Moving to Naples from Chicago usually starts as a second home and turns into a bigger decision: whether to keep Illinois as your domicile or make Florida your permanent home. Naples is served by Southwest Florida International Airport (RSW), whose September 2026 update lists nonstop service to both O’Hare and Midway, and Florida does not levy a personal income tax, but changing your domicile is a legal step with rules in both states, so it deserves a plan before it deserves a moving truck.
I am Joe Belz, a Broker Associate at Compass and the lead agent of Joe Belz + Apex Team. I moved to Naples in 1980 and I have been in the Naples market since 1990. Chicagoland is my top feeder market, and the Midwest as a whole, the people I call the I-75 crowd, is my biggest source of buyers. About 70 percent of my buyers are second-home buyers, and many of them go on to make Naples their primary residence for tax purposes, even though they are not here year round.
Getting from Chicago to Naples
Flying into RSW
Naples is served by Southwest Florida International Airport, known by its code RSW, which is located in Fort Myers. The airport describes its location as having quick access to Interstate 75 and U.S. 41, and U.S. 41 is the same road that gives “west of 41” its name. The airport’s September 2026 Air Service Update lists nonstop service to both Chicago-O’Hare (ORD) and Chicago-Midway (MDW), among more than 80 nonstop destinations served by 15 airlines.
Service changes with the season. Before you plan a closing or a walkthrough around a particular flight, check the airport’s current nonstop list and your airline’s schedule.
Driving down I-75
There is a reason I call the Midwest the I-75 crowd. The route you take out of Chicagoland changes the mileage and the drive time. Map your own route from your own driveway before you decide whether driving fits how you want to use the house.
Second home or Florida domicile: the decision that shapes everything else
The Florida rules can be explained and verified. What you will owe, whether you qualify for anything and how Illinois will treat you are questions for a tax professional. Illinois has its own residency rules, and you need a tax professional who works in both states before you change anything.
Here is how the Florida side works.
Florida has no state personal income tax
Article VII, Section 5 of the Florida Constitution provides that no tax upon the income of natural persons who are residents or citizens of the state shall be levied by the state in excess of the amounts that may be credited against or deducted from a similar tax levied by the United States or any state. The Florida Department of Revenue puts it more simply in its guide for new residents: Florida does not impose personal income tax, inheritance tax, gift taxes, or tax on intangible personal property. Florida residents may still pay other state and local taxes and fees, including sales tax and property tax.
Declaring domicile in Collier County
Florida Statutes section 222.17 allows a person who has established a domicile in Florida to manifest and evidence it by filing a sworn statement with the clerk of the circuit court in the county where they reside. For someone who keeps another home in another state, the statute provides for a sworn statement that the Florida home is their predominant and principal home and that they intend to continue it permanently as such. The statement also lists where you formerly resided and any other places of abode you maintain.
In Collier County, that filing is made with the Clerk of the Circuit Court and Comptroller. The Clerk’s Declaration of Domicile form states that it is filed in accordance with section 222.17, and it is sworn to before a deputy clerk or a Florida notary, by physical presence or online notarization. The same form has a second section for people domiciled in another state who want to record that they intend to keep that domicile despite owning a Florida home. That option matters for Chicago-area owners who plan to stay Illinois residents.
The Florida Department of Revenue explains the weight of each step: filing a declaration of domicile, qualifying for homestead exemption, or registering to vote in Florida can establish residency, while other actions, such as obtaining a Florida driver license, only indicate an intent to establish residency. A declaration is a statement of intent under oath. It is not a tax plan, and it does not by itself settle anything with Illinois.
The homestead exemption
Florida Statutes section 196.031 grants a homestead exemption to a person who, on January 1, holds legal or beneficial title to Florida real property and in good faith makes it their permanent residence. The Collier County Property Appraiser describes the exemption as a reduction of up to 25,000 dollars from the assessed value for all taxing authorities, plus an additional exemption on the assessed value above 50,000 dollars for all levies except school district levies. Amendment 3, which voters approved on November 3, 2026, raises the exemption for all non-school taxes to 150,000 dollars in 2027 and 250,000 dollars in 2028. If you are not a Florida resident on December 31, 2026, you receive the existing exemption when you qualify and the larger one beginning with your fifth year of exemption.
The timing is where out-of-state buyers get caught. Florida Statutes section 196.011 sets the filing deadline at March 1. The Collier County Property Appraiser states that you must be a Florida permanent resident as of January 1, and that new applications for the current year must be made in person prior to March 1. Among the documents it lists are evidence of ownership, a Florida driver license and a Florida vehicle registration dated before January 1, and Collier County voter registration dated before January 1 if you vote. It lists a Declaration of Domicile filed with the Clerk before January 1 as an optional document.
