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1 to 4 Bedroom Apartments
721 S Karlov Ave
721 S Karlov AveChicago, IL 60624
Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (325 Rentals) Page 5 of 7
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2 Bedroom Apartments
4035 W Lexington St
4035 W Lexington StChicago, IL 60624
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2 Bedroom Apartments
Pine Race
557-563 N Pine AveChicago, IL 60644
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2 Bedroom Apartments
5301-5311 W Chicago Ave
5301-5311 W Chicago AveChicago, IL 60651
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1 to 2 Bedroom Apartments
746-754 N Lorel Ave
746-754 N Lorel AveChicago, IL 60644
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Studio Apartments
4111 W Grenshaw St
4111 W Grenshaw StChicago, IL 60624
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2 Bedroom Apartments
4101 W Grenshaw St
4101 W Grenshaw StChicago, IL 60624
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Studio to 2 Bedroom Apartments
726 N Pine Ave
726 N Pine AveChicago, IL 60644
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1 to 3 Bedroom Apartments
701 N Central Ave
701 N Central AveChicago, IL 60644
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1 Bedroom Apartments
5457-5473 W Chicago Ave
5457-5473 W Chicago AveChicago, IL 60651
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2 Bedroom Apartments
737 N Central Ave
737 N Central AveChicago, IL 60644
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2 to 3 Bedroom Apartments
4814 W Monroe St
4814 W Monroe StChicago, IL 60644
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1 to 4 Bedroom Apartments
4815 W Monroe
4815 W Monroe StChicago, IL 60644
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1 to 3 Bedroom Apartments
4834 W Adams St
4834 W Adams StChicago, IL 60644
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2 to 3 Bedroom Apartments
4856-4858 W Washington Blvd
4856-4858 W Washington BlvdChicago, IL 60644
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Studio to 3 Bedroom Apartments
4739-41 W West End Ave
4739-41 W West End AveChicago, IL 60644
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2 Bedroom Apartments
120 N Kilpatrick
120-122 N Kilpatrick AveChicago, IL 60644
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2 to 3 Bedroom Apartments
148 N La Crosse Ave
148 N La Crosse AveChicago, IL 60644
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Studio to 3 Bedroom Apartments
4945-4951 W Monroe St
4945-4951 W Monroe StChicago, IL 60644
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Studio Apartments
5001 W Monroe St
5001 W Monroe StChicago, IL 60644
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2 to 3 Bedroom Apartments
Ativie Tower Apartments
4955-4959 W Washington BlvdChicago, IL 60644
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Studio Apartments
4952 W Madison St
4952 W Madison StChicago, IL 60644
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Studio to 1 Bedroom Apartments
5001 W Adams
5001 W Adams StChicago, IL 60644
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1 to 5 Bedroom Apartments
4725 W maypole
4721-4725 W Maypole AveChicago, IL 60644
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1 to 2 Bedroom Apartments
Jackson Terrace
4900 W Jackson BlvdChicago, IL 60644
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1 to 3 Bedroom Apartments
5001 W Washington Blvd
5001 W Washington BlvdChicago, IL 60644
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2 to 3 Bedroom Apartments
5000 W Quincy St
5000 W Quincy StChicago, IL 60644
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1 to 3 Bedroom Apartments
5024 W Quincy
5024-5028 W Quincy StChicago, IL 60644
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1 to 3 Bedroom Apartments
4653 W Jackson Blvd
4653-4659 W Jackson BlvdChicago, IL 60644
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1 to 2 Bedroom Apartments
4641 W Jackson Blvd
4641 W Jackson BlvdChicago, IL 60644
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Studio to 1 Bedroom Apartments
4660 W Maypole Ave
4660 W Maypole AveChicago, IL 60644
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1 Bedroom Apartments
5012 W Jackson Blvd
5012 W Jackson BlvdChicago, IL 60644
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2 to 3 Bedroom Apartments
5036 W Quincy St
5036 W Quincy StChicago, IL 60644
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2 to 3 Bedroom Apartments
5032 W Washington Blvd
5032 W Washington BlvdChicago, IL 60644
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2 Bedroom Apartments
21 Units /// Austin
315-325 S Kilpatrick AveChicago, IL 60644
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1 Bedroom Apartments
5018 W Jackson
5018 W Jackson BlvdChicago, IL 60644
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1 to 3 Bedroom Apartments
5040 W Quincy St
5040 W Quincy StChicago, IL 60644
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1 Bedroom Apartments
5007 W Jackson Blvd
5007 W Jackson BlvdChicago, IL 60644
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1 Bedroom Apartments
5015 W Jackson
5015 W Jackson BlvdChicago, IL 60644
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1 to 2 Bedroom Apartments
5011 W Maypole
5011-5015 W Maypole AveChicago, IL 60644
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1 Bedroom Apartments
5019 W Jackson Blvd
5019 W Jackson BlvdChicago, IL 60644
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1 to 3 Bedroom Apartments
5100 W Madison
5100-5104 W Madison StChicago, IL 60644
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1 to 3 Bedroom Apartments
5096 W Monroe St
5096 W Monroe StChicago, IL 60644
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1 to 2 Bedroom Apartments
4949-4955 W Fulton St
4949-4955 W Fulton StChicago, IL 60644
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Studio to 1 Bedroom Apartments
5125 W Madison
5125 W Madison StChicago, IL 60644
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Studio Apartments
New Horizon Apartments
4455 W West End AveChicago, IL 60624
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1 to 4 Bedroom Apartments
5101 W Monroe
5101-5103 W Monroe StChicago, IL 60644
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1 to 3 Bedroom Apartments
5100 W Monroe
5100-5104 W Monroe StChicago, IL 60644
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Studio to 3 Bedroom Apartments
169 N LeClaire Ave
169 N LeClaire AveChicago, IL 60644
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1 to 3 Bedroom Apartments
200 N Kenneth
200 N Kenneth AveChicago, IL 60624
Showing Results 201-250, Page 5 of 7
Madison Square, Chicago, IL Local Guide
How much does it cost to rent an apartment in Madison Square?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Madison Square Studio Apartments | $890 | $890 | $890 |
| Madison Square 1 Bedroom Apartments | $1,075 | $975 | $1,200 |
| Madison Square 2 Bedroom Apartments | $2,422 | $1,110 | $10,000+ |
| Madison Square 3 Bedroom Apartments | $1,808 | $1,350 | $2,175 |
| Madison Square 4 Bedroom Apartments | $1,800 | $1,800 | $1,800 |
How much does it cost to rent a home in Madison Square?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $1,602 | $1,400 | $1,775 |
| 3 Bedroom Homes | $1,710 | $1,500 | $1,950 |
| 4 Bedroom Homes | $2,200 | $1,700 | $2,500 |
Browse Apartments in this Neighborhood
There are currently 325 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
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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
The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Written by: Nicole Harms
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.
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.
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.
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.
Articles, How-To's, and Tips
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.
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.
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.
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.