2025 Compare Cities Overview:
Winnetka, IL vs Cheshire, CT

Change Cities
Highlights
Are people in Cheshire older or younger than people in Winnetka?
- The Median Age in Cheshire is 2.8 years older than in Winnetka.

Are housing costs cheaper in Cheshire or Winnetka?
- Cheshire housing costs are 69.7% less expensive than Winnetka housing costs.

Which city has a longer commute, Cheshire or Winnetka?
- The average commute for residents of Cheshire is 11.0 minutes shorter than it is for residents of Winnetka.

Things to do in Winnetka?
Winnetka, Illinois is a vibrant village located in the northern suburbs of Chicago. The area offers plenty of activities for all kinds of interests, from shopping and dining to sports and recreation. Winnetka residents also have access to excellent educational opportunities, with pre-Kindergarten through college prep courses available at top schools. Nature lovers can explore the Lake Michigan shoreline or numerous parks and forest preserves nearby. Winnetka is perfect for those looking for an urban lifestyle that still retains its small-town charm!

Things to do in Cheshire?
Cheshire, CT is a town located in New Haven County in southern Connecticut. It was founded in 1780 and is known for its quiet suburbs and green spaces. There are several parks within Cheshire that offer outdoor activities like hiking and camping, as well as charming historic buildings such as Lock 12 Historic Park and Witch Meadow Lake Beach Park.

 Winnetka, ILCheshire, CTUnited States
 Population  Unlock28,766329,725,481
 Median Income$250,001  Unlock$69,021
 Median Age  Unlock45.438.4
 Avg. Home Price$1,348,300  Unlock$338,100
 Unemployment Rate  Unlock5.2%6.0%
 Avg. Commute Time37  Unlock26.38
Reviews for Winnetka    2 Reviews

Having had children attend both public and private schools. I would say the private schools are better. While the public schools are fine, there isn't any way to measure  More

   |    Reply

This idyllic, leafy, close-in suburb north of Chicago comes straight out of a Frank Capra (or John Hughes - see Home Alone for a view of the housing stock and  More

   |    Reply

Start Your Review of Winnetka

Reviews for Cheshire    2 Reviews

Over 12 years ago

Overall excellent town for raising kids. When comparing towns look at the numbers, they take out any biases. You get the most for your family in  More

   |    Reply

Over 15 years ago

I love Cheshire because the people there are friendly,mind their own business and the town is so pretty! I live in Meriden and I go to Cheshire often just to relax.  More

   |    Reply

Start Your Review of Cheshire


Premium Subscription
Includes Cost of Living compares for child care, utilities, transportation, health, taxes, housing for home owners vs renters, weather, insurance premiums and so much more.


The premier source for comprehensive city data for over 30 years.

© Best Places. All rights reserved.