2025 Compare Cities Overview:
Chicago, IL vs Winter Park, FL

Are people in Winter Park older or younger than people in Chicago?
- The Median Age in Winter Park is 10.2 years older than in Chicago.

Are housing costs cheaper in Winter Park or Chicago?
- Winter Park housing costs are 74.2% more expensive than Chicago housing costs.

Which city has a longer commute, Winter Park or Chicago?
- The average commute for residents of Winter Park is 10.6 minutes shorter than it is for residents of Chicago.

Things to do in Chicago?
Chicago, Illinois is an American icon. Located along the beautiful shores of Lake Michigan, it's a vibrant city with an energy like no other. It's renowned for its world-class museums and galleries, rich history and stunning architecture. With hundreds of parks and beaches to explore, amazing restaurants to sample, and a bustling nightlife scene - Chicago has something for everyone! It's the home of diverse cultures and international events, making it one of the most unique cities in the US.

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!