Apartments for Rent in the Madison Square Neighborhood of Chicago, IL Under $1,500 (60 Rentals)

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Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Looking for a rental near Chicago? These five cities offer excellent options! From small-town charm to excellent business options, you can't go wrong!

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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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4300 W Wilcox St
1 to 3 Bedroom Apartments

4300 W Wilcox St

4300 W Wilcox StChicago, IL 60624
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708 S Karlov
2 to 3 Bedroom Apartments

708 S Karlov

708-14 S Karlov AveChicago, IL 60624
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701 S Karlov
Studio to 3 Bedroom Apartments

701 S Karlov

701 S Karlov AveChicago, IL 60624
  • Utilities Included

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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4725 W maypole
1 to 5 Bedroom Apartments

4725 W maypole

4721-4725 W Maypole AveChicago, IL 60644
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423 N Central
1 to 3 Bedroom Apartments

423 N Central

423 N Central AveChicago, IL 60644
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5556 W Jackson
2 to 4 Bedroom Apartments

5556 W Jackson

5556-5576 W Jackson BlvdChicago, IL 60644
  • Utilities Included
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4814 W Monroe St
2 to 3 Bedroom Apartments

4814 W Monroe St

4814 W Monroe StChicago, IL 60644
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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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5036 W Quincy St
2 to 3 Bedroom Apartments

5036 W Quincy St

5036 W Quincy StChicago, IL 60644
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148 N La Crosse Ave
2 to 3 Bedroom Apartments

148 N La Crosse Ave

148 N La Crosse AveChicago, IL 60644
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5314 W Washington
1 to 3 Bedroom Apartments

5314 W Washington

5201-5207 W Washington BlvdChicago, IL 60644
  • Utilities Included

Chicago Relocation 101: Mastering Utilities, Registration, and the CTA

Moving to Chicago? This essential relocation guide offers a complete checklist for new residents, covering finding the right neighborhood, setting up utilities (ComEd, People’s Gas), and mastering high-rise moving logistics and vehicle registration.

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5500 W Van Buren
1 to 2 Bedroom Apartments

5500 W Van Buren

5500 W Van Buren StChicago, IL 60644
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5015 W Jackson
1 Bedroom Apartments

5015 W Jackson

5015 W Jackson BlvdChicago, IL 60644
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5328 W Harrison
1 to 2 Bedroom Apartments

5328 W Harrison

5328 W Harrison StChicago, IL 60644
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400 S Laramie
2 to 3 Bedroom Apartments

400 S Laramie

400 S Laramie AveChicago, IL 60644
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Jade Apartments
Studio to 2 Bedroom Apartments

Jade Apartments

1-15 N Keeler AveChicago, IL 60624
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5012 W Jackson Blvd
1 Bedroom Apartments

5012 W Jackson Blvd

5012 W Jackson BlvdChicago, IL 60644
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5100 W Monroe
1 to 3 Bedroom Apartments

5100 W Monroe

5100-5104 W Monroe StChicago, IL 60644
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701 N Lotus Ave
2 to 3 Bedroom Apartments

701 N Lotus Ave

701 N Lotus AveChicago, IL 60644
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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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Pangea Apartments
2 to 3 Bedroom Apartments

Pangea Apartments

5448 W Adams StChicago, IL 60644

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!

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1115 S Karlov
Studio to 3 Bedroom Apartments

1115 S Karlov

1115 S Karlov AveChicago, IL 60624
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5024 W Quincy
1 to 3 Bedroom Apartments

5024 W Quincy

5024-5028 W Quincy StChicago, IL 60644
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5011 W Maypole
1 to 2 Bedroom Apartments

5011 W Maypole

5011-5015 W Maypole AveChicago, IL 60644
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5101 W Monroe
1 to 4 Bedroom Apartments

5101 W Monroe

5101-5103 W Monroe StChicago, IL 60644
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5040 W Quincy St
1 to 3 Bedroom Apartments

5040 W Quincy St

5040 W Quincy StChicago, IL 60644
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5018 W Jackson
1 Bedroom Apartments

5018 W Jackson

5018 W Jackson BlvdChicago, IL 60644
  • Utilities Included
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5100 W Madison
1 to 3 Bedroom Apartments

5100 W Madison

5100-5104 W Madison StChicago, IL 60644
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418 S Laramie
1 to 3 Bedroom Apartments

418 S Laramie

418-424 S Laramie AveChicago, 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

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Madison Square, Chicago, IL Local Guide

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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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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 #83

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

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 $1,250 to $1,875. Today's average rental price for Two Bedrooms here is $1,565.

Expert Rental Resources

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.

Helpful Local Expert Guides

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Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Written by: Nicole Harms

I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.

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Chicago Relocation 101: Mastering Utilities, Registration, and the CTA

Written by: Nicole Harms

Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.

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

Written by: Nicole Harms

From Lake Shore Drive to the O’Hare Airport, the city of Chicago is a study in diversity, resilience, and culture.

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Best Neighborhoods to Rent in Near Chicago's Top Employers

Written by: Nicole Harms

Whenever life takes me into the city, I’m always impressed with the sheer amount of industry and commerce that it holds. With all of that commerce comes a wide range of employment options.

Articles, How-To's, and Tips

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.