Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (325 Rentals) Page 4 of 7

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4317 W Flournoy St
1 to 2 Bedroom Apartments

4317 W Flournoy St

4317 W Flournoy StChicago, IL 60624
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4121 W Jackson Blvd
Studio to 2 Bedroom Apartments

4121 W Jackson Blvd

4121 W Jackson BlvdChicago, IL 60624
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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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139 N Pine Ave
2 Bedroom Apartments

139 N Pine Ave

139 N Pine AveChicago, IL 60644
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600 Laramie
1 to 3 Bedroom Apartments

600 Laramie

600 LaramieChicago, IL 60644
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4042 W Wilcox St
Studio to 4 Bedroom Apartments

4042 W Wilcox St

4042 W Wilcox StChicago, IL 60624
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4036 W Monroe St
3 Bedroom Apartments

4036 W Monroe St

4036 W Monroe StChicago, IL 60624
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4101 W Gladys
1 to 3 Bedroom Apartments

4101 W Gladys

4101 W GladysChicago, IL 60624
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4037 W Monroe St
1 to 3 Bedroom Apartments

4037 W Monroe St

4037 W Monroe StChicago, IL 60624
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5521 W Gladys Ave
1 to 2 Bedroom Apartments

5521 W Gladys Ave

5521 W Gladys AveChicago, IL 60644
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4049 W Jackson Blvd
Studio to 2 Bedroom Apartments

4049 W Jackson Blvd

4049 W Jackson BlvdChicago, IL 60624
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5318 W Race Ave
Studio Apartments

5318 W Race Ave

5318 W Race AveChicago, IL 60644
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4801 W Chicago Ave
1 Bedroom Apartments

4801 W Chicago Ave

4801 W Chicago AveChicago, IL 60651
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601 N Lockwood Ave
2 to 3 Bedroom Apartments

601 N Lockwood Ave

601 N Lockwood AveChicago, IL 60644
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4016 W Wilcox St
1 Bedroom Apartments

4016 W Wilcox St

4016 W Wilcox StChicago, IL 60624
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5317 W Ohio St
1 Bedroom Apartments

5317 W Ohio St

5317 W Ohio StChicago, IL 60644
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4031 W Gladys Ave
2 to 3 Bedroom Apartments

4031 W Gladys Ave

4031 W Gladys AveChicago, IL 60624
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700 N Laramie Ave
Studio to 2 Bedroom Apartments

700 N Laramie Ave

700 N Laramie AveChicago, IL 60644
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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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420 N Pine Ave
2 Bedroom Apartments

420 N Pine Ave

420 N Pine AveChicago, IL 60644
Showing Results 151-200, Page 4 of 7

Frequently Asked Questions about Madison Square

What is the current pricing and availability for apartments for rent in the Madison Square area of Chicago, IL?

As of today, August 18, 2026, there are currently 325 available Madison Square apartments priced from $890 to $10,063, with an average monthly rent of $1,931.

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 $975 to $1,200 with an average monthly rent of $1,075.

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 $1,110 to $10,063. Today's average rental price for Two Bedrooms here is $2,422.

How expensive are Madison Square Three Bedroom Apartments?

There are currently 121 Three Bedroom Apartments listings available in Madison Square on ApartmentHomeLiving.com. The pricing ranges from $1,350 to $2,175 - averaging $1,808 for the location.

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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The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago

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When choosing a place to live, there are many things you must consider. Your employer, your shopping preferences, and even schools are all important to think about. Yet cost of living is also important to know and plan for.

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

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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

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

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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.

Articles, How-To's, and Tips

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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

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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

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.