Westerly CDP vs Chicago

Category / Metric	Westerly CDP	Chicago
Financial Overview
Median Income	$82,333	$74,474
Unemployment Rate	4.3%	4.2%
Housing Market
Median Home Price	$400,200	$365,000
Price per SqFt	$null	$261
Monthly Rent (1BR)	$1,362	$1,507
Housing Cost Index	98.9	110.7
Cost of Living
Groceries Index	97.0	103.3
Gas Price (Gallon)	$3.40	$3.40
Safety & Lifestyle
Violent Crime (per 100k)	159.5	819.0
Bachelor's Degree+	38%	45.7%
Air Quality (AQI)	34	38

Chicago vs. Westerly CDP: The Ultimate Head-to-Head Showdown

Choosing between Chicago and Westerly, Rhode Island, is like picking between a roaring rock concert and a quiet bonfire on the beach. One is a global powerhouse of culture, commerce, and chaos; the other is a charming coastal enclave where the rhythm is set by the tides. If you're standing at this crossroads, you're not just choosing a zip code—you're choosing a lifestyle.

Let's cut through the noise. As a relocation expert, I’ve seen people chase the "big city dream" only to burn out, and I’ve watched others seek small-town peace just to feel bored. We’re going to dig into the data, the dollar signs, and the day-to-day realities to find out which of these two vastly different locales is your perfect fit.

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

Chicago is the quintessential "Second City" that often feels like the first. It’s a place of towering skyscrapers, deep-dish pizza, and world-class museums. The energy is relentless. You have 2.6 million neighbors, each with their own hustle. The culture is a melting pot of neighborhoods, from the artsy vibes of Wicker Park to the historic elegance of the Gold Coast. It’s a city for people who crave options—endless dining, 24/7 transit, and a skyline that commands respect. But it’s also a city of grit. The winters are brutal, the traffic is legendary, and the cost of living, while manageable compared to NYC, has its own sting.

Westerly CDP (Census Designated Place) in Rhode Island is the polar opposite. With a population hovering around 18,500, it’s a tight-knit community where the main attractions are the stunning beaches—like Misquamicut—and a historic downtown. Life here moves at a gentler pace. It’s about weekend farmers' markets, kayaking in the salt ponds, and enjoying a sunset over the Atlantic. Westerly is for those who want to escape the concrete jungle, value a strong sense of community, and prioritize nature over nightlife. It’s a haven for retirees, families wanting a safe environment, and anyone who believes a good day ends with sand between their toes.

Who is each city for?

• Chicago: Ambitious young professionals, culture vultures, foodies, and anyone who needs the anonymity and stimulation of a major metro.
• Westerly: Retirees, families seeking a quiet upbringing, outdoor enthusiasts, and remote workers who want a scenic home base.

The Dollar Power: Where Does Your Money Work Harder?

This is where the rubber meets the road. At first glance, Westerly’s rent is slightly cheaper, but the real story is about purchasing power. Let’s break down the cold, hard numbers.

Cost of Living: A Tale of Two Budgets

Category	Chicago	Westerly CDP	The Verdict
Median Home Price	$365,000	$400,200	Westerly is surprisingly more expensive to buy.
Rent (1BR)	$1,507	$1,362	Westerly offers slightly cheaper rent.
Housing Index	110.7	98.9	Westerly is more affordable relative to its region.
Median Income	$74,474	$82,333	Westerly residents earn more on average.

The Salary Wars & Purchasing Power:
Let’s say you earn a solid $100,000. In Chicago, that’s about 34% above the median income, giving you a comfortable middle-class life. In Westerly, $100k is roughly 22% above the median, putting you in a similar relative position. However, the devil is in the details.

Chicago has an aggressive 9.5% combined city and state income tax (4.95% flat state + 2.5% city). On $100k, that’s $9,500 gone to income taxes before you even see your paycheck. Rhode Island, on the other hand, has a progressive state income tax topping out at 5.99%. On $100k, you’d pay roughly $5,990. That’s a difference of $3,510 annually—enough for a nice vacation or a hefty chunk of a mortgage payment.

But here’s the kicker: While Westerly has a lower tax bite, its median home price is higher. You’re earning more, paying less in taxes, but housing costs slightly more. It’s a wash in terms of pure dollars, but Chicago’s higher density offers more housing options at lower price points if you’re willing to look outside the trendy neighborhoods. The real "bang for your buck" in Chicago is in the rental market, where you can access a world-class city for a fraction of what a similar metro would charge.

The Housing Market: Buy vs. Rent, Availability & Competition

Chicago: The market is a complex beast. It’s a buyer’s market in many neighborhoods, especially outside the downtown core. You can find charming vintage apartments and single-family homes for under $300k in areas like Portage Park or Beverly. The competition is fierce for the "hot" areas (Lincoln Park, West Loop), but the city’s sheer size means inventory is constantly moving. Renting is a breeze for those not ready to commit, with endless high-rise and vintage options.

