Moving From Chicago to Naples? 7 Surprising Things to Know

Chicago is one of the places my relocation buyers come from most often, and the first winter in Naples usually seals the decision. Moving from Chicago to Naples changes more than the weather: your state income tax goes away, homes are built differently, insurance matters more, and summer, not winter, becomes the season you plan around. Here are the seven things that surprise Chicago buyers most, so you can plan the move with clear eyes.

1. Your state income tax goes away

Illinois taxes personal income at a flat rate, and Florida has no personal state income tax at all. For a working household or a retiree drawing on savings, that difference shows up every year. Federal tax still applies, so time the move with your CPA. My guide to the Florida tax benefits every new Naples homeowner should know walks through it.

2. Property taxes work differently

Many Chicago buyers are used to some of the highest property tax bills in the country. In Florida, a homesteaded primary home gets up to $50,000 off its assessed value, and the Save Our Homes cap limits how fast that value can rise. File by March 1 once Naples is your permanent home. See my Collier homestead exemption guide.

3. Winter becomes your best season

No snow to shovel and no salt on the car. Naples winters are the reason the town fills up from November to April. The trade is summer: it is hot and humid, afternoon storms are common, and hurricane season runs from June 1 to November 30. Most of my Chicago buyers visit once in summer before they buy, which I recommend.

4. Homes are built differently

There are no basements here, because the water table sits close to the surface. Most homes are concrete block with impact windows and doors, and a covered lanai becomes your second living room. Storage moves to the garage and the attic, so plan the move with that in mind. My post on hurricane-ready homes in Naples shows what to look for.

5. Insurance and flood zones matter more

Homeowners insurance is a bigger line in the budget than most Chicago buyers expect, and the flood zone of a home can change the cost a lot. Get insurance quotes before you make an offer, not after. My Naples flood zones guide explains the zones in plain English.

6. Getting back to Chicago is easy

Southwest Florida International Airport in Fort Myers is a short drive from most of Naples and has nonstop flights to Chicago, so visits with family and friends stay simple. Many of my buyers keep ties to Chicago for the summer months and spend winters here.

7. Water views without the lakefront price

Chicago buyers love water, and Naples has more of it than people expect. In Golden Gate City, canal and lake homes come up at prices that surprise buyers used to lakefront Chicago. My post on Naples waterfront homes under $600K explains what that market looks like, and my Golden Gate City guide covers the neighborhood.

Featured home: 2998 52nd St SW

My listing at 2998 52nd St SW fits a lot of what Chicago buyers ask me for: new construction with water views, city water and no HOA, minutes from shopping, dining, healthcare and the major roads. Offered at $699,999:

• Built in 2024 with concrete block and impact windows and doors, on a 0.23-acre lot with canal and lake views
• Three bedrooms plus a den and two baths, about 1,695 square feet, in a split floor plan with cathedral ceilings
• A kitchen island open to the living and dining areas, and a primary bath with dual sinks and a walk-in shower
• A screened lanai, a fenced yard, a two-car garage and a dual paver driveway

See the photos and details on the 2998 52nd St SW listing page, or call me for a private showing or a video tour from Chicago.

How I help

I have helped families relocate to Naples since 2013, and I do a lot of it by video for buyers who are still up north. I can show you homes live, check insurance and flood zones before you fall for a house, and line up everything you need to make Florida your legal home after closing. Download my free Naples relocation guide to start, or read why so many buyers choose Naples.

Is it cheaper to live in Naples than Chicago?
It depends on the home and how you live. Florida has no state income tax and homesteaded homes get property tax protections, but homeowners insurance usually costs more. Compare the full monthly cost of a specific home, not just the price.

Are there basements in Naples homes?
Almost never. The water table is close to the surface, so homes are built on slabs, and storage moves to the garage and the attic.

Can I fly nonstop from Naples to Chicago?
Yes. Southwest Florida International Airport in Fort Myers has nonstop flights to Chicago and is a short drive from most of Naples.

When should I visit before moving?
Visit once in winter and once in summer if you can. Winter shows you the season everyone moves for, and summer shows you the heat and rain you will live with the rest of the year.

Ready to make the move? Search every home for sale in Naples, or call or text me at (239) 289-0749 for a video tour. Se habla español.