Category / Metric	Rutland	Chicago
Financial Overview
Median Income	$55,000	$74,474
Unemployment Rate	2.6%	4.2%
Housing Market
Median Home Price	$255,000	$365,000
Price per SqFt	$150	$261
Monthly Rent (1BR)	$997	$1,507
Housing Cost Index	123.6	110.7
Cost of Living
Groceries Index	105.3	103.3
Gas Price (Gallon)	$3.40	$3.40
Safety & Lifestyle
Violent Crime (per 100k)	173.3	819.0
Bachelor's Degree+	32.2%	45.7%
Air Quality (AQI)	34	38

Chicago vs. Rutland: The Ultimate Head-to-Head Showdown

So, you’re torn between the Windy City and a quiet Vermont town. This isn’t just a choice between two locations; it’s a choice between two entirely different universes. One is a high-octane, 24/7 global metropolis with deep-dish pizza and architectural marvels. The other is a quintessential New England gem, where the pace slows to a crawl and the air smells like pine and snow.

As your Relocation Expert, I’ve crunched the numbers and walked the vibes. This isn’t about which city is “better”—it’s about which city is better for you. Let’s dive in.

1. The Vibe Check: Big City Buzz vs. Small-Town Charm

Chicago
This is a city that never stops. Think of a sprawling, energy-packed playground where the skyline is your backdrop. The culture is a mosaic of world-class museums, a legendary food scene (from Michelin stars to iconic hot dogs), and a nightlife that hums until dawn. It’s a city for the go-getters, the networkers, and the culture vultures. You’ll find every ethnicity, cuisine, and subculture here. The vibe is ambitious, resilient, and unapologetically loud. It’s for the person who wants to be anonymous in a crowd but connected to the world.

Rutland, Vermont
Rutland is the definition of a "hidden gem." It’s a place where the community is tight-knit, and nature is your backyard. The vibe is laid-back, wholesome, and deeply connected to the outdoors. Think farmers' markets, craft breweries, and weekend hikes. It’s a town where you know your neighbors, shop local, and trade skyscrapers for mountain views. The pace is slower, the air is cleaner, and the stress is lower. It’s for the person seeking balance, tranquility, and a simpler, more grounded life.

Who It’s For:

Chicago: The ambitious professional, the foodie, the arts lover, the extrovert who thrives on social energy.
Rutland: The outdoors enthusiast, the remote worker seeking peace, the family prioritizing a safe, nature-filled upbringing, or the retiree wanting a quiet, scenic chapter.

2. The Dollar Power: Where Does Your Money Stretch Further?

Let’s be real: cost of living is often the ultimate deciding factor. But it’s not just about what you spend—it’s about what you get for it (purchasing power).

Cost of Living Snapshot Table

Category	Chicago	Rutland	Winner
Median Home Price	$365,000	$255,000	Rutland
Avg. Rent (1BR)	$1,507	$997	Rutland
Utilities (Monthly)	~$150	~$180	Chicago
Groceries	+12% above nat'l avg	+2% above nat'l avg	Rutland
Housing Index	110.7	123.6	Chicago

Salary Wars & Purchasing Power
Let’s play with a $100,000 salary. In Rutland, with a median home price of $255,000, that $100k goes incredibly far. You could comfortably afford a nice home, save aggressively, and enjoy a high quality of life without financial stress. The Housing Index of 123.6 is misleading—it’s high for Vermont, but compared to Chicago’s 110.7, it’s a different story. Rutland’s index is driven by limited inventory in a desirable state, not by mega-metro demand.

In Chicago, that same $100,000 feels different. After the $1,507 rent (or a $365,000 mortgage), plus higher taxes and city living expenses, your disposable income shrinks. However, Chicago’s median income of $74,474 is higher than Rutland’s $55,000, meaning higher earning potential exists here.

