
Apartments near Winchester Plaza in Chicago, IL (3,791 Rentals)


5926-5934 1/2 N Paulina St

5909 N Paulina St

4701-4703 N Malden St

4435 N Paulina St

Gunnison Street Lofts

1900-1906 W Montrose Ave

1918-1930 W Montrose Ave

5439 N Broadway

1513 W Sunnyside Ave

1217 W Lawrence Ave

5724 N Ridge Ave

5684 N Ridge Ave

1501-1503 W Ardmore Ave

5732 N Ridge Ave

5806 N Ridge Ave

4749-4755 N Magnolia Ave

2500-2502 W Eastwood Ave

5022-5030 N Winthrop Ave

4649-4653 N Malden St

5874-5884 N Ridge Ave

4866-4870 N Talman Ave

2100-2110 W Montrose Ave

5206-5212 N Winthrop Ave

Delmar Apartments

5618 N Maplewood Ave

2601 W Lawrence Ave

5747 N Ridge Ave

1901 W Montrose Ave

5032 N Winthrop Ave

4401-4411 N Hamilton Ave

4441 N Ashland Ave

4935 N Washtenaw Ave

5823 N Ridge Ave

5316-5318 N Winthrop Ave

5700-04 N Campbell Ave

2540 W Leland Ave

1108 W Winona St

5803-5807 N Ridge Ave

5544-5546 N Broadway St

5739-5745 N Ridge Ave

4420-4422 N Ashland Ave

4400-4410 N Hamilton Ave

2700 W Argyle St

2618-2636 W Catalpa Ave

5809 N Ridge Ave

2654-2658 W Ainslie St

5941-5951 N Paulina St

2501-2503 W Eastwood Ave

5710-5712 N Wayne Ave

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Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,206 Studio Apartments in Chicago with rent ranges from $595 to $9,919 with an average price of $2,040.
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 $10,307 with an average monthly rent of $2,473.
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 $3,043.
How expensive are Chicago Three Bedroom Apartments?
There are currently 4,968 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $883 to $38,481 - averaging $3,748 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

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.