4 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (31 Rentals)

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Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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721 S Karlov Ave
4 Bedroom Apartments

721 S Karlov Ave

721 S Karlov AveChicago, IL 60624
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4134 W Wilcox St
4 Bedroom Apartments

4134 W Wilcox St

4134 W Wilcox StChicago, IL 60624
  • Utilities Included

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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4042 W Wilcox St
4 Bedroom Apartments

4042 W Wilcox St

4042 W Wilcox StChicago, IL 60624
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4712 W Monroe St
4, 5 Bedroom Apartments

4712 W Monroe St

4712 W Monroe StChicago, IL 60644

Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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654 N Pine Ave
4 Bedroom Apartments

654 N Pine Ave

654 N Pine AveChicago, IL 60644
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Washington Court
4 Bedroom Apartments

Washington Court

5424 W Washington BlvdChicago, IL 60644
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Washington Lotus
4 Bedroom Apartments

Washington Lotus

5417-5429 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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4815 W Monroe St
4 Bedroom Apartments

4815 W Monroe St

4815 W Monroe StChicago, IL 60644
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Austin Apartments
4 Bedroom Apartments

Austin Apartments

5101-5103 W Monroe StChicago, IL 60644
Showing Results 1-31, Page 1 of 1

Madison Square, Chicago, IL Local Guide

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

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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

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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 #88

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

Pet Friendliness Lifestyle Score

3.0
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.