Apartments for Rent in the Madison Square Neighborhood of Chicago, IL Under $1,500 (45 Rentals)

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Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

Learn about the best things about living in Chicago from a local in the Insiders Guide to Renting in Chicago. Find your perfect Chicago apartment today!

property at 4159 W Adams St

4159 W Adams St

ChicagoIL60624
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5302 W Ohio St
2 to 3 Bedroom Apartments

5302 W Ohio St

5302 W Ohio StChicago, IL 60644
  • Utilities Included
  • Smoke Free
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4443 W Gladys Ave
2 to 3 Bedroom Apartments

4443 W Gladys Ave

4443 W Gladys AveChicago, IL 60624
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4725 W maypole
1 to 5 Bedroom Apartments

4725 W maypole

4721-4725 W Maypole AveChicago, IL 60644

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.

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4700 W Flournoy St
1 to 2 Bedroom Apartments

4700 W Flournoy St

4700 W Flournoy StChicago, IL 60644
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200 N Kenneth
1 to 3 Bedroom Apartments

200 N Kenneth

200 N Kenneth AveChicago, IL 60624
  • Utilities Included
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5036 W Quincy St
2 to 3 Bedroom Apartments

5036 W Quincy St

5036 W Quincy StChicago, IL 60644
  • Utilities Included
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634-640 N Lamon
2 Bedroom Apartments

634-640 N Lamon

634 N Lamon AveChicago, IL 60644
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4152 W Lake St
Studio to 6 Bedroom Apartments

4152 W Lake St

4152-4156 W Lake StChicago, IL 60624
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5500 W Van Buren
1 to 2 Bedroom Apartments

5500 W Van Buren

5500 W Van Buren StChicago, IL 60644
  • Utilities Included
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4814 W Monroe
2 to 3 Bedroom Apartments

4814 W Monroe

4814 W Monroe StChicago, IL 60644
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5015 W Jackson Blvd
1 Bedroom Apartments

5015 W Jackson Blvd

5015 W Jackson BlvdChicago, IL 60644
  • Utilities Included
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729 N Central
1 to 2 Bedroom Apartments

729 N Central

729 N Central AveChicago, IL 60644
  • Utilities Included

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.

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Jade Apartments
Studio to 2 Bedroom Apartments

Jade Apartments

1-15 N Keeler AveChicago, IL 60624
  • Utilities Included
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109 N Laramie Ave
Studio to 3 Bedroom Apartments

109 N Laramie Ave

109 N Laramie AveChicago, IL 60644
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400-02 S Kilbourn Ave
1 to 2 Bedroom Apartments

400-02 S Kilbourn Ave

400 S Kilbourn AveChicago, IL 60624
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5556-64 W Jackson Blvd
2 to 4 Bedroom Apartments

5556-64 W Jackson Blvd

5556-5576 W Jackson BlvdChicago, IL 60644
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Pine North
Studio to 3 Bedroom Apartments

Pine North

542 N Pine AveChicago, IL 60644
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330 N Pine
Studio to 4 Bedroom Apartments

330 N Pine

330 N Pine AveChicago, IL 60644
  • Utilities Included
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4815 W Monroe St
1 to 4 Bedroom Apartments

4815 W Monroe St

4815 W Monroe StChicago, IL 60644
  • Utilities Included
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5125 W Madison St
Studio to 1 Bedroom Apartments

5125 W Madison St

5125 W Madison StChicago, IL 60644

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.

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5236 W Harrison
1 to 3 Bedroom Apartments

5236 W Harrison

5236 W HarrisonChicago, IL 60644
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5314 W Washington Blvd
1 to 3 Bedroom Apartments

5314 W Washington Blvd

5201-5207 W Washington BlvdChicago, IL 60644
  • Utilities Included
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418-24 S Laramie Ave
1 to 3 Bedroom Apartments

418-24 S Laramie Ave

418-424 S Laramie AveChicago, IL 60644
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5101 W Monroe St
1 to 4 Bedroom Apartments

5101 W Monroe St

5101-5103 W Monroe StChicago, IL 60644
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La Rose Apartments
1 to 3 Bedroom Apartments

La Rose Apartments

5501 W Monroe StChicago, IL 60644
  • Utilities Included
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123 N Central Ave
Studio to 1 Bedroom Apartments

123 N Central Ave

123 N Central AveChicago, IL 60644
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Garfield Apartments
Studio to 1 Bedroom Apartments

Garfield Apartments

4342 W Washington BlvdChicago, IL 60624
  • Utilities Included

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

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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The 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.

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A 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

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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.

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Pet Friendly Lifestyle
Madison Square, Chicago, IL

Ranked #130

Among cities in Illinois for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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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.

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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.

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.