2 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (199 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
close
View Me
238 N Lockwood Ave
$1,500
Total Monthly Price

Total Monthly Price

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

238 N Lockwood Ave

238 N Lockwood AveChicago, IL 60644
Affordability
  • Smoke Free

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.

Read Article
close
View Me
5302 W Ohio St
2 Bedroom Apartments

5302 W Ohio St

5302 W Ohio StChicago, IL 60644
  • Utilities Included
  • Smoke Free

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!

Read Article
close
View Me
4345 W Wilcox St
2 Bedroom Apartments

4345 W Wilcox St

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

4101 W Gladys

4101 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.

Read Article
close
View Me
4205 W Gladys
2 Bedroom Apartments

4205 W Gladys

4205 W GladysChicago, IL 60624
close
View Me
HICA Redevelopment
2 Bedroom Apartments

HICA Redevelopment

5042 W Washington BlvdChicago, IL 60644
  • Smoke Free

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.

Read Article
close
View Me
131 N Pine Ave
2 Bedroom Apartments

131 N Pine Ave

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

726 N Pine Ave

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

163 N Lamon Ave

163 N Lamon AveChicago, IL 60644
close
View Me
4134 W Wilcox St
2 Bedroom Apartments

4134 W Wilcox St

4134 W Wilcox StChicago, IL 60624
  • Utilities Included
close
View Me
Pine Race
2 Bedroom Apartments

Pine Race

557-563 N Pine 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.

Read Article
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 5567 W Van Buren St and is listed at 2,875 square feet priced from $1,900. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
5567 W Van Buren St2Bd/1B - w/ an office2,875 Sq Ft$1,900
708-14 S Karlov Ave 4101-05 W Fifth Avenue Chicago, IL 606242 Bedroom 1 Bath Apartment1,100 Sq Ft$1,230
200 N Kenneth2/1.01,000 Sq Ft$1,300
400-08 S Laramie Ave Chicago, IL 606442 Bedroom 1 Bath Apartment951 Sq Ft$1,265
4152 W Lake St2/1.0900 Sq Ft$1,200
5328 W Harrison St Chicago, IL 606442 Bedroom 1 Bath Apartment861 Sq Ft$1,235
729 N Central Chicago, IL 606442 Bedroom 1 Bath Garden675 Sq Ft$1,270
5314 W Washington Blvd Chicago, IL 606442 Bedroom 1 Bath Apartment660 Sq Ft$1,295
5036-38 W Quincy St Chicago, IL 606442 Bedroom 1 Bath Apartment650 Sq Ft$1,325
5556-64 W Jackson Blvd Chicago, IL 606442 Bedroom 1 Bath Garden646 Sq Ft$1,210

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 Garden Model starting from $1,107 at 5040-42 W Quincy St Chicago, IL 60644. The average price for all 2 Bedroom apartments in Madison Square is currently $1,418. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
5040-42 W Quincy St Chicago, IL 606442 Bedroom 1 Bath Garden$1,107
5500 W Van Buren St Chicago, IL 606442 Bedroom 1 Bath Apartment$1,155
5328 W Harrison St Chicago, IL 606442 Bedroom 1 Bath Garden$1,190
4152 W Lake St2/1.0$1,200
5556-64 W Jackson Blvd Chicago, IL 606442 Bedroom 1 Bath Garden$1,210
400-402 S Kilbourn Ave Chicago, IL 606242 Bedroom 1 Bath Apartment$1,230
708-14 S Karlov Ave 4101-05 W Fifth Avenue Chicago, IL 606242 Bedroom 1 Bath Apartment$1,230
400-08 S Laramie Ave Chicago, IL 606442 Bedroom 1 Bath Apartment$1,265
729 N Central Chicago, IL 606442 Bedroom 1 Bath Garden$1,270
5314 W Washington Blvd Chicago, IL 606442 Bedroom 1 Bath Apartment$1,295

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.

Read Article
Decorative image

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

Read Article
Decorative image

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.

Read Article
Decorative image

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.

Read Article
Decorative image

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

Read Article
Decorative image

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.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Madison Square, Chicago, IL

Ranked #111

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

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

decorative image of woman handing cat to small boy

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 5040-42 W Quincy St Chicago, IL 60644 listed at $1,107.

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 $1,418.

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 2,875 square feet unit starting from $1,900 at 5567 W Van Buren St.

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 1,032 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

decorative image for A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago article

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.

decorative image for Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago article

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.

decorative image for Best Neighborhoods to Rent in Near Chicago's Top Employers article

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.

decorative image for Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago article

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 Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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

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.