5 Bedroom Apartments for Rent in the Southwest Chicago Neighborhood of Chicago, IL (75 Rentals)

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5339 S Maryland Ave
$3,800
Total Monthly Price

Total Monthly Price

Base Rent
$1,900 - $3,800
Total Monthly Price
$1,900 - $3,800
5 Bedroom Apartment Available Jul 15

5339 S Maryland Ave

5339 S Maryland AveChicago, IL 60615
Cost Per Sq.Ft.
  • Smoke Free
property at 6101 W 64th Pl

$16,640

Total Monthly Price

Total Monthly Price

Base Rent
$16,640
Total Monthly Price
$16,640

5 Bedroom, 2 Bath Home for Rent

Available Oct 6

6101 W 64th Pl

ChicagoIL60638

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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3409 W 18th St
5 Bedroom Apartments

3409 W 18th St

3409 W 18th StChicago, IL 60623
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1818 S Hamlin St
5 Bedroom Apartments

1818 S Hamlin St

1818 S Hamlin StChicago, IL 60623
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4712 W Monroe St
5 Bedroom Apartments

4712 W Monroe St

4712 W Monroe StChicago, IL 60644
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5242 W Adams St
5 Bedroom Apartments

5242 W Adams St

5242 W Adams StChicago, IL 60644
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5441 S Union Ave
5 Bedroom Apartments

5441 S Union Ave

5441 S Union AveChicago, IL 60609
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7601 S Essex Ave
5 Bedroom Apartments

7601 S Essex Ave

7601 S Essex AveChicago, IL 60649

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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123 S Peoria St
5 Bedroom Apartments

123 S Peoria St

123 S Peoria StChicago, IL 60607
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Seelos House
5 Bedroom Apartments

Seelos House

1027 E Hyde Park BlvdChicago, IL 60615
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6551 S Ingleside Ave
5 Bedroom Apartments

6551 S Ingleside Ave

6551 S Ingleside AveChicago, IL 60637
Senior Living

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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2038 W 21st St
5 Bedroom Apartments

2038 W 21st St

2038 W 21st StChicago, IL 60608
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4209 W Cermak Rd
5 Bedroom Apartments

4209 W Cermak Rd

4209 W Cermak RdChicago, IL 60623

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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2883 S Throop St
5 Bedroom Apartments

2883 S Throop St

2883 S Throop StChicago, IL 60608
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6915 S Peoria St
5 Bedroom Apartments

6915 S Peoria St

6915 S Peoria StChicago, IL 60621
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1416 E 68th St
5 Bedroom Apartments

1416 E 68th St

1416 E 68th StChicago, IL 60637
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5124 S Michigan Ave
5 Bedroom Apartments

5124 S Michigan Ave

5124 S Michigan AveChicago, IL 60615
  • Utilities Included

Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Looking for a rental near Chicago? These five cities offer excellent options! From small-town charm to excellent business options, you can't go wrong!

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Showing Results 1-50, Page 1 of 2

Southwest Chicago, Chicago, IL Local Guide

Largest Available Southwest Chicago 5 Bedroom Apartments

Apartment ListingModel NameSquare FootagePriced From
Luxury Student Housing at Leavitt Place5 Bedroom 3 Baths1,750 Sq Ft$3,950

Cheapest Available Southwest Chicago 5 Bedroom Apartments

Apartment ListingModel NamePriced From
Luxury Student Housing at Leavitt Place5 Bedroom 3 Baths$3,950

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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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.

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Pet Friendly Lifestyle
Southwest Chicago, Chicago, IL

Ranked #10

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

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Best Local Schools in
Southwest Chicago, Chicago, IL

School data provided by Great Schools

Frequently Asked Questions about Southwest Chicago

How much are Studio apartments in Southwest Chicago?

There are currently 2,556 Studio Apartments in Southwest Chicago with rent ranges from $600 to $9,922 with an average price of $1,866.

What is the current price range for One Bedroom Southwest Chicago Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Southwest Chicago ranges from $700 to $8,957 with an average monthly rent of $2,226.

What does renting a Two Bedroom Apartment in Southwest Chicago cost?

The monthly rent prices of Two Bedroom Apartments currently available in Southwest Chicago range from $500 to $12,074. Today's average rental price for Two Bedrooms here is $2,558.

How expensive are Southwest Chicago Three Bedroom Apartments?

There are currently 1,876 Three Bedroom Apartments listings available in Southwest Chicago on ApartmentHomeLiving.com. The pricing ranges from $989 to $15,952 - averaging $2,746 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

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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.