2025 Compare Cities Overview:
Chesapeake, VA vs Winston, OR

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Highlights
Are people in Winston older or younger than people in Chesapeake?
- The Median Age in Winston is 1.8 years younger than in Chesapeake.

Are housing costs cheaper in Winston or Chesapeake?
- Winston housing costs are 18.2% less expensive than Chesapeake housing costs.

Which city has a longer commute, Winston or Chesapeake?
- The average commute for residents of Winston is 6.4 minutes shorter than it is for residents of Chesapeake.

Things to do in Chesapeake?
Chesapeake, Virginia is a vibrant city known for its beautiful scenery and bustling downtown. Enjoy the temperate climate while exploring its attractions such as outdoor trails, lakeside beaches, shopping centers, delicious restaurants and various entertainment venues. With its excellent shopping centers, lively nightlife and cultural events happening throughout the year, Chesapeake is sure to provide something to keep everyone entertained!

Things to do in Winston?
Living in Winston, OR is a unique and delightful experience. Located in the heart of Douglas County, it’s a town filled with natural beauty, friendly neighbors, and plenty of opportunities to explore the outdoors. There are plenty of places to shop, dine, and enjoy the fresh air. The town has some excellent hiking trails, as well as several parks that provide a great spot for picnics or simply taking in some fresh air. There's also several nearby lakes where you can go fishing or just relax under the stars and enjoy the peacefulness of nature. Winstons small-town charm makes it easy to make friends quickly and settle into your new home away from home.

 Chesapeake, VAWinston, ORUnited States
 Population  Unlock5,591329,725,481
 Median Income$85,563  Unlock$69,021
 Median Age  Unlock35.338.4
 Avg. Home Price$359,000  Unlock$338,100
 Unemployment Rate  Unlock7.3%6.0%
 Avg. Commute Time25.87  Unlock26.38
Reviews for Chesapeake    33 Reviews

I lived here in Virginia near the Cedar Rd. not so far from Tidewater Community college. If you want a great place to live to raise children, its Chesapeake  More

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I live around this area currently, in the "Hampton Roads". Which consists of Virginia Beach, Suffolk, Norfolk, Portsmouth, Newport News, Hampton, and Chesapeake. We're  More

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I was born in Hampton Roads and lived there for more than 65 years. We lived in the city of Chesapeake for three years from 2014-2017. Frankly, we were very glad to  More

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