Westerly CDP: This is a seller’s market. As a coastal New England town, inventory is perpetually tight. The median home price of $400,200 reflects high demand from both locals and wealthy second-home buyers from NYC and Boston. Finding a home to buy is competitive and often requires patience. Renting is also challenging, as many properties are vacation rentals or long-term holds. The Housing Index of 98.9 is slightly below the national average, but in practice, it feels more expensive due to limited supply.

The Bottom Line: If you’re looking to buy a starter home without a bidding war, Chicago offers more opportunities. If you have a larger budget and are set on coastal living, Westerly is your target, but be prepared for a competitive search.

The Dealbreakers: Quality of Life, Weather, and Safety

This is where personal preference overrides data.

Traffic & Commute:

• Chicago: Infamous. The "L" is a lifesaver, but driving is a test of patience. Congestion is a daily reality. The average commute is 32 minutes. If you live and work in the city, public transit is your best friend.
• Westerly: Traffic is almost non-existent. A 10-minute drive can get you across town. The commute is a breeze, but you’re often dependent on a car for everything. The nearest major airport (T.F. Green) is about 45 minutes away.

Weather:

• Chicago: The data shows a winter low of 21°F, but the real enemy is the wind chill and the gray, relentless winters that can stretch from November to April. Summers are glorious and humid, hitting the 90°F mark. You need a serious winter wardrobe.
• Westerly: With a winter low of 46°F, it’s significantly milder than Chicago but still gets cold and snowy. However, it enjoys four distinct seasons with beautiful autumns and pleasant summers. The ocean moderates temperatures, but coastal storms (nor'easters) are a factor.

Crime & Safety:
This is the most critical dealbreaker. The data is stark.

• Chicago Violent Crime: 819.0 per 100k people. This is a real concern. While much of the city is safe, crime is highly neighborhood-dependent. You must do your research before choosing an area.
• Westerly Violent Crime: 159.5 per 100k people. This is dramatically lower, reflecting its status as a small, wealthy, and relatively isolated community. You can walk the streets at night with far less concern.

Verdict on Safety: If personal safety is your top priority, Westerly is the undeniable winner. Chicago requires vigilance and smart neighborhood selection.

The Final Verdict: Who Wins Each Category?

Let’s cut to the chase. Based on the data and lifestyle analysis, here’s how these two cities stack up for different life stages.

• Winner for Families: Westerly CDP

  • Why: The combination of extremely low violent crime (159.5/100k), top-rated public schools, a strong community, and access to nature makes it an ideal environment for raising children. The higher median income and slightly cheaper rent also help with the family budget.

• Winner for Singles & Young Professionals: Chicago

  • Why: The career opportunities are unparalleled. The cost of living, while high, is balanced by the tax burden and the sheer volume of rental options. The social scene, dating pool, and cultural amenities are what young professionals thrive on. It’s a city to hustle in.

• Winner for Retirees: Westerly CDP

  • Why: Safety is paramount in retirement. The slower pace, beautiful scenery, active (but not strenuous) outdoor lifestyle, and lower crime rate are perfect for a peaceful golden year. The mild climate, without Chicago’s brutal winters, is a huge plus.

Chicago: Pros & Cons

Pros:

• Unmatched Culture & Dining: From Michelin-starred restaurants to free summer festivals, you’ll never be bored.
• Job Market: A powerhouse in finance, tech, logistics, and healthcare.
• Public Transit: One of the best systems in the U.S., offering a car-free lifestyle.
• Housing Diversity: You can find almost any type of home at almost any price point.

Cons:

• High Crime Rate: Requires careful neighborhood research and awareness.
• Brutal Winters: The cold and gray skies are a major mood and health factor.
• Traffic & Congestion: Daily commutes can be draining.
• High Taxes: The combined income tax is a significant hit on your paycheck.

Westerly CDP: Pros & Cons

Pros:

• Extremely Low Crime: One of the safest communities in the region.
• Natural Beauty: Direct access to stunning beaches, parks, and coastal trails.
• Tight-Knit Community: Strong local identity and community events.
• Pleasant Weather: Milder winters than Chicago with beautiful seasonal changes.

Cons:

• Limited Job Market: Few major employers; reliant on tourism, service, and remote work.
• High Housing Demand: Competitive market with limited inventory.
• Isolation: Far from major metropolitan centers (2+ hours to Boston/NYC).
• Seasonal Economy: Can be quiet and closed in the off-season (winter).

The Bottom Line

Your choice boils down to a fundamental question: Do you want to live in a world of endless possibility, or a haven of peaceful simplicity?

If you’re in your 20s or 30s, building a career, and crave the energy of a city that never sleeps, Chicago is your battleground. You’ll pay in taxes and winter coats, but you’ll gain a lifetime of experiences and professional growth.

If you’re looking to raise a family in a safe environment, seeking a slower pace, or planning a retirement where your biggest worry is the tide, Westerly CDP is your sanctuary. You’ll trade job opportunities and urban buzz for clean air, quiet streets, and a lower stress level.

There’s no wrong answer, only the right fit for your next chapter. Choose wisely.