2 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (198 Rentals)

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property at 220 N Laporte Ave

$9,364

Total Monthly Price

Total Monthly Price

Base Rent
$9,364
Total Monthly Price
$9,364

2 Bedroom, 1 Bath Home for Rent

Available Now

220 N Laporte Ave

ChicagoIL60644

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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4345 W Wilcox St
2 Bedroom Apartments

4345 W Wilcox St

4345 W Wilcox StChicago, IL 60624
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4101 W Gladys
2 Bedroom Apartments

4101 W Gladys

4101 W GladysChicago, IL 60624

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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4205 W Gladys
2 Bedroom Apartments

4205 W Gladys

4205 W GladysChicago, IL 60624

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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HICA Redevelopment
2 Bedroom Apartments

HICA Redevelopment

5042 W Washington BlvdChicago, IL 60644
  • Smoke Free
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Pine Race
2 Bedroom Apartments

Pine Race

557-563 N Pine AveChicago, 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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4134 W Wilcox St
2 Bedroom Apartments

4134 W Wilcox St

4134 W Wilcox StChicago, IL 60624
  • Utilities Included
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131 N Pine Ave
2 Bedroom Apartments

131 N Pine Ave

131 N Pine AveChicago, IL 60644
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726 N Pine Ave
2 Bedroom Apartments

726 N Pine Ave

726 N Pine AveChicago, IL 60644
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163 N Lamon Ave
2 Bedroom Apartments

163 N Lamon Ave

163 N Lamon AveChicago, IL 60644
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4832 W Monroe St
2 Bedroom Apartments

4832 W Monroe St

4832 W Monroe StChicago, IL 60644

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 4

Madison Square, Chicago, IL Local Guide

Largest Available Madison Square 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in the Madison Square area of Chicago, IL is found at 200 N Kenneth Ave and is listed at 1,000 square feet priced from $1,300. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
200 N Kenneth Ave2/1.01,000 Sq Ft$1,300
109 N Laramie Ave2 Bedroom 1 Bath Apartment850 Sq Ft$1,295
400 S Kilbourn Ave2 Bedroom 1 Bath Apartment631 Sq Ft$1,170
Congress Commons2 Bedroom 1 Bath Apartment550 Sq Ft$1,095
5500 W Van Buren St2 Bedroom 1 Bath Apartment496 Sq Ft$1,155

Cheapest Available Madison Square 2 Bedroom Apartments

Currently the lowest priced 2 Bedroom apartment unit Madison Square of Chicago, IL is the 2 Bedroom 1 Bath Apartment Model starting from $1,095 at Congress Commons. The average price for all 2 Bedroom apartments in Madison Square is currently $1,500. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
Congress Commons2 Bedroom 1 Bath Apartment$1,095
5500 W Van Buren St2 Bedroom 1 Bath Apartment$1,155
400 S Kilbourn Ave2 Bedroom 1 Bath Apartment$1,170
109 N Laramie Ave2 Bedroom 1 Bath Apartment$1,295
200 N Kenneth Ave2/1.0$1,300

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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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 #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 2 Bedroom Madison Square Apartments

What is the Cheapest apartment in Madison Square with 2 Bedroom?

Currently the most affordable 2 Bedroom in Madison Square is at Congress Commons listed at $1,095.

What is the largest available 2 Bedroom Madison Square Apartment for rent?

Today's apartment with the most square footage in Madison Square is a 1,000 square feet unit starting from $1,300 at 200 N Kenneth Ave.

What is the average size for Madison Square 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Madison Square is currently 875 sq ft.

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.