2025 Compare Cities Overview:
Windermere, FL vs Chicago, IL

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Highlights
Are people in Chicago older or younger than people in Windermere?
- The Median Age in Chicago is 17.8 years younger than in Windermere.

Are housing costs cheaper in Chicago or Windermere?
- Chicago housing costs are 58.8% less expensive than Windermere housing costs.

Which city has a longer commute, Chicago or Windermere?
- The average commute for residents of Chicago is 8.0 minutes longer than it is for residents of Windermere.

Things to do in Windermere?
Living in Windermere, FL is an experience like no other. With its idyllic atmosphere and close proximity to numerous attractions, you will never be bored here. It's the perfect combination of suburban life with a taste of Southern hospitality. The weather is typically sunny and warm, with temperatures remaining moderate year-round. Plus, you can enjoy stunning views of Lake Down and the surrounding green spaces while strolling around town. There's something for everyone in Windermere; you can shop at nearby malls or spend time outdoors kayaking or fishing on the lake. Whether you're looking for a quiet place to call home or an exciting adventure, Windermere has it all!

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.

 Windermere, FLChicago, ILUnited States
 Population  Unlock2,742,119329,725,481
 Median Income$131,392  Unlock$69,021
 Median Age  Unlock35.138.4
 Avg. Home Price$689,100  Unlock$338,100
 Unemployment Rate  Unlock9.0%6.0%
 Avg. Commute Time26.65  Unlock26.38
Reviews for Windermere    3 Reviews

I moved to Windermere from Chicago and I am having a difficult time adjusting here. Sure, the weather is great, but everything else is not. I have to drive for long  More

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Windermere, Florida is home to many top athletes and famous people including Tiger Woods & Shaq O'Neil. This is a quaint little town that guards itself against too much  More

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Over 16 years ago

I've spent the last 5 years in Windermere Fl. and 31 years in the state of Florida. Windermere is a small town set amongst the Butler Chain of Lakes. It has it's older  More

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Reviews for Chicago    270 Reviews

I've lived in Chicago city and later moved to suburbs when family size increased. Absolutely love this city. This is the cleanest and most beautiful among the major  More

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Chicago is probably the best value in a major city that you can find and my personal favorite city. It will become increasingly important as climate change makes the  More

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I've live on north side and south side, UIC medical center. Don't move here go to the north side. No good amenities, if you get bored with one there is no other choices.  More

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