2 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (190 Rentals)

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La Rose Apartments
2 Bedroom Apartments

La Rose Apartments

5501 W Monroe StChicago, IL 60644
  • Utilities Included

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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602 N Lorel Ave
2 Bedroom Apartments

602 N Lorel Ave

600-602 N Lorel AveChicago, IL 60644
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Pine North
2 Bedroom Apartments

Pine North

542 N Pine AveChicago, IL 60644
  • Utilities Included
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701 S Karlov Ave
2 Bedroom Apartments

701 S Karlov Ave

701 S Karlov AveChicago, IL 60624
  • Utilities Included
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200 N Kenneth
2 Bedroom Apartments

200 N Kenneth

200 N Kenneth AveChicago, IL 60624
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5328 W Harrison
2 Bedroom Apartments

5328 W Harrison

5328 W Harrison StChicago, IL 60644
  • Utilities Included
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5236 W Harrison
2 Bedroom Apartments

5236 W Harrison

5236 W HarrisonChicago, IL 60644
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400-02 S Kilbourn Ave
2 Bedroom Apartments

400-02 S Kilbourn Ave

400 S Kilbourn AveChicago, IL 60624
  • Utilities Included
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5500 W Van Buren
2 Bedroom Apartments

5500 W Van Buren

5500 W Van Buren StChicago, IL 60644
  • 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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634-640 N Lamon
2 Bedroom Apartments

634-640 N Lamon

634 N Lamon AveChicago, IL 60644
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729 N Central
2 Bedroom Apartments

729 N Central

729 N Central AveChicago, IL 60644
  • Utilities Included
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4152 W Lake St
2 Bedroom Apartments

4152 W Lake St

4152-4156 W Lake StChicago, IL 60624
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617 N Central Ave
2 Bedroom Apartments

617 N Central Ave

617-619 N Central AveChicago, IL 60644
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148 N La Crosse Ave
2 Bedroom Apartments

148 N La Crosse Ave

148 N La Crosse AveChicago, IL 60644
  • Utilities Included
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5556-64 W Jackson Blvd
2 Bedroom Apartments

5556-64 W Jackson Blvd

5556-5576 W Jackson BlvdChicago, IL 60644
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5302 W Ohio St
2 Bedroom Apartments

5302 W Ohio St

5302 W Ohio StChicago, IL 60644
  • Utilities Included
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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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Jade Apartments
2 Bedroom Apartments

Jade Apartments

1-15 N Keeler AveChicago, IL 60624
  • Utilities Included
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127 Central
2 Bedroom Apartments

127 Central

127 N Central AveChicago, IL 60644
  • Utilities Included
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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

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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4747 W Fulton St
2 Bedroom Apartments

4747 W Fulton St

4747 W Fulton StChicago, IL 60644
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Pine Race
2 Bedroom Apartments

Pine Race

557-563 N Pine AveChicago, IL 60644
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701 N Lotus Ave
2 Bedroom Apartments

701 N Lotus Ave

701 N Lotus AveChicago, IL 60644
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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

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.

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 708-14 S Karlov Ave and is listed at 1,100 square feet priced from $1,415. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
708-14 S Karlov Ave2 Bedroom 1 Bath Apartment1,100 Sq Ft$1,415
200 N Kenneth2BR/1.0BA1,000 Sq Ft$1,175
5236 W Harrison2 Bedroom 1 Bath Apartment750 Sq Ft$1,185
Pine North2BR/1.0BA750 Sq Ft$1,150
729 N Central2 Bedroom 1 Bath Apartment725 Sq Ft$1,250
4641-43 W Jackson Blvd2 Bedroom 1 Bath Apartment681 Sq Ft$1,230

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 $1,150 at Pine North. The average price for all 2 Bedroom apartments in Madison Square is currently $1,312. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
Pine North2BR/1.0BA$1,150
200 N Kenneth2BR/1.0BA$1,175
5236 W Harrison2 Bedroom 1 Bath Apartment$1,185
4641-43 W Jackson Blvd2 Bedroom 1 Bath Apartment$1,230
729 N Central2 Bedroom 1 Bath Apartment$1,250
708-14 S Karlov Ave2 Bedroom 1 Bath Apartment$1,415

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Pet Friendly Lifestyle
Madison Square, Chicago, IL

Ranked #136

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 Pine North listed at $1,150.

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 $1,312.

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 $1,415 at 708-14 S Karlov 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 0 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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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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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.