close
View Me
$890 - $1,100Studio to 1 Bedroom 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 (49 Rentals)
Search the lowest-cost Apartments available for rent right now in the Madison Square area of Chicago.
close
View Me
$1,0001 Bedroom Apartments Available Now
567 N Pine Ave
567 N Pine AveChicago, IL 60644
close
View Me
$1,100 - $1,2802 to 3 Bedroom Apartments Available Sep 16
500 S Laramie
500-514 S Laramie AveChicago, IL 60644
close
View Me
$1,2001 Bedroom Apartments Available Now
4616 W Jackson Blvd, Unit 4616 w Jackson Garden
4616 W Jackson BlvdChicago, IL 60644
close
View Me
$1,205 - $1,2202 Bedroom Apartments Available Now
400 S Laramie
400 S Laramie AveChicago, IL 60644
close
View Me
$1,2502 Bedroom Apartments Available Now
4622 W Jackson Blvd, Unit 3
4622 W Jackson BlvdChicago, IL 60644
320 N Pine Ave, Unit 403
320 N Pine Ave
ChicagoIL60644
5309 W Gladys Ave
ChicagoIL60644
4035 W Gladys Ave, Unit 2N
4035 W Gladys Ave
ChicagoIL60624
The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Chicago may cost more than the national average, but with the right neighborhood, a smart transit strategy, and a few local insider tips, living well in the Windy City is more achievable than you might think. Our local expert breaks down everything from rent and groceries to transportation and healthcare so you can plan your move with confidence.
close
View Me
Studio to 1 Bedroom Apartments
Garfield Apartments
4342 W Washington BlvdChicago, IL 60624
close
View Me
1 to 3 Bedroom Apartments
La Rose Apartments
5501 W Monroe StChicago, IL 60644
close
View Me
Studio to 3 Bedroom Apartments
701 S Karlov
701 S Karlov AveChicago, IL 60624
close
View Me
Studio to 1 Bedroom Apartments
4114 W Washington
4114 W Washington BlvdChicago, IL 60624
close
View Me
Studio to 1 Bedroom Apartments
123 N Central Ave
123 N Central AveChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
5125 W Madison
5125 W Madison StChicago, IL 60644
close
View Me
Studio to 1 Bedroom Apartments
5001 W Adams
5001 W Adams StChicago, IL 60644
close
View Me
Studio to 4 Bedroom Apartments
330 N Pine
330 N Pine AveChicago, IL 60644
close
View Me
Studio to 2 Bedroom Apartments
5201 W Washington Blvd (old)
5201 W Washington BlvdChicago, 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.
728 N Pine Ave
ChicagoIL60644
close
View Me
1 to 2 Bedroom Apartments
723 N Central
723-725 N Central AveChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
729 N Central
729 N Central AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
600-602 N Lorel Ave
600-602 N Lorel AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5100 W Madison
5100-5104 W Madison StChicago, IL 60644
close
View Me
1 Bedroom Apartments
5018 W Jackson
5018 W Jackson BlvdChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
5011 W Maypole
5011-5015 W Maypole AveChicago, IL 60644
close
View Me
Studio to 2 Bedroom Apartments
Pine North
542 N Pine AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5040 W Quincy St
5040 W Quincy StChicago, IL 60644
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!
close
View Me
1 to 4 Bedroom Apartments
5101 W Monroe
5101-5103 W Monroe StChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
5328 W Harrison
5328 W Harrison StChicago, IL 60644
close
View Me
1 to 4 Bedroom Apartments
4815 W Monroe
4815 W Monroe StChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
400 S Kilbourn Ave
400 S Kilbourn AveChicago, IL 60624
close
View Me
Studio to 3 Bedroom Apartments
1115 S Karlov
1115 S Karlov AveChicago, IL 60624
close
View Me
2 to 3 Bedroom Apartments
Pangea Apartments
5448 W Adams StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5100 W Monroe
5100-5104 W Monroe StChicago, IL 60644
close
View Me
1 Bedroom Apartments
5012 W Jackson Blvd
5012 W Jackson BlvdChicago, IL 60644
close
View Me
Studio to 2 Bedroom Apartments
Jade Apartments
1-15 N Keeler AveChicago, IL 60624
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.
