2025 Compare Cities Overview:
Winchester, MA vs Oak Brook, IL

Are people in Oak Brook older or younger than people in Winchester?
- The Median Age in Oak Brook is 11.5 years older than in Winchester.

Are housing costs cheaper in Oak Brook or Winchester?
- Oak Brook housing costs are 36.3% less expensive than Winchester housing costs.

Which city has a longer commute, Oak Brook or Winchester?
- The average commute for residents of Oak Brook is 3.2 minutes shorter than it is for residents of Winchester.

Things to do in Winchester?
Winchester is a lovely suburban town located just 8 miles north of Boston in Middlesex County Massachusetts. Serving as home to some of New England’s oldest homes Winchester Center is a great place to explore history while also benefiting from access to Boston’s cultural assets. This well ranked school district also offers families plenty of educational opportunities as well.

Things to do in Oak Brook?
Living in Oak Brook, IL is like living in a modern, contemporary paradise. It has everything one could want: great schools, top-notch restaurants, world-class shopping centers, and plenty of outdoor activities. The community is very close-knit and friendly, making it easy to make new friends and stay connected with old ones. There are plenty of parks to explore and nature trails to enjoy. The area also provides an array of cultural events throughout the year, like concerts and art festivals that bring together people from all walks of life. Plus, the city is only a short drive away from Chicago, so you can always take advantage of all the metropolitan attractions there as well. All in all, Oak Brook is an ideal place to call home!