Fort Myers vs Chicago

Category / Metric	Fort Myers	Chicago
Financial Overview
Median Income	$61,894	$74,474
Unemployment Rate	4.2%	4.2%
Housing Market
Median Home Price	$385,000	$365,000
Price per SqFt	$217	$261
Monthly Rent (1BR)	$1,331	$1,507
Housing Cost Index	126.7	110.7
Cost of Living
Groceries Index	95.6	103.3
Gas Price (Gallon)	$2.60	$3.40
Safety & Lifestyle
Violent Crime (per 100k)	567.0	819.0
Bachelor's Degree+	34.9%	45.7%
Air Quality (AQI)	40	38

Chicago vs. Fort Myers: The Ultimate Head-to-Head Showdown

Alright, let's cut the fluff. You're standing at a crossroads between two completely different worlds. On one side, you have Chicago: the Windy City, a concrete jungle of deep-dish pizza, world-class museums, and brutal winters. On the other, you have Fort Myers: the sun-drenched gateway to Southwest Florida, where the biggest decision of the day is which beach to hit and whether to wear sandals or flip-flops.

Choosing isn't just about a zip code; it's a lifestyle declaration. Are you chasing the energy of a global metropolis or the tranquility of coastal living? We're going to break this down with hard data, but we're also going to talk straight about what it feels like to live in each place. Grab a coffee (or a frosty beverage)—let's get into it.

The Vibe Check: Fast-Paced Metro vs. Laid-Back Beach Town

Chicago is a heavyweight contender. It's the third-largest city in the U.S., and it carries itself with the confidence of a place that has everything. The vibe is gritty, ambitious, and culturally rich. You've got 77 distinct neighborhoods, each with its own personality. From the high-rises of the Loop to the historic brownstones of Lincoln Park, the city pulses with an energy that's hard to find elsewhere. It's a city for the hustlers, the artists, the foodies, and the sports fans. If you crave four distinct seasons, a deep arts scene, and the feeling of being in the center of the action, Chicago calls your name.

Fort Myers, by contrast, is the definition of chill. It's a mid-sized city (about 100,000 people) that feels more like a large town. The pace is slower. The focus is outdoors: boating, fishing, golfing, and beachcombing. The culture is a blend of year-round residents and a massive seasonal population of "snowbirds" who flock down for the winter. It's a haven for retirees, but it's also attracting young families and remote workers who trade cubicles for kayaks. The vibe is friendly, unpretentious, and deeply connected to the water and sun.

Who is it for?

• Chicago is for the career-driven, culturally curious, and weather-tolerant. It's for those who want access to major league sports, Michelin-starred dining, and a skyline that takes your breath away. You have to be okay with the hustle and the cold.
• Fort Myers is for the outdoorsy, relaxed, and sun-seeking. It's for retirees looking to enjoy their golden years, families who prioritize outdoor activities, and remote workers who can trade a high cost of living for a higher quality of life. You have to be okay with heat, humidity, and a quieter social scene.

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The Dollar Power: Where Does Your Salary Actually Go?

This is where the data starts to get interesting. At first glance, the numbers seem counterintuitive. Fort Myers has a lower median income, but its housing is more expensive? Let's unpack "purchasing power"—the real-world value of your money.

Salary Wars: If you earn $100,000 in Chicago, your take-home pay after federal, state, and city taxes will be significantly less than in Fort Myers. Chicago has a city income tax of 1% and Illinois has a flat state income tax of 4.95%. Florida, however, has no state income tax. This is a massive deal. That $100k salary in Fort Myers keeps more money in your pocket from the get-go. But, as we'll see, housing costs can eat into that advantage.

TABLE: Cost of Living Breakdown

Category	Chicago	Fort Myers	The Lowdown
Median Home Price	$365,000	$385,000	Fort Myers is slightly more expensive to buy, which is a shocker for many. The Florida market has been red-hot.
Rent (1BR)	$1,507	$1,331	Chicago rent is higher, but the gap is narrower than you'd expect given the city size difference.
Housing Index	110.7	126.7	This index (where 100 is the national average) confirms Fort Myers' housing is more expensive relative to the U.S. average.
Median Income	$74,474	$61,894	Chicagoans earn more on paper, but after taxes and housing, the playing field levels.
Utilities	Higher (Heating)	Lower (Cooling)	This flip-flops by season. Chicago's heating bills in winter are steep; Fort Myers' AC costs in summer are brutal.
Groceries	Slightly Higher	Slightly Lower	Negligible difference. Both are near the national average.

The Verdict on Money: It's a near draw, but with a twist. Fort Myers wins on tax savings, but Chicago offers more diverse housing options. In Chicago, you can find a cheaper apartment in a less trendy neighborhood. In Fort Myers, the housing market has been squeezed by demand from retirees and remote workers. For a $100k earner, your money might stretch slightly further in Fort Myers if you can find affordable housing. But if you need a specific type of home in a specific area, Chicago's vast inventory gives you more leverage. The "sticker shock" is real in both, but for different reasons.

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The Housing Market: Buy, Rent, or Run?

