8 Things You Need to Know Before Moving to Naples from Chicago

As temperatures drop and you brace yourself for another Chicago winter, it’s no surprise your thoughts are drifting to sunnier horizons. With beautiful weather year-round, a fast-growing job market, and a high quality of life, Naples, Florida is an irresistible place to live and raise a family. However, before you dive in and start traveling south, you have to ask yourself, “What can I expect when moving to Naples from Chicago?”

We’re here to help. Naples Relocation Experts are the Paradise Coast’s premier moving consultation service. We’ve helped hundreds of families make themselves at home in Naples, Florida (including several Chicagoans). We go beyond basic real estate services and use our local expertise to help you fully acclimate to our community. Starting now!

Keep reading to learn eight things you need to know before moving to Naples, Florida from Chicago, Illinois.

1. Is Naples, FL a better place to live than Chicago?

A downtown Chicago bridge with the buildings in the background
A bridge in downtown Chicago

Our team may be experts on everything that makes Naples an incredible place to live, but you don’t need to just take our word for it. There’s a reason that the Naples, Florida Metro Area ranked highest in well-being in the US four straight years in a row. The Well-Being Index score evaluates career, social, financial, community, and physical elements, so you can be sure Naples has everything you need to build a happier, more successful life.

Naples was also named as one of Travel + Leisure Magazine’s Best Places to Move To, and ranks #12 in U.S. News & World Report’s Best Places to Live and #2 in Best Places to Retire. In comparison, Chicago ranks #79 in Best Places to Live and #87 in Best Places to Retire.

What exactly makes Naples a better place to live than Chicago? When determining the “Best Places to Live,” the rankings consider:

  • The strength of the area’s job market, including unemployment rate and average salary
  • How comfortably the average resident can afford to live within their means
  • How satisfied residents are with their daily lives
  • The “desirability” of the area and whether people want to live there
  • Whether people are moving to or away from the area

We’ll discuss more about the differences in the quality of life, job market, and cost of living later in this article. For now, if you’re moving to Naples from Chicago, you’re going up 67 ranks on your way to a better place to live!

2. Does Naples, FL have a better quality of life?

Kayaking in Pelican Bay
Kayaking in the bay near Pelican Bay in Naples, FL

You bet it does! The Quality of Life index score for Naples is 10% higher than Chicago. Naples, Florida even ranks #4 in Best Places to Live for Quality of Life. To truly appreciate the better quality of life that Naples has to offer, let’s break down what “quality of life” actually means.

U.S. News & World Report’s Quality of Life index evaluates:

  • Crime Rates
  • Quality and Availability of Health Care
  • Quality of Education
  • Well-Being
  • Average Commute Time
  • Air Quality

As someone who values your family’s safety, happiness, and health, it’s easy to see the benefits of the high quality environment Naples has to offer.

3. Are there more job opportunities in Naples, FL?

Career success is always an important factor to consider when relocating. Will you be able to easily find a job in this new city? Are you able to grow and continue your professional development? Is there long-term job security for yourself, your partner, and your children?

Finding a job in Naples that you’re happy with and can support your family is easier than ever. Naples’ job growth is currently trending positively and the job market is predicted to grow 39.3% over the next ten years. Job growth in Chicago is currently negative and only predicted to grow 25.6% in the next decade. That means Naples’ long-term job market growth is 13.7% higher than Chicago’s!

In other words, there’s no need to worry about job availability when moving to Naples from Chicago. Our already thriving job market will only continue to grow.

4. Is Naples, FL a safer place to live than Chicago?

Mercato Shops Naples
Mercato Shops in Naples, Florida

It’s an absolute essential that you feel safe in the place you call home – especially when you’re looking to relocate your family.

Lucky for us and everyone in our community, Naples, Florida is an extremely safe place to live. In fact, we’re ranked #1 in U.S. News & World Report’s Safest Places to Live! According to the FBI’s crime reports on murder, violent crime, and property crime rates, Naples is the safest place to call home in all of the United States.

When comparing the safety of Naples versus Chicago, the Crime Index score for Naples is 12.9% higher than Chicago. Sources also cite Chicago as having:

  • 67% more total crime than the national average
  • 143% more violent crime than the national average
  • 52% more property crime than the national average

To learn more about safety in Naples, Florida compared to Chicago, check out our article “Is Naples Safe Compared to Chicago?

5. What is the cost of living in Naples, FL?

Both Naples and Chicago are lively cities with plenty of activities for date nights and family nights alike. That’s why it’s so important for any resident to consider potential expenses when budgeting for daily life and leisure.

