Cheap Homes for Rent in Winnetka, IL from $1,400 (19 Rentals)

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The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago

Chicago may cost more than the national average, but with the right neighborhood, a smart transit strategy, and a few local insider tips, living well in the Windy City is more achievable than you might think. Our local expert breaks down everything from rent and groceries to transportation and healthcare so you can plan your move with confidence.

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Looking for a rental near Chicago? These five cities offer excellent options! From small-town charm to excellent business options, you can't go wrong!

Winnetka, IL Local Guide

Cheapest Available Winnetka Apartments for Rent

 

The cheapest available apartment rental in Winnetka, IL is a 1 Bed unit found at 460 Winnetka Ave. in the Gross Point neighborhood priced from $1,870. Elaine Luxury Apartments in the Downtown Northbrook neighborhood has the second lowest priced unit, which is a 2 Beds apartment currently listed from $3,000. Here is today’s list of the most affordable Winnetka apartments for rent:

Apartment ListingModel NameBed/BathPriced From
460 Winnetka Ave.Winnetka - 1 bedroom 7701BR,1BA$1,870
Elaine Luxury ApartmentsA6-HC2BR,1BA$3,000
Trevian Townhomes3BR/2.5BA3BR,2BA$3,869

Best Value Apartments for Rent in Winnetka, IL

As of July 29, 2026 the best value apartment in the Winnetka area is the $2.35 price per square foot 3BR/2.5BA Model at Trevian Townhomes in the in the Gross Point neighborhood starting from $3,869. The second greatest value Winnetka apartment is the 244 Eaton St Model at 244 Eaton St, Unit 1 starting at $2,000 with a $1.33 price per square foot in the Gross Point neighborhood. Here is today’s list of the best values for Winnetka apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Trevian Townhomes3BR/2.5BA3BR,2.5BA$2.35
244 Eaton St, Unit 1244 Eaton St1BR,1BA$1.33
Elaine Luxury ApartmentsA62BR,1BA$3.06
460 Winnetka Ave.Winnetka - 1 bedroom 7701BR,1BA$2.43
220 Park Ave, Unit J03P220 Park Ave1BR,1BA$2.42
369 Hazel Ave, Unit C3369 Hazel AveStudio ,1BA$4.06
338 Tudor Ct338 Tudor CtStudio ,1BA$3.91
738 Lavergne Ave, Unit H738 Lavergne Ave3BR,2.5BA$38.50

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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Best Neighborhoods to Rent in Near Chicago's Top Employers: A Guide for Renters

A Local Expert's Guide to The 10 Best Chicago Neighborhoods near Major Local Employers. Find your perfect Chicago, IL apartment, condo, or rental home today at ApartmentHomeLiving.com

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A Local Expert's Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago

A Local Expert's guide to the Best Student Friendly Neighborhoods Near Colleges in the Chicago, IL metro area for affordable living. Find your perfect Chicago Student apartment, condo, or rental home today at ApartmentHomeliving.com

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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

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Frequently Asked Questions about Winnetka

What type of rentals are currently available in Winnetka?

There are currently 87 Apartments for Rent in Winnetka, IL with pricing that ranges from $1,495 to $3,850. There are also 58 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winnetka ranging from $1,425 to $35,000.

What is the current price range for Rental Homes in Winnetka?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winnetka ranges from $1,425 to $35,000 with an average monthly rent of $8,576.

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

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The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago

Written by: Nicole Harms

When choosing a place to live, there are many things you must consider. Your employer, your shopping preferences, and even schools are all important to think about. Yet cost of living is also important to know and plan for.

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Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible

Written by: Nicole Harms

I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.

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Chicago Relocation 101: Mastering Utilities, Registration, and the CTA

Written by: Nicole Harms

Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.

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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

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Rent According to Income: A Look at Income-Restricted Rentals

Written by: Robin Stewart

The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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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.

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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.

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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.