366 Park Ave, Unit 20
366 Park Ave
GlencoeIL60022
Cheap Homes for Rent in Winnetka, IL from $1,500 (24 Rentals)
Search the lowest-cost Homes available for rent right now in Winnetka.
918 Green Bay Rd, Unit 2F
918 Green Bay Rd
WinnetkaIL60093
918 Green Bay Rd, Unit #3C
918 Green Bay Rd
WinnetkaIL60093
918 Green Bay, Unit C4
918 Green Bay
NorthfieldIL60093
915 Green Bay Rd, Unit 3C
915 Green Bay Rd
WinnetkaIL60093
10115 Old Orchard Ct
SkokieIL60076
918 Green Bay Rd, Unit B4
918 Green Bay Rd
WinnetkaIL60093
731 Elm St, Unit 733-301
731 Elm St
WinnetkaIL60093
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
733 Elm, Unit 103
733 Elm
NorthfieldIL60093
730 Elm St, Unit 301
730 Elm St
WinnetkaIL60093
733 Elm St, Unit 301
733 Elm St
WinnetkaIL60093
343 Park Ave, Unit 7
343 Park Ave
GlencoeIL60022
366 Park Ave, Unit 70
366 Park Ave
GlencoeIL60022
366 Park Ave, Unit 30
366 Park Ave
GlencoeIL60022
343 Park Ave, Unit 3
343 Park Ave
GlencoeIL60022
918 Green Bay Rd, Unit 3E
918 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.
916 Green Bay Rd, Unit 918-2L
916 Green Bay Rd
WinnetkaIL60093
918 Green Bay Rd, Unit E4
918 Green Bay Rd
WinnetkaIL60093
918 Green Bay Rd, Unit 3A
918 Green Bay Rd
WinnetkaIL60093
918 Green Bay Rd, Unit 2L
918 Green Bay Rd
WinnetkaIL60093
918 Green Bay, Unit L2
918 Green Bay
NorthfieldIL60093
733 Elm, Unit 203
733 Elm
NorthfieldIL60093
733 Elm St, Unit 302
733 Elm St
WinnetkaIL60093
731 Elm St, Unit 302
731 Elm St
WinnetkaIL60093
Cash 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.
Showing Results 1-24, Page 1 of 1
Winnetka, IL Local Guide
How much does it cost to rent a home in Winnetka?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winnetka 2 Bedroom Homes for Rent | $3,216 | $2,400 | $3,850 |
| Winnetka 3 Bedroom Homes for Rent | $3,958 | $2,250 | $6,200 |
| Winnetka 4 Bedroom Homes for Rent | $7,116 | $3,950 | $8,900 |
| Winnetka 5 Bedroom Homes for Rent | $15,150 | $7,500 | $10,000+ |
| Winnetka 6 Bedroom Homes for Rent | $35,000 | $10,000 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 460 Winnetka Ave. | Winnetka - 1 bedroom 770 | 1BR,1BA | $1,870 |
| The Residences of Wilmette | C1 | Studio,1BA | $2,895 |
Best Value Apartments for Rent in Winnetka, IL
As of June 14, 2026 the best value apartment in the Winnetka area is the $0.80 price per square foot 511 Park Dr Model at 511 Park Dr, Unit 511 Park Dr, Kenilworth in the in the Gross Point neighborhood starting from $1,975. The second greatest value Winnetka apartment is the 3BR/2.5BA Model at Trevian Townhomes starting at $4,037 with a $2.45 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 511 Park Dr, Unit 511 Park Dr, Kenilworth | 511 Park Dr | 3BR,1BA | $0.80 |
| Trevian Townhomes | 3BR/2.5BA | 3BR,2.5BA | $2.45 |
| Elaine Luxury Apartments | A6 | 2BR,1BA | $3.06 |
| 460 Winnetka Ave. | Winnetka - 1 bedroom 770 | 1BR,1BA | $2.43 |
| 220 Park Ave, Unit J03P | 220 Park Ave | 1BR,1BA | $2.42 |
| 545 Chestnut St, Unit E545-301 | 545 Chestnut St | 1BR,1BA | $3.21 |
| 547 Chestnut St | 547 Chestnut St | 1BR,1BA | $2.85 |
| 307 Ridge Rd, Unit First Floor | 307 Ridge Rd | 1BR,1BA | $2.50 |
| 924 Green Bay Rd | 924 Green Bay Rd | Studio ,1BA | $3.09 |
| 338 Tudor Ct | 338 Tudor Ct | Studio ,1BA | $3.91 |
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 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 ArticleReal 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.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Best Local Schools in Winnetka, IL
Crow Island Elementary School
Winnetka School District 36
Public School - Grades K-5 (346)
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 92 Apartments for Rent in Winnetka, IL with pricing that ranges from $1,500 to $17,556. There are also 53 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winnetka ranging from $1,565 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 $1,565 to $35,000 with an average monthly rent of $9,699.
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 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.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.