1.57 |
| 5125 W Madison St | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.62 |
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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
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 ArticleQuick 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 #132
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 types of apartments are the cheapest in Madison Square?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 1 regular apartments in Madison Square that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
How do the prices of cheap apartments compare to the average apartment in Madison Square?
Cheap apartments in Madison Square have an average cost of $129 which is $1,721 cheaper than the average rent for all rentals in Madison Square.
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
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!
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.