Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (325 Rentals) Page 2 of 7

How Many Bedrooms?Done
Select your price rangeDone
to
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
close
View Me
4911 W Adams St
3 Bedroom Apartments

4911 W Adams St

4911 W Adams StChicago, IL 60644
close
View Me
4700-4702 W Adams St
Studio to 3 Bedroom Apartments

4700-4702 W Adams St

4700-4702 W Adams StChicago, IL 60644
close
View Me
4919 W ADAMS
3 Bedroom Apartments

4919 W ADAMS

4919 W ADAMSChicago, IL 60644
close
View Me
5000 W Monroe St
2 to 3 Bedroom Apartments

5000 W Monroe St

5000 W Monroe 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!

Read Article
close
View Me
163 N Lamon Ave
1 to 3 Bedroom Apartments

163 N Lamon Ave

163 N Lamon AveChicago, IL 60644
close
View Me
4941 W West End
3 Bedroom Apartments

4941 W West End

4941 W West EndChicago, IL 60644
close
View Me
184 N Lamon Ave
2 to 3 Bedroom Apartments

184 N Lamon Ave

184 N Lamon AveChicago, IL 60644
Furnished
close
View Me
W. Washington
1 to 3 Bedroom Apartments

W. Washington

5027-5029 W Washington BlvdChicago, IL 60644
close
View Me
200 N Lamon Ave
1 to 2 Bedroom Apartments

200 N Lamon Ave

200 N Lamon AveChicago, IL 60644

Best Neighborhoods to Rent in Near Chicago's Top Employers: A Guide for Renters

Learn about the best places to live near major employers in Chicago with original content written by our Local Expert Nicole Harms

Read Article
close
View Me
4747 W Fulton St
2 to 3 Bedroom Apartments

4747 W Fulton St

4747 W Fulton StChicago, IL 60644
close
View Me
5019 W Quincy St
1 Bedroom Apartments

5019 W Quincy St

5019 W Quincy StChicago, IL 60644
close
View Me
4948 W Gladys Ave
1 to 2 Bedroom Apartments

4948 W Gladys Ave

4948 W Gladys AveChicago, IL 60644
close
View Me
HICA Redevelopment
1 to 2 Bedroom Apartments

HICA Redevelopment

5042 W Washington BlvdChicago, IL 60644
  • Smoke Free
close
View Me
5019 W Maypole Ave
1 to 2 Bedroom Apartments

5019 W Maypole Ave

5019 W Maypole AveChicago, IL 60644

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

Read Article
close
View Me
4504 W Wilcox St
3 Bedroom Apartments

4504 W Wilcox St

4504 W Wilcox StChicago, IL 60624
close
View Me
4500 W Wilcox St
3 Bedroom Apartments

4500 W Wilcox St

4500 W Wilcox StChicago, IL 60624
close
View Me
Enola Dew Apartments
1 Bedroom Apartments

Enola Dew Apartments

4623 W Gladys AveChicago, IL 60644
Senior Living
close
View Me
223 N Kolmar
2 Bedroom Apartments

223 N Kolmar

223 N KolmarChicago, IL 60624
close
View Me
4501 W Maypole Ave
1 to 4 Bedroom Apartments

4501 W Maypole Ave

4501 W Maypole AveChicago, IL 60624
close
View Me
5137 W Washington
1 to 2 Bedroom Apartments

5137 W Washington

5137 W WashingtonChicago, IL 60644

Chicago's Best Affordable Neighborhoods

Learn about Chicago and the best places to live with original content written by our Chicago, IL Local Expert Nicole Harms

Read Article
close
View Me
4412 W Monroe St
2 to 3 Bedroom Apartments

4412 W Monroe St

4412 W Monroe StChicago, IL 60624
close
View Me
4345 W Wilcox St
1 to 2 Bedroom Apartments

4345 W Wilcox St

4345 W Wilcox StChicago, IL 60624

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

Read Article
Showing Results 51-100, Page 2 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

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

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.

decorative image for Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible article

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.

decorative image for Chicago Relocation 101: Mastering Utilities, Registration, and the CTA article

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.

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

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

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

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.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

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.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

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.