2026 Compare Cities Overview:
Chesapeake, VA vs Winter Park, FL

Are people in Winter Park older or younger than people in Chesapeake?
- The Median Age in Winter Park is 8.2 years older than in Chesapeake.

Are housing costs cheaper in Winter Park or Chesapeake?
- Winter Park housing costs are 37.8% more expensive than Chesapeake housing costs.

Which city has a longer commute, Winter Park or Chesapeake?
- The average commute for residents of Winter Park is 1.8 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 Winter Park?
Winter Park, FL is nestled between Orlando & Sanford offering magnificent mansions combined with vibrant street scenes fulls fabulous restaurants and boutique stores. Visitors here can enjoy swan boats cruising across Lake Virginia or find tranquility at Leu Gardens which offers breathtaking views no matter which season you visit during!