
Apartments near Winchester Plaza in Chicago, IL (3,913 Rentals)


6253-6257 N Greenview Ave

2145-2155 W Highland Ave

Thorndale Beach North Condominium

2131-2141 W Highland Ave

6214-6216 N Wayne Ave

Mozart 4401-07 N.

1526-1528 W Rosemont Ave

2225 W Highland Ave

1451-1453 W Rosemont Ave

1247-1249 W Granville Ave

1540-1542 W Rosemont Ave

4011 N Paulina St

1624-1626 W Highland Ave

3001 W Leland Ave

936-940 W Agatite

1536-1538 W Rosemont Ave

2201-2207 W Highland Ave

1241-1243 W Granville Ave

4339-4345 N Kenmore Ave

1532-1534 Rosemont Ave

2335 W Belle Plaine Ave

6044 N Washtenaw Ave

4054 N Western Ave

1839-1843 W Irving Park Rd

1306-1308 W Granville Ave

6356-6358 N Paulina St

6222-6224 N Wayne Ave

6230 N Wayne Ave

4007 N Paulina St

1441-1443 W Rosemont Ave

6101 N Washtenaw

Buena Pointe

1522-1524 W Rosemont Ave

4312 N Kenmore Ave

1435-1437 W Rosemont Ave

3105 W Argyle St

945 W Agatite Ave

1516-1518 W Rosemont Ave

4335 N Kenmore Ave

4331 N Kenmore Ave

1447-1449 W Rosemont Ave

3100 W Argyle St

6308 N Oakley Ave

930-934 W Agatite Ave

935 W Agatite Ave

1427-1429 W Rosemont Ave

1431-1433 W Rosemont Ave

3115-3123 W Foster Ave

913-919 W Sunnyside
Chicago, IL Local Guide

Browse Top Apartments in Chicago
Explore Chicago
Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,402 Studio Apartments in Chicago with rent ranges from $550 to $5,728 with an average price of $1,914.
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 $15,732 with an average monthly rent of $2,422.
What does renting a Two Bedroom Apartment in Chicago cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chicago range from $700 to $21,623. Today's average rental price for Two Bedrooms here is $2,988.
How expensive are Chicago Three Bedroom Apartments?
There are currently 4,994 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $755 to $38,481 - averaging $3,724 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.