369 Hazel Ave, Unit B9
369 Hazel Ave
GlencoeIL60022
Cheap Homes for Rent in Winnetka, IL from $1,595 (15 Rentals)
Search the lowest-cost Homes available for rent right now in Winnetka.
369 Hazel Ave, Unit D8
369 Hazel Ave
GlencoeIL60022
366 Park Ave, Unit 70
366 Park Ave
GlencoeIL60022
369 Hazel Ave, Unit D3
369 Hazel Ave
GlencoeIL60022
369 Hazel Ave, Unit B10
369 Hazel Ave
GlencoeIL60022
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.
916 Green Bay Rd
WinnetkaIL60093
918 Green Bay Rd, Unit 3E
918 Green Bay Rd
WinnetkaIL60093
1310 Wilmette Ave
WilmetteIL60091
894 Green Bay Rd, Unit 896A-09
894 Green Bay Rd
WinnetkaIL60093
946 Green Bay Rd, Unit 90A
946 Green Bay Rd
WinnetkaIL60093
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.
918 Green Bay Rd
WinnetkaIL60093
809 Elm St, Unit 3
809 Elm St
WinnetkaIL60093
809 Elm St, Unit 5
809 Elm St
WinnetkaIL60093
809 Elm St, Unit 2
809 Elm St
WinnetkaIL60093
909 Green Bay Rd
WinnetkaIL60093
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!
Showing Results 1-15, 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 | $2,758 | $1,950 | $4,300 |
| Winnetka 3 Bedroom Homes for Rent | $3,814 | $2,250 | $4,895 |
| Winnetka 4 Bedroom Homes for Rent | $5,807 | $3,700 | $9,900 |
| Winnetka 6 Bedroom Homes for Rent | $25,250 | $10,000 | $10,000+ |
| Winnetka 7 Bedroom Homes for Rent | $16,500 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Winnetka
Explore Winnetka
Winnetka, IL Local Guide
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Cheapest Available Winnetka Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Old Orchard Residences | A1 | 1BR,1BA | $1,700 |
| 460 Winnetka Ave. | Winnetka - 1 bedroom 770 | 1BR,1BA | $1,870 |
Best Value Apartments for Rent in Winnetka, IL
As of September 12, 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 2 Bed 2 Bath Model at HIGHPOINT Wilmette starting at $4,400 with a $3.12 price per square foot in the Central Street 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. |
|---|---|---|---|
| Trevian Townhomes | 3BR/2.5BA | 3BR,2.5BA | $2.35 |
| HIGHPOINT Wilmette | 2 Bed 2 Bath | 2BR,2BA | $3.12 |
| 924 Green Bay Rd, Unit 1 | 924 Green Bay Rd | 1BR,1BA | $1.75 |
| 460 Winnetka Ave. | Winnetka - 1 bedroom 770 | 1BR,1BA | $2.43 |
| Old Orchard Residences | A1 | 1BR,1BA | $2.27 |
| 910 Green Bay Rd, Unit 918-3E | 910 Green Bay Rd | 1BR,1BA | $2.13 |
| 894 Green Bay Rd | 894 Green Bay Rd | 1BR,1BA | $2.71 |
| 908 Green Bay Rd, Unit 3E | 908 Green Bay Rd | 1BR,1BA | $2.44 |
| 545 Chestnut St | 545 Chestnut St | 1BR,1BA | $3.07 |
| 307 Ridge Rd, Unit First Floor | 307 Ridge Rd | 1BR,1BA | $2.50 |
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.
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 ArticleNavigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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.
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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 86 Apartments for Rent in Winnetka, IL with pricing that ranges from $1,500 to $3,974. There are also 59 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winnetka ranging from $1,595 to $35,500.
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 $1,595 to $35,500 with an average monthly rent of $5,090.
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
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.
Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
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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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Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.