
Apartments near Winchester Plaza in Chicago, IL (3,897 Rentals)


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923 W Waveland Ave, Unit M07H

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1601 W Belle Plaine Ave, Unit 1

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923 W Waveland Ave

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4871 N Paulina St, Unit G

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4628 N Leavitt St, Unit GDN

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1907 W Larchmont Ave, Unit J01P

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3919 N Janssen Ave, Unit 3E

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3730 N Sheffield Ave, Unit 2

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4410 N Wolcott Ave, Unit A04W

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2519 W Leland Ave, Unit C1

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4742 N Sawyer Ave, Unit #2

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3614 N Bosworth Ave, Unit J09W

2205 W Eastwood Ave, Unit R03A

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4411 N Wolcott Ave, Unit R09A

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5668 N Ridge Ave, Unit ONE BEDROOM

1010 W Sunnyside Ave, Unit 1010-3

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4040 N Ashland Ave, Unit 3

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3607 N Damen Ave, Unit 1R

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3616 N Bosworth Ave, Unit 1R

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3614 N Bosworth Ave, Unit R01A

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3614 N Bosworth Ave, Unit M03H

4843 N Seeley Ave, Unit 4857-2

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2206 W Eastwood Ave, Unit A03N

2439 W Leland Ave, Unit 2520-C01

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4409 N Wolcott Ave

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4036 N Ashland Ave

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928 W Dakin St, Unit 305

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912 W Dakin St, Unit 917-305

3723 N Pine Grove Ave, Unit E3

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2251 W Lawrence Ave, Unit 103

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2207 W Eastwood Ave, Unit 2207-2N

2209 W Eastwood Ave, Unit 2N

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1913 W Larchmont Ave, Unit 3A

3723 N Pine Grove Ave, Unit J05W

5140 N Clark St, Unit 2

1913 W Larchmont Ave, Unit 3

1909 W Larchmont Ave, Unit 1911-2A

1909 W Larchmont Ave, Unit 1911-2A

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1909 W Larchmont Ave, Unit 2A

4414 N Whipple St, Unit 18-2

4414 N Whipple St, Unit 18-2

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3838 N Greenview Ave

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6231 N Kenmore Ave

915 W Waveland Ave, Unit 923-3B

3837 N Greenview Ave, Unit GDN

752 W Gordon Ter

3917 N Pine Grove Ave, Unit 3W

3723 N Pine Grove Ave, Unit W1

736 W Addison St, Unit A09W
Chicago, IL Local Guide

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Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,399 Studio Apartments in Chicago with rent ranges from $550 to $5,728 with an average price of $1,946.
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 $2,439.
What does renting a Two Bedroom Apartment in Chicago cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chicago range from $850 to $22,299. Today's average rental price for Two Bedrooms here is $2,980.
How expensive are Chicago Three Bedroom Apartments?
There are currently 4,992 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $883 to $38,481 - averaging $3,740 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.