Apartments for Rent in the Madison Square Neighborhood of Chicago, IL Under $2,000 (80 Rentals)

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5143 W Washington Blvd, Unit 2
$1,800

Total Monthly Price

Base Rent$1,800
Total Monthly Price$1,800
4 Bedroom Apartment Available Oct 1

5143 W Washington Blvd, Unit 2

5143 W Washington BlvdChicago, IL 60644
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4710 W Jackson Blvd, Unit 2
$1,500

Total Monthly Price

Base Rent$1,500
Total Monthly Price$1,500
2 Bedroom Apartment Available Now

4710 W Jackson Blvd, Unit 2

4710 W Jackson BlvdChicago, IL 60644
Cost Per Sq.Ft.
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property at 646 N Long Ave
$2,000

Total Monthly Price

Base Rent$2,000
Total Monthly Price$2,000
3 Bedroom, 1.5 Bath Townhome for Rent
Available Now
Affordability

646 N Long Ave

ChicagoIL60644

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.

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property at 4940 W Van Buren St
$1,900 - $2,300
3 To 4 Bedroom Rentals
Available Now
Affordability

4940 W Van Buren 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.

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4443 W Gladys Ave
2 to 3 Bedroom Apartments

4443 W Gladys Ave

4443 W Gladys AveChicago, 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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W. Washington
1 to 3 Bedroom Apartments

W. Washington

5027-5029 W Washington BlvdChicago, IL 60644
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4300 W Wilcox St
1 to 3 Bedroom Apartments

4300 W Wilcox St

4300 W Wilcox StChicago, IL 60624
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Pine St 316-318
2 Bedroom Apartments

Pine St 316-318

312-318 N Pine AveChicago, IL 60644
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708 S Karlov
2 to 3 Bedroom Apartments

708 S Karlov

708-14 S Karlov AveChicago, IL 60624
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16-18 N Lorel Ave
1 to 3 Bedroom Apartments

16-18 N Lorel Ave

16-18 N Lorel AveChicago, IL 60644
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654 N Pine
Studio to 4 Bedroom Apartments

654 N Pine

654 N Pine AveChicago, IL 60644
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200 N Kenneth
1 to 3 Bedroom Apartments

200 N Kenneth

200 N Kenneth AveChicago, IL 60624
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5556 W Jackson
2 to 4 Bedroom Apartments

5556 W Jackson

5556-5576 W Jackson BlvdChicago, IL 60644
  • Utilities Included
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4653 W Jackson Blvd
1 to 3 Bedroom Apartments

4653 W Jackson Blvd

4653-4659 W Jackson BlvdChicago, IL 60644
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423 N Central
1 to 3 Bedroom Apartments

423 N Central

423 N Central AveChicago, 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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701 N Lotus
2 to 3 Bedroom Apartments

701 N Lotus

701 N Lotus AveChicago, IL 60644
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5236 W Harrison
1 to 3 Bedroom Apartments

5236 W Harrison

5236 W HarrisonChicago, IL 60644
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4725 W maypole
1 to 5 Bedroom Apartments

4725 W maypole

4721-4725 W Maypole AveChicago, IL 60644
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148 N La Crosse
2 to 3 Bedroom Apartments

148 N La Crosse

148 N La Crosse AveChicago, IL 60644
  • Utilities Included
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5036 W Quincy St
2 to 3 Bedroom Apartments

5036 W Quincy St

5036 W Quincy StChicago, IL 60644
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4814 W Monroe St
2 to 3 Bedroom Apartments

4814 W Monroe St

4814 W Monroe StChicago, IL 60644
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109 N Laramie Ave
Studio to 3 Bedroom Apartments

109 N Laramie Ave

109 N Laramie AveChicago, IL 60644
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5314 W Washington
1 to 3 Bedroom Apartments

5314 W Washington

5201-5207 W Washington BlvdChicago, IL 60644
  • Utilities Included

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Showing Results 1-50, Page 1 of 2

Madison Square, Chicago, IL Local Guide

Navigating 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.

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A 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

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Real 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.

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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.

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Pet Friendly Lifestyle
Madison Square, Chicago, IL

Ranked #89

Among cities in Illinois for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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Frequently Asked Questions about Madison Square

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 $1,000 to $1,200 with an average monthly rent of $1,100.

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 $1,100 to $9,739. Today's average rental price for Two Bedrooms here is $2,149.

How expensive are Madison Square Three Bedroom Apartments?

There are currently 124 Three Bedroom Apartments listings available in Madison Square on ApartmentHomeLiving.com. The pricing ranges from $1,280 to $2,600 - averaging $1,761 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

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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.

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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.

decorative image for Chicago Relocation 101: Mastering Utilities, Registration, and the CTA article

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.

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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

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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.

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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.

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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.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.