Apartments for Rent in the Madison Square Neighborhood of Chicago, IL Under $2,000 (91 Rentals)

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217 N Laramie Ave, Unit 1
$1,895
Total Monthly Price

Total Monthly Price

Base Rent
$1,895
Total Monthly Price
$1,895
5 Bedroom Apartment Available Now

217 N Laramie Ave, Unit 1

217 N Laramie AveChicago, IL 60644
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5078 W Adams St, Unit 1
$1,800
Total Monthly Price

Total Monthly Price

Base Rent
$1,800
Total Monthly Price
$1,800
3 Bedroom Apartment Available Now

5078 W Adams St, Unit 1

5078 W Adams StChicago, IL 60644
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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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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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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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4443 W Gladys Ave
2 to 3 Bedroom Apartments

4443 W Gladys Ave

4443 W Gladys 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

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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5236 W Harrison
1 to 3 Bedroom Apartments

5236 W Harrison

5236 W HarrisonChicago, IL 60644
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701 S Karlov Ave
Studio to 3 Bedroom Apartments

701 S Karlov Ave

701 S Karlov AveChicago, IL 60624
  • Utilities Included
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1115 S Karlov Ave
Studio to 3 Bedroom Apartments

1115 S Karlov Ave

1115 S Karlov AveChicago, IL 60624
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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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423 N Central Ave
1 to 3 Bedroom Apartments

423 N Central Ave

423 N Central AveChicago, IL 60644
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5556-5576 W Jackson Blvd
2 to 4 Bedroom Apartments

5556-5576 W Jackson Blvd

5556-5576 W Jackson BlvdChicago, 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

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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Madison Square, Chicago, IL Local Guide

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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Pet Friendly Lifestyle
Madison Square, Chicago, IL

Ranked #92

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

How much are Studio apartments in Madison Square?

There are currently 67 Studio Apartments in Madison Square with rent ranges from $890 to $890 with an average price of $890.

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 $1,095 to $9,364. Today's average rental price for Two Bedrooms here is $2,496.

How expensive are Madison Square Three Bedroom Apartments?

There are currently 122 Three Bedroom Apartments listings available in Madison Square on ApartmentHomeLiving.com. The pricing ranges from $1,700 to $2,400 - averaging $2,028 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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A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago

Written by: Nicole Harms

I’m Nicole, your ApartmentHomeLiving.com Local Expert for Chicago, IL. As a resident of the Chicago area for over 20 years, I’ve learned which neighborhoods are great and which are best avoided.

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Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago

Written by: Nicole Harms

With world-class museums lining its streets, Chicago is a place people go to learn. It’s not surprising, therefore, that it’s also home to multiple colleges and universities with national and global reputations.

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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.

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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

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

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.

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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.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.