
3 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (130 Rentals)


5422 W Jackson Blvd, Unit 2

734 N Laramie Ave, Unit 2

4249 W Maypole Ave, Unit 1

209 N Kolmar Ave

4938 W Monroe St

4849 W Gladys Ave

5029 W Washington Blvd

5028 W Madison St

607 N Central Ave
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5026 W Madison St

155 N La Crosse Ave

4443 W Gladys Ave

5567 W Van Buren St

4300 W Wilcox St

4836 W West End Ave

158-160 N Laramie Ave

4919 W ADAMS

4320 W Madison St

4340 W Congress Pky
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4911 W Adams St

5573 W Van Buren St

5442 W Adams St

148-150 N La Crosse Ave

31 N Lorel Ave

4110 W Washington Blvd

5014-5018 W West End Ave

4941 W West End

4701 W Van Buren St

311-315 N Long Ave
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Moving to Chicago? This essential relocation guide offers a complete checklist for new residents, covering finding the right neighborhood, setting up utilities (ComEd, People’s Gas), and mastering high-rise moving logistics and vehicle registration.

600 Laramie

5234 W Washington Blvd

4412 W Monroe St

4701 W West End Ave

4504 W Wilcox St

5000 W Monroe St

4347 W Van Buren St

4700-4702 W Adams St

4718 W Congress Pky

701 N Central Ave
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5316 W Washington Blvd

4500 W Wilcox St

5448-5450 W Quincy St

4401 W Jackson Blvd

4031 W Gladys Ave

4712 W Monroe St

4300 W Flournoy St

5501 W Congress Pky

4245 W Maypole Ave

601 N Lockwood Ave
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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 130 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
See all Apartments in ChicagoExplore Chicago
Madison Square, Chicago, IL Local Guide
- Nearby Chicago neighborhoods
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Largest Available Madison Square 3 Bedroom Apartments
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| 5100 W Madison | 3 Bedroom 2 Bath Apartment with Dining | 1,150 Sq Ft | $1,355 |
| 4157 W Adams | 3/1.0 | 1,000 Sq Ft | $2,100 |
Cheapest Available Madison Square 3 Bedroom Apartments
Currently the lowest priced 3 Bedroom apartment unit Madison Square of Chicago, IL is the 3 Bedroom 2 Bath Apartment with Dining Model starting from $1,355 at 5100 W Madison. The average price for all 3 Bedroom apartments in Madison Square is currently $2,000. Here is today’s list of the cheapest available 3 Bedroom options in the area:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| 5100 W Madison | 3 Bedroom 2 Bath Apartment with Dining | $1,355 |
| 4300 W Wilcox St | 3 Beds, 1 Baths | $1,450 |
| 4157 W Adams | 3/1.0 | $2,100 |
Best Neighborhoods to Rent in Near Chicago's Top Employers: A Guide for Renters
A Local Expert's Guide to The 10 Best Chicago Neighborhoods near Major Local Employers. Find your perfect Chicago, IL apartment, condo, or rental home today at ApartmentHomeLiving.com
Read ArticleA Local Expert's Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago
A Local Expert's guide to the Best Student Friendly Neighborhoods Near Colleges in the Chicago, IL metro area for affordable living. Find your perfect Chicago Student apartment, condo, or rental home today at ApartmentHomeliving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #83
Among cities in Illinois for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about 3 Bedroom Madison Square Apartments
What is the largest available 3 Bedroom Madison Square Apartment for rent?
Today's apartment with the most square footage in Madison Square is a 1,150 square feet unit starting from $1,355 at 5100 W Madison.
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
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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.

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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.