Save Our Homes and portability
Once a home carries the homestead exemption, Article VII, Section 4 of the Florida Constitution limits how fast its assessed value can rise. Annual changes may not exceed the lower of 3 percent of the prior year’s assessment or the percent change in the Consumer Price Index. The Collier County Property Appraiser notes that the cap takes effect the year after the homestead exemption is granted, and that when a homesteaded property is sold, its assessed value becomes full market value for the new owner.
Portability is the part people ask about when they plan to move within Florida later. The Constitution allows a person who establishes a new homestead, and who held a homestead exemption as of January 1 of any of the three years before, to have the new homestead assessed at less than just value, transferring up to 500,000 dollars of the accumulated difference. The Property Appraiser reminds owners that a new homestead application is required at the new residence; nothing transfers automatically.
These rules change how the numbers on a Naples home behave over time. The Property Appraiser decides who qualifies.
If you keep Naples as a second home
A second home that is not your permanent residence does not get the homestead exemption, but it has a different protection. Under Article VII, Section 4(g) of the Florida Constitution, assessments of non-homestead residential property with nine units or fewer may not increase more than 10 percent a year, for all levies other than school district levies, and the property is reassessed at just value after a change of ownership. Under Amendment 3, that cap drops to 5 percent beginning January 1, 2027. That difference is a reason to decide early which way you are leaning.
Amendment 3 passed on November 3, 2026
Florida voters approved Amendment 3 on November 3, 2026, clearing the 60 percent approval the Florida Constitution requires. The Florida Legislature placed it on the ballot in June 2026 as House Joint Resolution 1-F, titled “Increased Homestead Exemption; Lower Cap on Increases in Non-Homestead Property Assessments,” and it takes effect January 1, 2027. According to the ballot summary published by the Florida Division of Elections, it increases the homestead exemption for all non-school taxes to 150,000 dollars in 2027 and 250,000 dollars in 2028, and adjusts for inflation after that. People who are not Florida residents on December 31, 2026 receive the existing homestead exemption upon qualifying, with the increased exemption beginning with the fifth year of exemption, to the extent permitted by the U.S. Constitution. Among its other provisions, it reduces the annual cap on assessment increases for non-homestead properties from 10 percent to 5 percent. If you are weighing a change of domicile around the December 31, 2026 date, or plan to keep Naples as a second home, raise it with your tax professional now.
What a seasonal home costs to carry
A Naples home that you use part of the year is still a full-time house, and the list of carrying costs is longer than the mortgage and the tax bill. The dollar figures depend on the property, so get real numbers for the homes you are actually considering.
| Cost | What drives it | What to ask before you buy |
|---|---|---|
| Property tax | The Property Appraiser’s assessment each year, the exemptions you qualify for, and the homestead or non-homestead assessment limit. The Department of Revenue notes that property taxes are collected annually by the county tax collector. | What is the current assessed value, what exemptions does the seller have, and what happens to the assessment after the sale resets it? |
| Insurance | Wind and flood exposure, the home’s elevation and construction, roof age and openings protection. | What is the first floor elevation, did this home get water, and what would it cost to insure it the way I want it insured? |
| Association and club dues | Whether the home is in an association, the association’s reserves and plans, and whether you join a private club. | How is the association’s financial health, are special assessments planned, and is there a waitlist or initiation fee at the club I want? |
| Maintenance while you are away | Air conditioning and humidity control, pool, landscaping, pest control and storm preparation. | Does the home have a generator, how old are the systems, and who will check them while I am in Chicago? |
| Home watch | How often the house is checked, what is checked, and who responds when something goes wrong. | Who has a key, who gets the call, and how will I hear about it? |
My buyers ask about insurance costs, whether a home got water, the first floor elevation, generators, the association’s financial health, special assessments, and club waitlists and fees. Water and elevation get their own guide: first floor elevation, flood zones and insurance for Naples homes, and the association and inspection questions are covered in Naples home buyer due diligence: questions to ask before you make an offer.
Starting from Chicago?
Tell me how you plan to use a Naples home, how often you will be here and which way you are leaning on domicile. We can sort the neighborhoods and the carrying costs before you book a flight.
