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$890Studio Apartments Available Now
Washington Plaza
5501 W Washington BlvdChicago, IL 60644
Cheap Apartments for Rent in the Madison Square Neighborhood of Chicago, IL from $700 (50 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
22-26 N Pulaski Rd
ChicagoIL60624
4850 W Adams St
ChicagoIL60644
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$1,0401 Bedroom Apartments Contact Us For Availability
500 S Laramie
500-514 S Laramie AveChicago, IL 60644
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$1,130 - $1,1501 Bedroom Apartments Available Aug 1
330 N Pine
330 N Pine AveChicago, IL 60644
4616 W Jackson Blvd
ChicagoIL60644
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$1,2502 Bedroom Apartments Available Now
4622 W Jackson Blvd, Unit 2
4622 W Jackson BlvdChicago, IL 60644
320 N Pine Ave, Unit 403
320 N Pine Ave
ChicagoIL60644
501 N Central Ave
ChicagoIL60644
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Studio to 1 Bedroom Apartments
Garfield Apartments
4342 W Washington BlvdChicago, IL 60624
Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
Looking for a rental near Chicago? These five cities offer excellent options! From small-town charm to excellent business options, you can't go wrong!
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1 to 3 Bedroom Apartments
La Rose Apartments
5501 W Monroe StChicago, IL 60644
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Studio to 1 Bedroom Apartments
123 N Central Ave
123 N Central AveChicago, IL 60644
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Studio to 1 Bedroom Apartments
5125 W Madison
5125 W Madison StChicago, IL 60644
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1 to 2 Bedroom Apartments
400 S Kilbourn Ave
400 S Kilbourn AveChicago, IL 60624
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Studio to 1 Bedroom Apartments
5001 W Adams
5001 W Adams StChicago, IL 60644
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Studio to 1 Bedroom Apartments
4114 W Washington
4114 W Washington BlvdChicago, IL 60624
24 N Pulaski Rd
ChicagoIL60624
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Studio to 2 Bedroom Apartments
5201 W Washington Blvd (old)
5201 W Washington BlvdChicago, IL 60644
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Studio to 3 Bedroom Apartments
Pine North
542 N Pine AveChicago, IL 60644
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1 to 2 Bedroom Apartments
723 N Central
723-725 N Central AveChicago, IL 60644
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
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1 to 2 Bedroom Apartments
729 N Central
729 N Central AveChicago, IL 60644
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1 to 3 Bedroom Apartments
418 S Laramie
418-424 S Laramie AveChicago, IL 60644
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1 to 3 Bedroom Apartments
600-602 N Lorel Ave
600-602 N Lorel AveChicago, 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 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 to 4 Bedroom Apartments
5101 W Monroe
5101-5103 W Monroe StChicago, IL 60644
209 N Kolmar Ave
ChicagoIL60624
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1 to 2 Bedroom Apartments
5011 W Maypole
5011-5015 W Maypole AveChicago, IL 60644
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1 to 3 Bedroom Apartments
5024 W Quincy
5024-5028 W Quincy StChicago, IL 60644
Chicago Relocation 101: Mastering Utilities, Registration, and the CTA
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.
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Studio to 3 Bedroom Apartments
1115 S Karlov
1115 S Karlov AveChicago, IL 60624
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2 to 3 Bedroom Apartments
Pangea Apartments
5448 W Adams StChicago, IL 60644
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1 to 4 Bedroom Apartments
4815 W Monroe St
4815 W Monroe StChicago, IL 60644
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2 to 3 Bedroom Apartments
701 N Lotus Ave
701 N Lotus AveChicago, 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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1 Bedroom Apartments
5012 W Jackson Blvd
5012 W Jackson BlvdChicago, IL 60644
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Studio to 2 Bedroom Apartments
