
Apartments near Winchester Plaza in Chicago, IL (3,785 Rentals)


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

900 W Addison St

3727 N Pine Grove

3720-3728 N Pine Grove Ave

Waveland Park Court

The Addison - 915 W Addison St

Town Hall Apartments

847 W Addison St

Angelus Apartments

3509-3511 W Belle Plaine Ave

612 W Patterson

3705 N Kedzie Ave.

3544 North Halsted Apartments

Pine Grove Apartments

3616 N. Pine Grove Ave.

Reside on Pine Grove

The Flower Flat

3613 N Pine Grove Ave

536 W. Addison

3842-44 N Bernard St

510-34 W. Addison St.

3731-3715 N Kimball Ave

3502-3508 W Grace St

3517-3521 W Grace St

3356 W Columbia Ave

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Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,256 Studio Apartments in Chicago with rent ranges from $595 to $5,184 with an average price of $2,027.
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 $640 to $9,987 with an average monthly rent of $2,466.
What does renting a Two Bedroom Apartment in Chicago cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chicago range from $500 to $18,797. Today's average rental price for Two Bedrooms here is $3,039.
How expensive are Chicago Three Bedroom Apartments?
There are currently 5,003 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $883 to $38,481 - averaging $3,665 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

Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
Written by: Nicole Harms
I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.

Chicago Relocation 101: Mastering Utilities, Registration, and the CTA
Written by: Nicole Harms
Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.

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.

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.
Articles, How-To's, and Tips

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.

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.

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.

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.