Contact JoeThe Naples season and the Naples summer
Most people picture Naples in the winter, and that is when the town is at its fullest: restaurants booked, the beaches busy, Fifth Avenue South and Third Street South lively at night. The National Weather Service office in Miami, whose reporting sites include Naples Municipal Airport, describes southeast Florida as having two predominant seasons. Its winter season has cooler temperatures, lower humidity and less frequent rain, and it takes in what the rest of the country would call autumn and spring.
The summer is a different place, and anyone buying a home here should see it at least once. The same NWS study, built on Miami International Airport records from 1956 through 1997, found a median start of the summer season on May 21 and a median end on October 17. It describes daily lows that rarely fall below 70 degrees, dew points in the lower to middle 70s, and showers and thunderstorms as an almost daily occurrence. The National Hurricane Center states that the Atlantic hurricane season runs from June 1 to November 30, with most activity between mid-August and mid-October.
In daily life, summer mornings and evenings are for the beach and the water, and afternoon storms shape the schedule. For a seasonal owner, summer is exactly when the house is empty and working hardest: the air conditioning is running constantly to control humidity, and storm season overlaps with the months you are most likely to be in Chicago. That is why the maintenance and home watch rows in the table above are not optional.
Choosing where to live west of 41
One of the things buyers get wrong is thinking Naples is a small town. I like to think of it as one, but it is not. Figuring out what part of town you want to live in is critical, and four things help decide it: what you want to walk to, whether you want to be on the water, which club you want to belong to, and the house itself. I write more about the misconceptions I hear in what people get wrong about Naples real estate.
By what you want to walk to
If you want to walk to dinner and walk to the beach, start with Olde Naples. It puts you close to Fifth Avenue South, Third Street South and the Naples Pier, with streets of single-family homes, many of them newer construction on older lots, a short walk from the Gulf beach. If you want a quieter street close to the beach, the Moorings and Coquina Sands sit just north. Farther north, Park Shore puts Venetian Village, with its shops and waterfront dining, within reach, and mixes canal-front single-family homes with Gulf-front condominium towers. Pelican Bay, farther north again, is a planned community with its own 27-hole golf course and a range of single-family homes and condominiums.
Cruising Naples Episode 7 follows the Naples beaches from sunrise to sunset, from Port Royal to Bay Colony, with beachfront dining along the way.
By water access
If a boat is part of the plan, the question becomes how you want to reach open water. Port Royal, Aqualane Shores, Royal Harbor, the Moorings, Park Shore and Vanderbilt Beach all have waterfront homes, and each one’s canals, bridges and routes to the Gulf are different. Start with the boat you own or want, and then which waterfront fits it. If you want to see the water first, my on the water page lists fishing charters, sunset cruises and paddleboard tours.
By the club you want
Most of my clients are golfers, and they live where they want and drive to a private golf club, so we help people navigate which club and then where to live. I belong to Olde Florida and Jozef Maston on our team is a member of Hideout, and both are golf clubs, not communities. Initiation fees, dues and waitlists are in Naples golf clubs compared, and the Apex Team Golf Club Quiz is on our golf courses page.
By the house itself
West of 41, many single-family homes are either newer construction or older homes on lots that buyers consider rebuilding. I started in this business in new construction, and I explain what building from scratch involves, and how long it takes, in New Construction in Naples West of 41. You can browse every area I cover on my neighborhoods page.
How I work with out-of-town clients
My approach to out-of-town clients comes down to relationships, including at the restaurants and private clubs in town.
A client of mine who has lived here full time for years was out of town when their air conditioning went out. They called me. I scheduled the AC contractor, met them at the house and got it fixed.
My years as a developer mean I can give insights on construction costs for new homes or remodeling, zoning and permitting, and two of my closest friends are a Naples architect and a luxury home builder.
People call me when they are in town and every restaurant is booked, because I can get them a reservation.
You can read more about how I work with buyers on my buyers page, and more about my background in Joe Belz, Naples real estate broker at Compass.
A short checklist for Chicago-area buyers
- Decide whether this is a second home or a future Florida domicile, and talk to a tax professional who works in Illinois and Florida before you change anything.
- If you plan to claim homestead, note January 1 and the March 1 filing deadline, and gather the documents it lists.
- See Naples at least once between late May and October before you commit.
- Get real numbers for property tax, insurance, association and club dues, maintenance and home watch on the specific homes you like.
Frequently asked questions
Naples is served by Southwest Florida International Airport (RSW) in Fort Myers. The airport’s September 2026 Air Service Update lists nonstop service to both Chicago-O’Hare (ORD) and Chicago-Midway (MDW). Airline schedules change by season, so check the airport’s current nonstop list and your airline before you plan a trip around a specific flight.