Jade Apartments
1-15 N Keeler AveChicago, IL 60624
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2 to 3 Bedroom Apartments
400 S Laramie
400 S Laramie AveChicago, IL 60644
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1 to 2 Bedroom Apartments
5328 W Harrison
5328 W Harrison StChicago, IL 60644
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1 Bedroom Apartments
5015 W Jackson
5015 W Jackson BlvdChicago, 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!
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2 to 3 Bedroom Apartments
708 S Karlov
708-14 S Karlov AveChicago, IL 60624
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1 to 2 Bedroom Apartments
4641 W Jackson Blvd
4641 W Jackson BlvdChicago, IL 60644
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1 to 2 Bedroom Apartments
5500 W Van Buren
5500 W Van Buren StChicago, IL 60644
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2 to 3 Bedroom Apartments
4443 W Gladys Ave
4443 W Gladys AveChicago, IL 60624
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1 to 3 Bedroom Apartments
5314 W Washington
5201-5207 W Washington BlvdChicago, 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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2 to 3 Bedroom Apartments
5036 W Quincy St
5036 W Quincy StChicago, IL 60644
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Studio to 3 Bedroom Apartments
109 N Laramie Ave
109 N Laramie AveChicago, IL 60644
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2 to 3 Bedroom Apartments
4814 W Monroe St
4814 W Monroe StChicago, IL 60644
5145 W Ferdinand St
ChicagoIL60644
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
Showing Results 1-50, Page 1 of 1
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 50 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
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Madison Square Apartments for Rent
The cheapest available apartment rental in the Madison Square area of Chicago, IL is a Studio unit found at Washington Plaza priced from $890. Pine North has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,050. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Washington Plaza | Studio Apartment | Studio,1BA | $890 |
| Pine North | 1BR/1.0BA | 1BR,1BA | $1,050 |
| 723 N Central | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,055 |
| 418 S Laramie | 1 Bedroom 1 Bath Apartment with Dining | 1BR,1BA | $1,090 |
| 5024 W Quincy | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,155 |
| 1115 S Karlov | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,175 |
| 708 S Karlov | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1,230 |
| 5100 W Madison | 3 Bedroom 2 Bath Apartment with Dining | 3BR,2BA | $1,355 |
| 4300 W Wilcox St | 3 Beds, 1 Baths | 3BR,1BA | $1,450 |
Best Value Apartments for Rent in Madison Square, IL
As of July 26, 2026 the best value apartment in the Madison Square area is the $1.18 price per square foot 3 Bedroom 2 Bath Apartment with Dining Model at 5100 W Madison in the in the Austin neighborhood starting from $1,355. The second greatest value Madison Square apartment is the 2/1.0 Model at 200 N Kenneth starting at $1,550 with a $1.55 price per square foot in the West Garfield Park neighborhood. Here is today’s list of the best values for Madison Square apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 5100 W Madison | 3 Bedroom 2 Bath Apartment with Dining | 3BR,2BA | $1.18 |
| 200 N Kenneth | 2/1.0 | 2BR,1BA | $1.55 |
| 4023 W Carroll Ave, Unit 2 | 4023 W Carroll Ave | 4BR,2BA | $1.80 |
| 4318 W Monroe St, Unit 1st floor | 4318 W Monroe St | 2BR,1BA | $1.67 |
| 5005 W Ferdinand St, Unit 5007 w unit #1 | 5005 W Ferdinand St | 2BR,1BA | $1.88 |
| 5024 W Quincy | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.65 |
| 723 N Central | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.56 |
| Pine North | 1BR/1.0BA | 1BR,1BA | $1.64 |
| 708 S Karlov | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.92 |
| 418 S Laramie | 1 Bedroom 1 Bath Apartment with Dining | 1BR,1BA | $1.86 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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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.
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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 Cheap Madison Square Apartments
What is the lowest price for a Cheap Two Bedroom Madison Square Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Madison Square is starting from $1,200 at Pine North.
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
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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.
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Rent According to Income: A Look at Income-Restricted Rentals
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The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
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.
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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.