Anyone relocating to Naples from Chicago can expect a slightly higher cost of living. When comparing the two locations, living in Naples is 4.7% more expensive overall than living in Chicago. Statistics show that expenses are higher in Naples for food and groceries, health-related expenses, housing, and utilities. However, transportation costs are 41.8% less expensive than Chicago.

If you’re looking for a real-life example, the average cost for a bottle of water is $1.93 in Naples and $1.78 in Chicago, while the US average is $1.63.

Overall, the difference in cost of living between Naples and Chicago is relatively small. In our expert opinion, it’s worth it for all of the other benefits Naples, Florida has to offer!

6. Will my children receive a better education in Naples, FL?

A common question for any relocating family is the quality of a city’s school district. We want to ensure we’re setting our children up for long-term success with quality education and care. So, how does education in Naples compare to Chicago?

For starters, Naples has smaller, more intimate classroom settings to provide your child with more personalized attention. The student-teacher ratio in Naples is 24:1, while the student-teacher ratio in Chicago is 199:1 – a 729% difference. Children in Naples have a much better opportunity to connect with and spend much-needed time with their teachers.

Naples is a great place to be for college-bound students. According to the College Readiness Index, Naples scores 8.4% higher for college readiness than Chicago. Nine of our local high schools are also recognized on U.S. News & World Report’s Best High Schools rankings.

You can learn more by reading our article, “Finding Good Childcare in Naples.

We’d love to go in-depth with you on how your children can benefit from moving to Naples from Chicago. Just give us a call to book an appointment and one of our relocation experts will speak with you directly.

7. What is transportation like in Naples, FL?

A Cruiser Bike in Downtown Naples
A bike in Downtown Naples

It’s hard to beat the walkability of Chicago. With an easily traveled downtown, several great neighborhoods, and a Walk Score of 77, Chicago is the fourth most walkable large city in the US. In comparison, Naples has a Walk Score of 35. That said, there are several areas of Naples with beautiful scenery that are great for a stroll. Naples residents report the downtown area as highly walkable and neighborhoods like Old Naples, Lake Park, and Sun Terrace score high for walkability.

The average commute time in Naples (25.4 minutes) is also 6.4 minutes shorter than Chicago (31.8 minutes). This is largely due to traffic differences and the fact that a higher percentage of Chicagoans use public transportation on their commute. Here’s how transportation methods vary in the two cities:

  • Driving: 86.1% in Naples vs. 76.1% in Chicago
  • Public Transit: 1.1% in Naples vs. 11.3% in Chicago
  • Walking or Biking: 1.9% in Naples vs. 3.5% in Chicago

It’s also important to remember the statistic we mentioned when discussing cost of living: Transportation costs are 41.8% less expensive in Naples than Chicago!

Overall, when moving to Naples from Chicago, you can expect to drive more compared to taking public transportation or walking. However, when the mood strikes for an after-dinner stroll, Naples will have plenty of scenic neighborhoods to choose from.

8. What is the weather like in Naples, FL?

The naples pier and beach
Naples Pier in Naples, Florida

This is an easy one, and likely one of the many reasons you’re considering moving to Naples from Chicago! One of the best things about living in sunny Southwest Florida is our year-round beautiful weather.

Here is what you can expect from the weather in Naples:

  • The hot season lasts for 4.5 months, from May 23 to October 6, with an average daily high temperature above 86°F.
  • The cool season lasts for 2.8 months, from December 9 to March 4, with an average daily high temperature below 77°F.
  • 264 sunny days per year on average.

This is what you’re currently experiencing for weather in Chicago:

  • The warm season lasts for 3.6 months, from June 3 to September 20, with an average daily high temperature above 73°F.
  • The cold season lasts for 3.2 months, from December 2 to March 9, with an average daily high temperature below 43°F.
  • 189 sunny days per year on average.

Overall, Naples has consistent warmer temperatures, 39.6% more sunny days each year, and, most importantly, NO SNOW!

So, Should I Move to Naples from Chicago?

Let’s rephrase the question: Do you want a better quality of life? Would you benefit from long-term job security? Are you interested in living in the safest city in the US? Should your children receive a better, more intimate education? Do you want warm, sunny days year-round?
If you answered yes to any of the above questions, it sounds like Naples, Florida is the perfect fit for your family. When you’re ready to start the process of moving from Naples to Chicago, contact and book an appointment with Naples Relocation Experts. We’ll use our local knowledge and real estate expertise to help your family easily settle into your new home.

Drew Josephson
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