Find Rentals in Chicago

Houses for Rent

Apartments for Rent

See Newest Listings

Explore Listings

Browse Apartments

Property Managers

List Your Rentals

Listings Quality Policy

Renter Resources

Avoid Scams & Fraud

Rent vs. Buy Calculator

Rent Affordability Calculator

Help & Support

1 / 10

New - 2 days ago

Verified

Pet Friendly

- Save listing search
- Report this listing

4500 N Winchester Ave

Chicago, IL 60640 - Cook County

Apartment

2 beds

1 baths

1,100 sqft

About 4500 N Winchester Ave

Welcome to 4500win, presented by Hayes Properties. We have several units available for lease. For more information and to schedule a showing, please contact us. Heat, Water, Sewer, Trash, Ss range, Ss dishwasher, Ss refrigerator & Ss microwave. Cats Allowed.

RentalSource last checked: June 12, 2026 · 1:54 PM ET

Last updated: June 10, 2026 at 4:55 PM ET

Managed by: Hayes Properties · (773) 929-7050

Listing data quality - We review listings daily to detect outdated, duplicate, or misleading information.

Property Summary

Property Type:	Apartment
Rental Fee:	$1,995
Bedrooms:	2 beds
Bathrooms:	1 baths

Size:	1,100 sqft
Pet Friendly:	Yes
Listing Status:	Active
ID:	83790179

Property Amenities

• Dishwasher

• Microwave

• Pet Friendly

• Refrigerator

Additional Details

Apartment for rent in Chicago for $1,995 with 2 beds, 1 bath, 1,100 sqft, pet friendly and located at 4500 N Winchester Ave in Chicago, IL 60640. The rental price of $1,995 is 32.6% ($963) lower than the average rent of $2,958 for a 2 bedroom apartment in Chicago, IL and 30.0% ($853) lower than the average rent of $2,848 for a 2 bedroom apartment in Cook County. 4500 N Winchester Ave was advertised by Hayes Properties on June 10, 2026 at 7:57 AM ET and last checked today at 1:54 PM ET.

Affordability Calculator

Can I afford to live at 4500 N Winchester Ave?

Bedrooms

2 bedrooms

Rent-to-income ratio

30%

10% Recommended 50%

Move the slider to select the percentage of your monthly income you're comfortable spending on rent. Typically, it's advised to spend about 30% or less on housing.

Recommended income

$79,800 /year

With your chosen rent-to-income ratio, an annual income of $79,800 is recommended to comfortably afford this 2-bedroom rental priced at $1,995 per month.

For more information on rent affordability, visit our rent calculator or rent vs. buy calculator.

Apartment for rent

$1,995

Rent Affordability Calculator

Interested in 4500 N Winchester Ave?

Find out more about this property & see if it's available now.

Property managed by:

Hayes Properties
(773) 929-7050

Avoid rental scams - Situations involving wire transfers or a landlord who can't meet you in person can be red flags.

Ask About 4500 N Winchester Ave

4500 N Winchester Ave, Chicago, IL 60640 - Apartment for Rent

What's New on the Blog

Explore recent posts on our blog, curated for renters, landlords, and industry pros.

Single family rental property evaluated for loan financing

Landlord Resources

How to Get a Loan for a Rental Property

Rental property loans differ from traditional mortgages, needing larger down payments, higher interest rates, and reserves, often disregarding projected rental income.

June 10, 2026•11 min read

Empty rental unit with natural light, ready for showings and tenant screening

Landlord Resources

10 Steps to Find Renters and Fill Your Vacancy

Vacancies drain cash quickly, and rushed approvals drain it even faster. A repeatable tenant-finding system attracts qualified applicants, filters early, and maintains consistent standards. This consistency also lowers Fair Housing risks under pressure.

June 3, 2026•11 min read

Huntsville, AL

Best Cities for First-Time Renters

Some cities make first-time renting harder than it needs to be with limited inventory and strict screening, which can magnify minor issues. These cities offer more flexibility, better availability, and easier recovery for new renters.

May 27, 2026•11 min read

Property management contract and financial documents on a desk

Landlord Resources

What a Property Manager Actually Does

Hiring a property manager shifts stress, but it trades direct control for operational coverage. The contract outlines responsibilities, so clarity before signing is key to avoiding costly regrets.

May 20, 2026•10 min read

Paying rent online with a credit card using a laptop

Renter Resources

Using a Credit Card to Pay Rent

Paying rent with a credit card is only beneficial if the fees are low and you pay the balance in full each month. High processing fees, cash-advance charges, and increased utilization can outweigh rewards and delay rent posting.

May 13, 2026•11 min read

Reviewing lease paperwork before adding someone to an existing lease

Renter Resources

Best Way to Add Someone to an Existing Lease

Adding an adult occupant mid-lease can lead to lease violations, unexpected fees, or shared debt. To avoid issues, get landlord approval, handle screening, and complete the necessary paperwork to clarify everyone's rights and responsibilities.

May 6, 2026•11 min read

Dallas, TX

10 Cities People Are Moving to in 2026

Migration is reshaping rental demand. These cities show ongoing inbound moves driven by job growth, housing trade-offs, and lifestyle fit. Use these signals to time a move, price a rental, or identify tightening competition.

April 29, 2026•11 min read

Lease agreement with house keys illustrating security deposit alternatives

Landlord Resources

Security Deposit Alternatives for Renters and Landlords

Lower upfront costs can make signing easier, but fees, claim rules, and reimbursement risks often surface later. Compare the most common options so you can choose what actually fits your lease and tolerance for risk.

April 22, 2026•11 min read

Envelope labeled non-renewal of lease on a desk with rental paperwork

Landlord Resources

How to Write a Non-Renewal Lease Letter to Tenants

A non-renewal letter ends a lease cleanly when it’s clear, timely, and documented. Use the proper notice period, neutral language, and outline move-out steps to avoid disputes and compliance issues.

April 15, 2026•12 min read

List Your Property for Rent

Are You a Rental Professional?

Advertise on RentalSource, Zillow, Realtor.com, Zumper and more to attract quality tenants faster and take your listings to the next level.

Was this page helpful?