
2 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (200 Rentals) Page 4 of 4


5315 W Washington Blvd

567 N Pine Ave

219-227 N Central Ave

5032 W Washington Blvd

431-439 N Central Ave

4949-4955 W Fulton St

5000 W Quincy St

4856-4858 W Washington Blvd

169 N LeClaire Ave

4739-41 W West End Ave

Pine Building

230-234 N Pine Ave

238 N Pine Ave

5096 W Monroe St

120 N Kilpatrick

Anathoth Gardens

4945-4951 W Monroe St

327 N Pine Ave

Whitmore Apartments

Pine Race II Apartments

130 N Leamington Ave

Washington Pine Apartments

Washington Court

5440 W Ferdinand St

5322 W Washington Ave

Ativie Tower Apartments

Boulevard Commons

318 N Lotus Ave

Central Pine

347-351 S Central Ave

Jackson Terrace

5001 W Washington Blvd

729 N Central

600-602 N Lorel Ave

5040 W Quincy St

5011 W Maypole

5024 W Quincy

1115 S Karlov

723 N Central

148 N La Crosse Ave

109 N Laramie Ave

4814 W Monroe St

5556 W Jackson

423 N Central

4725 W maypole

701 S Karlov

5236 W Harrison

4653 W Jackson Blvd

654 N Pine
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 | $1,086 | $975 | $1,150 |
Madison Square 2 Bedroom Apartments | $1,565 | $1,250 | $1,875 |
| Madison Square 3 Bedroom Apartments | $2,000 | $1,700 | $2,300 |
| Madison Square 4 Bedroom Apartments | $1,800 | $1,800 | $1,800 |
Browse Apartments in this Neighborhood
There are currently 200 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
See all Apartments in ChicagoExplore Chicago
Frequently Asked Questions about 2 Bedroom Madison Square Apartments
What is the largest available 2 Bedroom Madison Square Apartment for rent?
Today's apartment with the most square footage in Madison Square is a 1,000 square feet unit starting from $1,550 at 200 N Kenneth.
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

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.

Best Neighborhoods to Rent in Near Chicago's Top Employers
Written by: Nicole Harms
Whenever life takes me into the city, I’m always impressed with the sheer amount of industry and commerce that it holds. With all of that commerce comes a wide range of employment options.
Articles, How-To's, and Tips

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.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.