Moving from Chicago to Estero, Florida
Leave the 4.95% income tax and some of the highest property taxes in the country behind. Swap lake-effect winters for Gulf beaches 20 minutes away. Here is what changes and where Chicago buyers end up.
Chicago vs. Estero
| Chicago | Estero, FL | |
|---|---|---|
| State income tax | 4.95% flat | None |
| Property taxes | Among the highest effective rates in the U.S. | Homestead exemption up to $50,000, and assessed value increases capped at 3% a year |
| January weather | Wind chill, snow, highs around freezing | Highs in the mid 70s |
| Flights home | — | Nonstop RSW to O’Hare on American and United, and to Midway on Southwest |
| Lake life | Lake Michigan, five months a year | Lake communities and Gulf beaches all year |
Tax figures are general information for 2026, not tax advice. Talk to a CPA about your situation.
What changes when you buy in Florida
Most of it is good news. A few things are different from Illinois, and it pays to know them before you write an offer.
- File for homestead by March 1 after you close to get up to $50,000 off your assessed value and the 3% cap.
- Get an insurance quote before you sign. It can change a monthly payment more than the price does.
- Ask about CDD fees. Many newer communities have them, and they show up on your tax bill.
- Go newer. Homes built to the latest Florida building code often get better insurance rates.
- Season matters. January to April is busy. Summer often brings better builder incentives and less competition.
Communities to start with
Moving from Chicago? Get a plan, not a sales pitch.
Tell John your budget, timeline and must-haves. He will send back the communities that fit, a real monthly cost comparison with Chicago, and a short list of homes, then set up video tours if you cannot fly down yet.
- Side-by-side monthly budget
- 3 to 5 communities that fit
- Live video tours and remote closing
Moving from Chicago: questions
Is it cheaper to live in Estero than Chicago?
For most people, yes. Florida has no state income tax, and Illinois property taxes are among the highest in the country. Florida insurance and HOA fees can be higher, so John builds a side-by-side monthly budget before you buy.
How far is Estero from the airport?
Southwest Florida International Airport (RSW) is about 15 minutes from Estero, with nonstop flights to O’Hare on American and United and to Midway on Southwest.
Can I buy a home in Estero without flying down?
Yes. John does live video tours, e-signed contracts and remote closings with a Florida title company. Most buyers still make one trip to see their top picks in person.
Keep reading: Moving to Estero guide · Compare communities · Builder incentives