Florida does not levy a personal income tax. Article VII, Section 5 of the Florida Constitution limits the state’s ability to tax the income of natural persons, and the Florida Department of Revenue states that Florida does not impose personal income tax, inheritance tax, gift taxes or tax on intangible personal property. Whether you are treated as a Florida resident, and what your former state expects from you, is a separate question for a tax professional.
Florida Statutes section 222.17 lets a person who has established a Florida domicile file a sworn Declaration of Domicile with the clerk of the circuit court in the county where they reside. In Collier County that is the Clerk of the Circuit Court and Comptroller, whose form is sworn before a deputy clerk or a notary. The Florida Department of Revenue says filing a declaration of domicile, qualifying for homestead exemption or registering to vote can establish residency, while a Florida driver license only indicates intent. Talk to a tax professional before you file.
Florida Statutes section 196.011 sets the homestead filing deadline at March 1. The Collier County Property Appraiser states that new applications for the current year must be made in person prior to March 1, and that the applicant must be a Florida permanent resident as of January 1. The Property Appraiser lists a Florida driver license and Florida vehicle registration dated before January 1 among the required documents, with a Declaration of Domicile filed before January 1 as an optional document. Check the Property Appraiser’s site for current filing options.
No. Under Florida Statutes section 196.031, the homestead exemption applies to property a person owns on January 1 and in good faith makes their permanent residence. A second home that is not your permanent residence does not qualify. Non-homestead residential property has its own annual assessment limit under Article VII, Section 4(g) of the Florida Constitution: increases may not exceed 10 percent a year for levies other than school district levies. Amendment 3, which Florida voters approved on November 3, 2026, lowers that cap to 5 percent beginning January 1, 2027.
Save Our Homes is the assessment limitation in Article VII, Section 4 of the Florida Constitution. Once a home receives the homestead exemption, annual increases in its assessed value are limited to the lower of 3 percent or the change in the Consumer Price Index, starting the year after the exemption is granted. The assessed value resets to just value after a change of ownership. Portability can let an owner transfer up to 500,000 dollars of that accumulated difference to a new homestead within the window the Constitution sets.
The National Hurricane Center states that the Atlantic hurricane season runs from June 1 to November 30, with the climatological peak on September 10 and most activity between mid-August and mid-October. Naples is on Florida’s Gulf coast, inside that basin. If you own a seasonal home, plan who will prepare and check the house in those months while you are away.
Related resources
Thinking about Naples from Chicago? Let’s talk
Whether you are planning a first season, weighing a change of domicile or ready to look at homes, the first conversation is about how you want to use Naples and where your days would run. No obligation.
Contact JoeSources
- Southwest Florida International Airport, Air Service Update, September 2026, and About RSW, flylcpa.com
- Florida Constitution, Article VII, Sections 4 and 5, and Article XI, Section 5, flsenate.gov
- Florida Statutes, section 222.17 (Manifesting and evidencing domicile in Florida), section 196.031 (Exemption of homesteads) and section 196.011 (Annual application required for exemption), 2026 Florida Statutes, leg.state.fl.us and flsenate.gov
- Florida Department of Revenue, Tax Information for New Residents (GT-800025, R. 08/25), floridarevenue.com
- Collier County Clerk of the Circuit Court and Comptroller, Declaration of Domicile form (rev. 2025-08-20), collierclerk.com
- Collier County Property Appraiser, Homestead Exemption, and Save Our Homes and Portability, collierappraiser.com
- Florida Division of Elections, Initiatives database, Amendment 3 (ballot title and summary), dos.fl.gov
- Bay News 9, “Florida voters approve Amendment 3, providing property tax relief for homeowners,” November 4, 2026, baynews9.com
- The Florida Legislature, CS/HJR 1-F enrolled text, bill history and staff analysis, flsenate.gov
- National Weather Service Miami, Duration of Summer Season in South Florida, and Mid-Rainy Season 2025 Update, weather.gov
- National Hurricane Center, Tropical Cyclone Climatology, nhc.noaa.gov
Rates, rules and dates are as published by each source on October 30, 2026, and the Amendment 3 result as reported on November 4, 2026. Tax law, exemption amounts, filing requirements and flight service change. This guide is general information about moving to and buying a home in Naples and is not legal, tax, insurance or financial advice. Illinois and Florida each apply their own residency rules. Confirm anything specific to your property, your residency or your circumstances with a tax professional licensed to advise in both states, with the Collier County Property Appraiser and Clerk, and with the relevant insurance and legal professionals.
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