close
View Me
1 to 3 Bedroom Apartments
130 N Leamington Ave
130 N Leamington AveChicago, IL 60644
Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (325 Rentals) Page 6 of 7
close
View Me
Studio to 3 Bedroom Apartments
109 N Laramie Ave
109 N Laramie AveChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
4400 W Washington Blvd
4400 W Washington BlvdChicago, IL 60624
close
View Me
Studio to 2 Bedroom Apartments
5201 W Washington Blvd (old)
5201 W Washington BlvdChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5314 W Washington
5201-5207 W Washington BlvdChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
Bethel Pace Center
4349-4357 W Washington BlvdChicago, IL 60624
close
View Me
1 to 2 Bedroom Apartments
400 S Kilbourn Ave
400 S Kilbourn AveChicago, IL 60624
close
View Me
Studio to 4 Bedroom Apartments
5200-5210 W Quincy St
5200-5210 W Quincy StChicago, IL 60644
close
View Me
Studio Apartments
4505-4509 W Van Buren St
4505-4509 W Van Buren StChicago, IL 60624
close
View Me
Studio to 1 Bedroom Apartments
Garfield Apartments
4342 W Washington BlvdChicago, IL 60624
close
View Me
1 to 2 Bedroom Apartments
4700 W Flournoy
4700 W Flournoy StChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
400 S Laramie
400 S Laramie AveChicago, IL 60644
close
View Me
1 Bedroom Apartments
5260 W Adams St
5260 W Adams StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
418 S Laramie
418-424 S Laramie AveChicago, IL 60644
close
View Me
Studio to 3 Bedroom Apartments
5315 W Washington Blvd
5315 W Washington BlvdChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5322 W Washington Ave
5322 W Washington AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
16-18 N Lorel Ave
16-18 N Lorel AveChicago, IL 60644
close
View Me
2 Bedroom Apartments
518 S Laramie Ave
518 S Laramie AveChicago, IL 60644
close
View Me
4 Bedroom Apartments
4240-4242 W Adams St
4240-4242 W Adams StChicago, IL 60624
close
View Me
2 to 4 Bedroom Apartments
5334-5362 W Madison St
5334-5362 W Madison StChicago, IL 60644
close
View Me
Studio to 2 Bedroom Apartments
5235 W Lake St
5235 W Lake StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5236 W Harrison
5236 W HarrisonChicago, IL 60644
close
View Me
Studio to 2 Bedroom Apartments
Anathoth Gardens
34 N Keeler AveChicago, IL 60624
close
View Me
Studio to 2 Bedroom Apartments
Jade Apartments
1-15 N Keeler AveChicago, IL 60624
close
View Me
1 to 2 Bedroom Apartments
5263 W Congress
5263 W Congress PkyChicago, IL 60644
close
View Me
3 Bedroom Apartments
4157 W Adams
4157-4159 W Adams StChicago, IL 60624
close
View Me
1 to 4 Bedroom Apartments
Washington Lotus
5417-5429 W Washington BlvdChicago, IL 60644
close
View Me
1 to 4 Bedroom Apartments
Washington Court
5424 W Washington BlvdChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
Pangea Apartments
5448 W Adams StChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
5328 W Harrison
5328 W Harrison StChicago, IL 60644
close
View Me
2 Bedroom Apartments
634 N Lamon
634 N Lamon AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
La Rose Apartments
5501 W Monroe StChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
4114 W Washington
4114 W Washington BlvdChicago, IL 60624
close
View Me
1 Bedroom Apartments
5119-5121 W Ohio Ave
5119-5121 W Ohio AveChicago, IL 60644
close
View Me
Studio to 6 Bedroom Apartments
4152 W Lake
4152-4156 W Lake StChicago, IL 60624
close
View Me
Studio Apartments
Washington villa
4100 W Washington BlvdChicago, IL 60624
close
View Me
1 Bedroom Apartments
509-511 N Lockwood Ave
509-511 N Lockwood AveChicago, IL 60644
close
View Me
2 Bedroom Apartments
Pine Building
7-13 N Pine AveChicago, IL 60644
close
View Me
1 Bedroom Apartments
51-57 N Pine Ave
51-57 N Pine AveChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
5500 W Van Buren
5500 W Van Buren StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5518 W Jackson
5518-20 W Jackson BlvdChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
318 N Lotus Ave
318 N Lotus AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
Washington Pine Apartments
5500-5517 W Washington BlvdChicago, IL 60644
close
View Me
2 to 4 Bedroom Apartments
5556 W Jackson
5556-5576 W Jackson BlvdChicago, IL 60644
close
View Me
1 Bedroom Apartments
51 N Central Ave
51 N Central AveChicago, IL 60644
close
View Me
Studio to 2 Bedroom Apartments
327 N Pine Ave
327 N Pine AveChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
123 N Central Ave
123 N Central AveChicago, IL 60644
close
View Me
Studio Apartments
5412 W Ferdinand
5412 W Ferdinand StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
127 Central
127 N Central AveChicago, IL 60644
close
View Me
2 to 4 Bedroom Apartments
230-234 N Pine Ave
230-234 N Pine AveChicago, IL 60644
Showing Results 251-300, Page 6 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.
See all Apartments in ChicagoExplore Chicago
Let everyone know!
Do you know the Madison Square area?
If you’re an expert on all things Madison Square, tell us what you love (and don't) by rating it and writing a review.
Write a Review
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.