Chicago (Buyer's Market? Sort Of.)
The Chicago housing market is competitive but nuanced. The median price of $365,000 is misleading because it averages out huge variation. A downtown condo could be $600k+, while a single-family home in a neighborhood like Rogers Park might be $300k. The market is generally more balanced than Fort Myers. You have room to negotiate, especially in the suburbs. The big challenge here isn't just price, but property taxes. Cook County has some of the highest property taxes in the nation, which can add $8,000-$10,000+ annually to the cost of a $365k home. This is a major hidden cost.

Fort Myers (Seller's Market, Plain and Simple.)
Fort Myers' housing index of 126.7 tells the story. The market is tight and competitive. The pandemic and the rise of remote work sent a wave of buyers to Florida, driving prices up. Finding a home at the median price of $385,000 can be a challenge. Bidding wars, while not as frenzied as 2021, are still common. Renting is also competitive due to the seasonal influx. The advantage? No state income tax and lower property taxes than Illinois. However, homeowners insurance in Florida is skyrocketing due to hurricane risk—this can add $3,000-$6,000+ annually to your cost of ownership.

The Dealbreaker: In Chicago, you pay more in taxes. In Fort Myers, you pay more in insurance and compete harder for a home. It's a pick-your-poison scenario.

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The Dealbreakers: Weather, Traffic, and Safety

Weather: The Ultimate Divider
This isn't a close call; it's a chasm.

• Chicago: The data says 21.0°F, but that's just the January average. The reality is brutal winters with sub-zero wind chills, heavy snow, and gray skies for months. Summers are glorious but can be humid. You need a serious wardrobe investment: heavy coats, boots, layers. The weather can be a mental and physical grind.
• Fort Myers: The data says 72.0°F, but that's the annual average. The reality is sweltering, humid summers (regularly 90°F+ with "feels like" temps over 100°F) and a hurricane season (June-Nov) that requires preparedness. Winters are sublime. If you hate being cold, this is paradise. If you hate being sweaty, this is hell.

Verdict: If you can't handle cold, Fort Myers wins. If you can't handle heat and humidity, Chicago wins.

Traffic & Commute

• Chicago: Challenging. The "L" train system is extensive and a lifesaver, but driving is a nightmare. The Kennedy and Dan Ryan expressways are legendary for gridlock. Commute times average 30-45 minutes. Parking is expensive and scarce.
• Fort Myers: Manageable. Traffic is mostly congestion on major arteries like I-75 and US-41, especially during peak tourist/snowbird season. Commutes are generally shorter. It's a car-dependent city, but you won't spend hours in standstill traffic.

Verdict: Fort Myers is far easier for drivers.

Crime & Safety
Let's be direct. Chicago's violent crime rate of 819.0/100k is high. It's a national talking point for a reason. However, this is heavily concentrated in specific neighborhoods. Areas like Lincoln Park, Lakeview, and the North Shore are very safe. It's a city of stark contrasts. Fort Myers' rate of 567.0/100k is also above the national average but lower than Chicago's. Like any city, there are safer and less safe pockets. Generally, Fort Myers feels safer day-to-day, especially in suburban areas.

Verdict: Fort Myers is statistically safer and feels safer for most residents.

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The Final Verdict: Who Wins Your Move?

This isn't about declaring one city "better." It's about which city is better for you. Here’s our expert breakdown.

Winner Category	City	Why It Wins
Families	Chicago	The public school system (while challenging) has incredible magnet and selective enrollment options. The cultural and educational institutions (museums, zoo, parks) are world-class and provide endless enrichment. The trade-off is weather and cost.
Singles / Young Pros	Chicago	The sheer volume of networking events, social scenes, career opportunities, and nightlife is unmatched. You can find your tribe in any of the 77 neighborhoods. Fort Myers' social scene is quieter and more family/retiree-oriented.
Retirees	Fort Myers	The no-income-tax benefit is huge on a fixed income. The lifestyle is built for relaxation and outdoor activity. The weather is a primary draw. Chicago's vibrant arts scene is a plus, but the winters are a major drawback for this demographic.

Chicago: Pros & Cons

Pros:

• Unbeatable cultural and culinary scene.
• Robust public transit (if you avoid driving).
• Powerful job market across diverse industries.
• Four distinct seasons, with gorgeous summers.
• Deep neighborhood character and global city feel.

Cons:

• Brutal, long winters.
• High cost of living, especially property taxes.
• Traffic and parking headaches.
• Significant crime, heavily dependent on neighborhood.
• City income tax and high overall tax burden.

Fort Myers: Pros & Cons

Pros:

• No state income tax.
• Fantastic weather (for those who love the sun).
• Slower, more relaxed pace of life.
• Proximity to Gulf Coast beaches and nature.
• Generally lower traffic and easier commutes.

Cons:

• Scorching, humid summers.
• Competitive and expensive housing market.
• Hurricane risk and high insurance costs.
• Limited public transit; car is a must.
• Fewer major corporate HQs and niche cultural scenes.

The Bottom Line

Choose Chicago if you're chasing a career, crave urban energy, and can handle the cold. It's a city that will challenge you and reward you in equal measure.

Choose Fort Myers if you're prioritizing lifestyle over hustle, love the sun, and are ready for a slower, more nature-focused existence. It's a place to live, not just work.

Your move.