Five Things We Gave up When We Moved from Chicago to Naples
Relocation August 9, 2026
Relocation August 9, 2026
Five things we gave up when we moved from Chicago to Naples, Florida. . . and what we gained instead.
🍂 Four real seasons → ☀️ 12 months of being outside
🚶♀️ Walking to everything → 🌊 Walking the beach whenever we want
🍽️ One of the best food cities in the country → 🌴 Dinner outside in January
🏙️ Big-city energy → 🤍 A life that doesn’t feel like we’re always rushing to the next thing
🏡 Being close to everything we knew → ✨ A completely different way of living
And that last one is probably the biggest.
Moving to Naples doesn’t mean you stop missing things about Chicago. We still do. But at some point, you realize you didn’t move here to recreate the life you left behind. You moved here because you were ready for something different.
If you’re considering moving to Naples and wondering what some of those trade-offs might look like for you, I created a free Naples Relocation Guide to help.
It includes neighborhood insights on some of Naples’ most popular areas, things to do, places to go, local favorites, and my take on the best of the best.
I’m Cheena Chandra, a Naples Real Estate Advisor specializing in waterfront homes and the coveted neighborhoods that match how you want to live.
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Cheena is focused on integrity, her customers' needs, and using technology and social media in innovative ways. She goes to great lengths for her customers and is committed to making the home buying and selling experience a seamless one. As a result, her customers have been amazing referrals for new business.