
Apartments near Winchester Plaza in Chicago, IL (3,919 Rentals)


4045 N Sawyer Ave

6726 N Sheridan Rd

1307 W Addison St

6509-6513 N Sacramento Ave

849 GRACE

3929 N Pine Grove Ave

853 W Grace St

1200 W Addison St

Viridian on Sheridan

1029-1051 W NorthShore Ave

3708-3714 N Sheffield Ave

Oso Apartments

The Court

6542 N Richmond Ave

Gill Park Cooperative

668 W Sheridan Rd

835 W Grace St

1063 W. Columbia

Reside 707

3700-06 N. Fremont St. / 908-10 W. Waveland Ave

6558 N Richmond St

Columbia Gardens

4412-4426 N Saint Louis Ave

3709-3711 N Wilton Ave

3727 N. Fremont

732 W. Grace / 3803-3809 N. Broadway

Crowder Place

714 N Grace St

716 N Grace St

6705-6737 N California Ave

665 W Sheridan Rd

3700-3706 N Fremont St

The Maynard at 700 W Grace

Halsted Flats

4137-4143 N Kimball Ave

3709 N. Fremont

848 - 850 Waveland Ave.

801-811 W Bradley Pl

815-823 W Bradley Pl

3740-3750 N. Pine Grove

816 W Waveland

Residences at Addison Clark

920-22 W Addison

The Broadview

3720-3728 N Pine Grove Ave

900 W Addison St

3727 N Pine Grove

Waveland Park Court

The Addison - 915 W Addison St
Chicago, IL Local Guide

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Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,369 Studio Apartments in Chicago with rent ranges from $550 to $6,511 with an average price of $1,928.
What is the current price range for One Bedroom Chicago Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Chicago ranges from $650 to $15,069 with an average monthly rent of $2,427.
What does renting a Two Bedroom Apartment in Chicago cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chicago range from $650 to $18,797. Today's average rental price for Two Bedrooms here is $2,974.
How expensive are Chicago Three Bedroom Apartments?
There are currently 5,029 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $883 to $38,481 - averaging $3,704 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

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.

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.

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.

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

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.

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.

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.

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.