Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (325 Rentals) Page 3 of 7

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4320 W Madison St
1 to 3 Bedroom Apartments

4320 W Madison St

4320 W Madison StChicago, IL 60624
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5242 W Adams St
5 Bedroom Apartments

5242 W Adams St

5242 W Adams 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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4300 W Wilcox St
1 to 3 Bedroom Apartments

4300 W Wilcox St

4300 W Wilcox StChicago, IL 60624
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211 N Kolin Ave
1 Bedroom Apartments

211 N Kolin Ave

211 N Kolin AveChicago, IL 60624
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305 N Latrobe Ave
2 to 3 Bedroom Apartments

305 N Latrobe Ave

305 N Latrobe AveChicago, IL 60644
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31 N Lorel Ave
2 to 3 Bedroom Apartments

31 N Lorel Ave

31 N Lorel AveChicago, IL 60644
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211 N Kildare Ave
1 to 4 Bedroom Apartments

211 N Kildare Ave

211 N Kildare AveChicago, IL 60624
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4245 W Maypole Ave
2 to 3 Bedroom Apartments

4245 W Maypole Ave

4245 W Maypole AveChicago, IL 60624
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505 S Lockwood Ave
1 to 2 Bedroom Apartments

505 S Lockwood Ave

505 S Lockwood AveChicago, IL 60644
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4206 W Jackson St
1 to 2 Bedroom Apartments

4206 W Jackson St

4206 W Jackson StChicago, IL 60624
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5442 W Adams St
2 to 3 Bedroom Apartments

5442 W Adams St

5442 W Adams StChicago, IL 60644
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4205 W Gladys
2 to 3 Bedroom Apartments

4205 W Gladys

4205 W GladysChicago, IL 60624
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4134 W Wilcox St
1 to 4 Bedroom Apartments

4134 W Wilcox St

4134 W Wilcox StChicago, IL 60624
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4836 W Erie St
5 Bedroom Apartments

4836 W Erie St

4836 W Erie StChicago, IL 60644
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311-315 N Long Ave
Studio to 3 Bedroom Apartments

311-315 N Long Ave

311-315 N Long AveChicago, IL 60644
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4300 W Flournoy St
2 to 3 Bedroom Apartments

4300 W Flournoy St

4300 W Flournoy StChicago, IL 60624
Showing Results 101-150, Page 3 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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Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

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Articles, How-To's, and Tips

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

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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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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.