
Apartments near Winchester Plaza in Chicago, IL (3,828 Rentals)


4941-4945 N Saint Louis Ave

754-756 W Bittersweet Pl

3616 N Marshfield Ave

5656 N Kimball Ave

1928 W Addison St

4038 N Clarendon Ave

6701 N Bosworth Ave

3639 N Greenview Ave

2014 W Addison St

6317-6323 N Sacramento Ave

3353-3355 W Wilson Ave

Cullom Park, LLC

4030 N Clarendon Ave

750 W Bittersweet Pl

1325-1333 W North Shore Ave

1300-1306 W Albion Ave

6532 N Washtenaw Ave

4701 N Bernard St

915 W Dakin St

3708-10 N Lakewood Ave

3626 N. Oakley 3 unit on 30ft lot

5700 N Kimball Ave

2912-2914 W Devon Ave

1627-1637 W Columbia Ave

900 W Dakin St

4901 N Saint Louis Ave

3709 N Lakewood Ave

6254 N Whipple St

744-746 W Bittersweet Place

930 W Sheridan Rd

746 W Bittersweet Pl

4022 N Clarendon Ave

4020 N Clarendon Ave

Condominiums

6656 N Glenwood Ave

1644 W Addison St

3615 N Ashland Ave

3554 N Hermitage Ave

2154 W Addison St

6700 N Newgard Ave

742 W Bittersweet Pl

1630 W Columbia Ave

751-757 W Bittersweet Pl

3300 W Pensacola Ave

6226 N Albany Ave

4256 N Sawyer Ave

3605 Bell

3717 N Magnolia Ave

3706 N Magnolia St

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Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,423 Studio Apartments in Chicago with rent ranges from $550 to $5,931 with an average price of $1,925.
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 $525 to $11,280 with an average monthly rent of $2,480.
What does renting a Two Bedroom Apartment in Chicago cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chicago range from $762 to $21,495. Today's average rental price for Two Bedrooms here is $3,062.
How expensive are Chicago Three Bedroom Apartments?
There are currently 4,983 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $883 to $38,481 - averaging $3,857 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

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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.