
Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (311 Rentals)


4114 W Washington Blvd

5423 W West End Ave, Unit 1E

162 N La Crosse Ave, Unit 2nd Fl.

4340 W Maypole Ave, Unit Garden Unit

4238 W Grenshaw St, Unit g

4513 W West End Ave, Unit 2

4330 W Lexington St, Unit First level
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

5259 W Lexington St, Unit 1

4447 W Carroll Ave

4035 W Gladys Ave

4334 W Monroe St
Chicago's Best Affordable Neighborhoods
Learn about Chicago and the best places to live with original content written by our Chicago, IL Local Expert Nicole Harms

5331 W Congress Pkwy

5354 W Madison St

5356 W Madison St

228 N Pine Ave

5344 W Madison St

4429 W Adams St
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.
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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 | $835 | $835 | $835 |
Madison Square 1 Bedroom Apartments | $1,097 | $1,095 | $1,100 |
Madison Square 2 Bedroom Apartments | $1,491 | $900 | $1,860 |
Madison Square 3 Bedroom Apartments | $1,680 | $1,300 | $1,900 |
Madison Square 4 Bedroom Apartments | $1,716 | $1,500 | $1,850 |
Browse Apartments in this Neighborhood
There are currently 311 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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Quick 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.
Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #140
Among cities in Illinois for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about Madison Square
What does renting a Two Bedroom Apartment in Madison Square cost?
The monthly rent prices of Two Bedroom Apartments currently available in Madison Square range from $900 to $1,860. Today's average rental price for Two Bedrooms here is $1,491.
How expensive are Madison Square Three Bedroom Apartments?
There are currently 105 Three Bedroom Apartments listings available in Madison Square on ApartmentHomeLiving.com. The pricing ranges from $1,300 to $1,900 - averaging $1,680 for the location.
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.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

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.