2 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (194 Rentals)

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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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5302 W Ohio St
2 Bedroom Apartments

5302 W Ohio St

5302 W Ohio StChicago, IL 60644
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4345 W Wilcox St
2 Bedroom Apartments

4345 W Wilcox St

4345 W Wilcox StChicago, IL 60624

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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4101 W Gladys
2 Bedroom Apartments

4101 W Gladys

4101 W GladysChicago, IL 60624
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4205 W Gladys
2 Bedroom Apartments

4205 W Gladys

4205 W GladysChicago, IL 60624

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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HICA Redevelopment
2 Bedroom Apartments

HICA Redevelopment

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

Pine Race

557-563 N Pine AveChicago, IL 60644

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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4134 W Wilcox St
2 Bedroom Apartments

4134 W Wilcox St

4134 W Wilcox StChicago, IL 60624
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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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4832 W Monroe St
2 Bedroom Apartments

4832 W Monroe St

4832 W Monroe StChicago, IL 60644
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4747 W Fulton St
2 Bedroom Apartments

4747 W Fulton St

4747 W Fulton StChicago, 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

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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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 5223-5225 W Washington Blvd and is listed at 1,100 square feet priced from $1,450. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
5223-5225 W Washington Blvd2 Bed 1 Bath1,100 Sq Ft$1,450
4814-4820 W Monroe St Chicago, IL 606442 Bedroom 1 Bath Garden961 Sq Ft$1,305
4152 W Lake St2/1.0900 Sq Ft$1,250
634-640 N Lamon2/1.0800 Sq Ft$1,250
723-25 N Central Ave Chicago, IL 606442 Bedroom 2 Bath Apartment750 Sq Ft$1,175
Pine North2BR/1.0BA750 Sq Ft$1,100
400-08 S Laramie Ave Chicago, IL 606442 Bedroom 1 Bath Apartment741 Sq Ft$1,220
729 N Central Chicago, IL 606442 Bedroom 1 Bath Apartment725 Sq Ft$1,245

Cheapest Available Madison Square 2 Bedroom Apartments

Currently the lowest priced 2 Bedroom apartment unit Madison Square of Chicago, IL is the 2BR/1.0BA Model starting from $1,100 at Pine North. The average price for all 2 Bedroom apartments in Madison Square is currently $3,341. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
Pine North2BR/1.0BA$1,100
723-25 N Central Ave Chicago, IL 606442 Bedroom 2 Bath Apartment$1,175
400-08 S Laramie Ave Chicago, IL 606442 Bedroom 1 Bath Apartment$1,220
708-14 S Karlov Ave 4101-05 W Fifth Avenue Chicago, IL 606242 Bedroom 1 Bath Apartment$1,230
729 N Central Chicago, IL 606442 Bedroom 1 Bath Apartment$1,245
634-640 N Lamon2/1.0$1,250
4152 W Lake St2/1.0$1,250
5556-64 W Jackson Blvd Chicago, IL 606442 Bedroom 1 Bath Apartment$1,260
4814-4820 W Monroe St Chicago, IL 606442 Bedroom 1 Bath Garden$1,305
5036-38 W Quincy St Chicago, IL 606442 Bedroom 1 Bath Apartment$1,325

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.

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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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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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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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 #146

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

How much is the average rent for a 2 Bedroom Madison Square Apartment?

The average rent for a 2 Bedroom Apartment in Madison Square is $3,341.

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 1,100 square feet unit starting from $1,450 at 5223-5225 W Washington Blvd.

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 1,140 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

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!