close
View Me
1 to 3 Bedroom Apartments
5024 W Quincy
5024-5028 W Quincy StChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
418 S Laramie
418-424 S Laramie AveChicago, IL 60644
close
View Me
1 Bedroom Apartments
5015 W Jackson
5015 W Jackson BlvdChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
708 S Karlov
708-14 S Karlov AveChicago, IL 60624
close
View Me
1 to 2 Bedroom Apartments
4641 W Jackson Blvd
4641 W Jackson BlvdChicago, IL 60644
close
View Me
1 to 2 Bedroom Apartments
5500 W Van Buren
5500 W Van Buren StChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
4443 W Gladys Ave
4443 W Gladys AveChicago, IL 60624
close
View Me
2 Bedroom Apartments
Pine St 316-318
312-318 N Pine AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
5314 W Washington
5201-5207 W Washington BlvdChicago, IL 60644
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.
close
View Me
Studio to 3 Bedroom Apartments
109 N Laramie Ave
109 N Laramie AveChicago, IL 60644
close
View Me
1 to 3 Bedroom Apartments
4300 W Wilcox St
4300 W Wilcox StChicago, IL 60624
close
View Me
2 to 3 Bedroom Apartments
4814 W Monroe St
4814 W Monroe StChicago, IL 60644
close
View Me
2 to 3 Bedroom Apartments
5036 W Quincy St
5036 W Quincy StChicago, IL 60644
Showing Results 1-49, 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 | $1,100 | $1,000 | $1,200 |
| Madison Square 2 Bedroom Apartments | $2,149 | $1,100 | $9,739 |
| Madison Square 3 Bedroom Apartments | $1,761 | $1,280 | $2,600 |
| Madison Square 4 Bedroom Apartments | $1,933 | $1,800 | $2,200 |
Browse Apartments in this Neighborhood
There are currently 49 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
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 5001 W Adams priced from $960. 567 N Pine Ave has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,000. Here are the most affordable Madison Square apartments for rent in Chicago, IL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 5001 W Adams | Studio Apartment | Studio,1BA | $960 |
| 567 N Pine Ave | 2B | 1BR,1BA | $1,000 |
| 723 N Central | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,055 |
| Washington Plaza | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,100 |
| Pine North | 1BR/1.0BA | 1BR,1BA | $1,125 |
| 5018 W Jackson | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,125 |
| 5101 W Monroe | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,140 |
| 330 N Pine | 1 Bedroom 1 Bath Apartment with Dining | 1BR,1BA | $1,150 |
| 5024 W Quincy | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1,200 |
| 418 S Laramie | 2 Bedroom 1 Bath Apartment with Dining | 2BR,1BA | $1,205 |
Best Value Apartments for Rent in Madison Square, IL
As of September 09, 2026 the best value apartment in the Madison Square area is the $1.20 price per square foot 4 Bedroom 1.5 Bath Apartment Model at 654 N Pine in the in the Austin neighborhood starting from $1,925. The second greatest value Madison Square apartment is the 4710 W Jackson Blvd Model at 4710 W Jackson Blvd, Unit 2 starting at $1,500 with a $1.14 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. |
|---|---|---|---|
| 654 N Pine | 4 Bedroom 1.5 Bath Apartment | 4BR,1.5BA | $1.20 |
| 4710 W Jackson Blvd, Unit 2 | 4710 W Jackson Blvd | 2BR,1BA | $1.14 |
| 5100 W Madison | 3 Bedroom 2 Bath Apartment with Dining | 3BR,2BA | $1.18 |
| 5223-5225 W Washington Blvd | 2 Bed 1 Bath | 2BR,1BA | $1.36 |
| 200 N Kenneth | 2/1.0 | 2BR,1BA | $1.65 |
| Pine St 316-318 | 2BR/1.0BA | 2BR,1BA | $1.39 |
| 400 S Laramie | 2 Bedroom 1 Bath Apartment | 2BR,1BA | $1.50 |
| 418 S Laramie | 2 Bedroom 1 Bath Apartment with Dining | 2BR,1BA | $1.59 |
| 567 N Pine Ave | 2B | 1BR,1BA | $1.43 |
| 723 N Central | 1 Bedroom 1 Bath Apartment | 1BR,1BA | $1.56 |
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.
Read Article
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 ArticleNavigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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 Article
Quick 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.
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
Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #89
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
How much is rent for a Cheap One Bedroom Madison Square Apartment?
The lowest price for a Cheap One Bedroom Madison Square Apartment is $1,000 at 567 N Pine Ave.
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.
What is the most affordable Madison Square Three Bedroom Apartment?
The best deal on a cheap Madison Square Three Bedroom Apartment rental is at 4300 W Wilcox St and starts from $1,350.
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
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
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.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
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.