Apartments for Rent in the Madison Square Neighborhood of Chicago, IL Under $2,000 (56 Rentals)

Washington Plaza

4114 W Washington Blvd

4058 W Congress Pky, Unit 4058-2S

4743 W Jackson Blvd, Unit 1st floor

4238 W Grenshaw St, Unit g

4847 W Washington Blvd, Unit 2

5301 W Jackson Blvd, Unit 2
Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago
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5005 W Ferdinand St, Unit 5005 w unit #1

4827 W Van Buren St

4344 W Lexington St

4035 W Harrison St
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4159 W Adams St

4955 W Washington Blvd
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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.
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Navigating the Rental Market: Tips for First-Time Renters
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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 | $869 | $865 | $875 |
| Madison Square 1 Bedroom Apartments | $1,133 | $1,050 | $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 56 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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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 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.
Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #130
Among cities in Illinois for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about Madison Square
How much are Studio apartments in Madison Square?
There are currently 70 Studio Apartments in Madison Square with rent ranges from $865 to $875 with an average price of $869.
What is the current price range for One Bedroom Madison Square Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Madison Square ranges from $1,050 to $1,190 with an average monthly rent of $1,133.
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 $1,165 to $11,128. Today's average rental price for Two Bedrooms here is $3,339.
How expensive are Madison Square Three Bedroom Apartments?
There are currently 129 Three Bedroom Apartments listings available in Madison Square on ApartmentHomeLiving.com. The pricing ranges from $1,300 to $8,035 - averaging $2,076 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.

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.




































