
Apartments near Winchester Plaza in Chicago, IL (3,877 Rentals)


4036 N Ashland Ave, Unit 36-2E

824 W Waveland Ave, Unit 827-S1

2175 W Giddings St, Unit 1

5945 N Paulina St, Unit 5951-1W

1545 W Glenlake Ave, Unit 2D

4244 N Spaulding Ave, Unit 3

4638 N Hamilton Ave, Unit 1F

2205 W Eastwood Ave, Unit 2e

1456 W Irving Park Rd, Unit 2

3935 N Janssen Ave, Unit 3941-1E

3921 N Pine Grove Ave, Unit 3914-3W

618 W Patterson Ave, Unit 605

4838 N Wolcott Ave, Unit GDN

6454 N Newgard Ave, Unit 2

941 W Grace St, Unit 202

3730 N Sheffield Ave, Unit 3708-407

3801 N Pine Grove Ave, Unit 304

3755 N Pine Grove Ave, Unit 3

1553 W Hollywood Ave, Unit 1

1123 W Patterson Ave, Unit 3

2175 W Giddings St, Unit 1

2022 W Montrose Ave, Unit 1A

4452 N Sheridan Rd, Unit 2

4027 N Kenmore Ave, Unit 101

3049 W Berteau Ave, Unit #3

5310 N Ashland Ave, Unit 3

2175 W Giddings St, Unit 1F

4409 N Wolcott Ave, Unit STU

5851 N Virginia Ave, Unit Unit 2

3817 N Fremont St, Unit #3829.5-W3

656 W Sheridan Rd, Unit 661-801

820 W Waveland Ave, Unit #816-14

2177 W Giddings St, Unit 2175-1

5647 N Ashland Ave, Unit 2

1555 W Hollywood Ave, Unit Stu

4913 N Hermitage Ave, Unit 2
Chicago, IL Local Guide

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Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,360 Studio Apartments in Chicago with rent ranges from $575 to $7,500 with an average price of $1,919.
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 $450 to $9,450 with an average monthly rent of $2,383.
What does renting a Two Bedroom Apartment in Chicago cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chicago range from $750 to $18,797. Today's average rental price for Two Bedrooms here is $2,917.
How expensive are Chicago Three Bedroom Apartments?
There are currently 4,959 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $788 to $38,481 - averaging $3,603 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

How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!