The Tax Verdict: Vermont has a progressive income tax (ranging from 3.35% to 8.75%). Illinois has a flat state income tax of 4.95%. For a $100k earner, you’ll pay less income tax in Illinois. However, Vermont’s property taxes are generally lower, and there’s no sales tax on clothing (a big deal for families). Chicago has a steep 10.25% sales tax. This is a complex equation, but for pure housing bang-for-your-buck, Rutland wins.

3. The Housing Market: Buy vs. Rent

Chicago
The market is competitive but vast. You can find anything from a studio condo in the Loop to a single-family home in the suburbs. Renting is the default for many newcomers. It’s a renter’s market with more options, but prices are high. Buying is a serious investment; the median home price of $365,000 is manageable for dual-income professionals, but property taxes in Cook County can be a shock. Availability is good, but desirable neighborhoods move fast.

Rutland
This is a classic seller’s market. The median home price of $255,000 is attractive, but inventory is brutally low. Vermont has a housing shortage, and Rutland is no exception. You’ll face bidding wars, especially for move-in-ready homes. Renting is also competitive, though cheaper ($997). If you’re looking to buy, you need to be patient, flexible, and ready to act fast. It’s a tough market for first-time buyers.

Verdict: For pure affordability, Rutland wins. For variety and ease of initial entry (renting), Chicago wins.

4. The Dealbreakers: Quality of Life

Traffic & Commute

Chicago: Brutal. The "El" is a lifesaver, but driving can be a nightmare. Commute times average 35-45 minutes. Parking is expensive and scarce.
Rutland: Non-existent. You can get across town in under 10 minutes. The biggest traffic jam is behind a tractor during harvest season.

Weather

Chicago: Famous for its brutal winters. We’re talking 21°F averages in January, biting winds, and lake-effect snow. Summers are hot and humid (90°F+). It’s a city for all four seasons, but winter is a serious commitment.
Rutland: A Vermont winter is also harsh (averaging 48°F in January, but that’s misleading; it’s regularly below freezing with heavy snow). The difference? Rutland is built for it. The community is prepared, and the winter wonderland is genuinely beautiful. Summers are milder and less humid.

Crime & Safety

This is a stark, data-driven reality check.

Chicago: The violent crime rate is 819.0 per 100,000. This is high—above the national average. It’s a city of neighborhoods, and safety varies drastically block by block. You must be street-smart.
Rutland: The violent crime rate is 173.3 per 100,000. This is significantly lower than Chicago and well below the national average. It’s one of the safest places in the Northeast.

Verdict: For safety and commute, Rutland is the clear winner. For weather, it’s a tie—it depends on your tolerance for snow vs. wind.

5. The Final Verdict: Which City Should You Choose?

After weighing the data and the lifestyle, here’s the breakdown.

Winner for Families

Rutland. The lower crime rate (173.3/100k vs 819.0/100k), more affordable housing ($255,000), and access to outdoor activities make it an ideal environment for raising kids. The school districts are solid, and the community is supportive.

Winner for Singles & Young Professionals

Chicago. The career opportunities are unparalleled. The social scene is vibrant, the networking potential is endless, and the cultural amenities are world-class. You’ll pay more, but you’ll live more.

Winner for Retirees

Rutland. The lower cost of living, peaceful environment, and stunning scenery offer a serene retirement. The slower pace and strong community are perfect for this life stage. Chicago’s hustle and high costs can be draining in later years.

Final Pros & Cons Lists

Chicago: Pros & Cons

Pros:

Unlimited Career & Cultural Opportunities: A global hub for business, arts, and food.
Public Transit: The ‘L’ system is extensive and reduces car dependency.
Diversity & Vibrancy: Every neighborhood offers a new world to explore.
Higher Median Income: $74,474 vs Rutland’s $55,000.

Cons:

High Cost of Living: Especially housing and taxes.
Violent Crime: Rates are a serious concern (819.0/100k).
Brutal Winters & Traffic: Can be mentally and physically taxing.
Competitive Housing Market: Buying is expensive.

Rutland: Pros & Cons