348 Park Ave
GlencoeIL60022
Cheap Homes for Rent in Winnetka, IL from $1,600 (9 Rentals)
Search the lowest-cost Homes available for rent right now in Winnetka.
899 Green Bay Rd
WinnetkaIL60093
373 Hazel Ave
GlencoeIL60022
901 Green Bay Rd
WinnetkaIL60093
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
896 Green Bay Rd
WinnetkaIL60093
894 Green Bay Rd
WinnetkaIL60093
901 Green Bay Rd
WinnetkaIL60093
822 Elm St
WinnetkaIL60093
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
545 Chestnut St
WinnetkaIL60093
Showing Results 1-9, Page 1 of 1
Winnetka, IL Local Guide
Lakeshore Panorama by Wesley Fryer is licensed under CC BY 2.0
How much does it cost to rent a home in Winnetka?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winnetka 2 Bedroom Homes for Rent | $2,201 | $1,995 | $2,690 |
| Winnetka 3 Bedroom Homes for Rent | $3,607 | $2,250 | $6,500 |
| Winnetka 4 Bedroom Homes for Rent | $9,077 | $6,233 | $10,000+ |
| Winnetka 5 Bedroom Homes for Rent | $12,610 | $4,350 | $10,000+ |
| Winnetka 6 Bedroom Homes for Rent | $15,000 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Winnetka
Explore Winnetka
Winnetka, IL Local Guide
- Nearby Cities
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Cheapest Available Winnetka Apartments for Rent
The cheapest available apartment rental in Winnetka, IL is a 1 Bed unit found at Old Orchard Residences in the Gross Point neighborhood priced from $1,685. 458 Winnetka Ave in the Gross Point neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,845. Here is today’s list of the most affordable Winnetka apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Old Orchard Residences | A1 | 1BR,1BA | $1,685 |
| 458 Winnetka Ave | 1 BED 1 Bath | 1BR,1BA | $1,845 |
| Elaine Luxury Apartments | A0 | 1BR,1BA | $1,900 |
Best Value Apartments for Rent in Winnetka, IL
As of January 26, 2026 the best value apartment in the Winnetka area is the $1.33 price per square foot 244 Eaton St Model at 244 Eaton St, Unit 1 in the in the Gross Point neighborhood starting from $2,000. The second greatest value Winnetka apartment is the 338 Tudor Ct Model at 338 Tudor Ct, Unit 347-02 starting at $2,995 with a $2.72 price per square foot in the Braeside neighborhood. Here is today’s list of the best values for Winnetka apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 244 Eaton St, Unit 1 | 244 Eaton St | 1BR,1BA | $1.33 |
| 338 Tudor Ct, Unit 347-02 | 338 Tudor Ct | 3BR,1BA | $2.72 |
| 545 Chestnut St, Unit 817-206 | 545 Chestnut St | 1BR,1BA | $2.44 |
| 913 Green Bay Rd, Unit J07P | 913 Green Bay Rd | 2BR,1BA | $2.44 |
| 890 Green Bay Rd, Unit J07W | 890 Green Bay Rd | 2BR,1BA | $2.44 |
| Old Orchard Residences | A1 | 1BR,1BA | $2.25 |
| 458 Winnetka Ave | 1 BED 1 Bath | 1BR,1BA | $2.46 |
| 435 Park Ave, Unit J08P | 435 Park Ave | 1BR,1BA | $2.42 |
| 894 Green Bay Rd, Unit 894A-01 | 894 Green Bay Rd | 1BR,1BA | $2.64 |
| 342 Park Ave, Unit A06C | 342 Park Ave | 1BR,1BA | $2.56 |
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.
Read Article
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
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleA 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
Read ArticleQuick Rent Budget Calculator
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Best Local Schools in Winnetka, IL
Hubbard Woods Elementary School
Winnetka School District 36
Public School - Grades K-4 (324)
10 out of 10
New Trier Township H S Winnetka
New Trier Twp Hsd 203 School District
Public School - Grades 1-12 (2856)
10 out of 10
School data provided by Great Schools
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winnetka, IL Rentals by Map
See the most popular apartments and homes in Winnetka, IL
Frequently Asked Questions about Winnetka
What type of rentals are currently available in Winnetka?
There are currently 95 Apartments for Rent in Winnetka, IL with pricing that ranges from $1,395 to $15,925. There are also 46 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winnetka ranging from $1,695 to $29,000.
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 $1,695 to $29,000 with an average monthly rent of $7,418.
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
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.
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.