2 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (200 Rentals)

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property at 5045 W Gladys Ave

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600
Total Monthly Price
$1,600

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

5045 W Gladys Ave

ChicagoIL60644
property at 220 N Laporte Ave

$10,063

Total Monthly Price

Total Monthly Price

Base Rent
$10,063
Total Monthly Price
$10,063

2 Bedroom, 1 Bath Home for Rent

Available Now

220 N Laporte Ave

ChicagoIL60644

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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708 S Karlov
2 Bedroom Apartments

708 S Karlov

708-14 S Karlov AveChicago, IL 60624
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4345 W Wilcox St
2 Bedroom Apartments

4345 W Wilcox St

4345 W Wilcox StChicago, IL 60624

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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4101 W Gladys
2 Bedroom Apartments

4101 W Gladys

4101 W GladysChicago, IL 60624

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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4205 W Gladys
2 Bedroom Apartments

4205 W Gladys

4205 W GladysChicago, IL 60624
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HICA Redevelopment
2 Bedroom Apartments

HICA Redevelopment

5042 W Washington BlvdChicago, IL 60644
  • Smoke Free

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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Pine Race
2 Bedroom Apartments

Pine Race

557-563 N Pine AveChicago, IL 60644
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4134 W Wilcox St
2 Bedroom Apartments

4134 W Wilcox St

4134 W Wilcox StChicago, IL 60624
  • Utilities Included
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131 N Pine Ave
2 Bedroom Apartments

131 N Pine Ave

131 N Pine AveChicago, IL 60644
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726 N Pine Ave
2 Bedroom Apartments

726 N Pine Ave

726 N Pine AveChicago, IL 60644
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163 N Lamon Ave
2 Bedroom Apartments

163 N Lamon Ave

163 N Lamon AveChicago, IL 60644

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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Showing Results 1-50, Page 1 of 4

Madison Square, Chicago, IL Local Guide

Largest Available Madison Square 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in the Madison Square area of Chicago, IL is found at 200 N Kenneth and is listed at 1,000 square feet priced from $1,550. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
200 N Kenneth2/1.01,000 Sq Ft$1,550
Pine North2BR/1.0BA750 Sq Ft$1,200
708 S Karlov2 Bedroom 1 Bath Apartment640 Sq Ft$1,230

Cheapest Available Madison Square 2 Bedroom Apartments

Currently the lowest priced 2 Bedroom apartment unit Madison Square of Chicago, IL is the 2BR/1.0BA Model starting from $1,200 at Pine North. The average price for all 2 Bedroom apartments in Madison Square is currently $1,565. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
Pine North2BR/1.0BA$1,200
708 S Karlov2 Bedroom 1 Bath Apartment$1,230
200 N Kenneth2/1.0$1,550

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

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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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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 2 Bedroom Madison Square Apartments

What is the largest available 2 Bedroom Madison Square Apartment for rent?

Today's apartment with the most square footage in Madison Square is a 1,000 square feet unit starting from $1,550 at 200 N Kenneth.

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.

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

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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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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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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.

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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

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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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