đź“Š Lifestyle Match
Visualizing the tradeoffs between Jackson and Chicago
Head-to-Head Analysis
Jackson vs Chicago
Detailed breakdown of cost of living, income potential, and lifestyle metrics.
đź“‹ The Details
Line-by-line data comparison.
| Category / Metric | Jackson | Chicago |
|---|---|---|
| Financial Overview | ||
| Median Income | $112,609 | $74,474 |
| Unemployment Rate | 3.4% | 4.2% |
| Housing Market | ||
| Median Home Price | $2,299,000 | $365,000 |
| Price per SqFt | $1170 | $261 |
| Monthly Rent (1BR) | $921 | $1,507 |
| Housing Cost Index | 111.5 | 110.7 |
| Cost of Living | ||
| Groceries Index | 95.1 | 103.3 |
| Gas Price (Gallon) | $3.40 | $3.40 |
| Safety & Lifestyle | ||
| Violent Crime (per 100k) | 234.2 | 819.0 |
| Bachelor's Degree+ | 55% | 45.7% |
| Air Quality (AQI) | 43 | 38 |
Expert Verdict
AI-generated analysis based on current data.
Chicago vs. Jackson: The Ultimate Head-to-Head Showdown
Choosing between two cities is rarely about spreadsheets—it’s about the life you want to build. In one corner, you have the Windy City: a sprawling, iconic metropolis where the skyline pierces the clouds and the energy is relentless. In the other, Jackson, Wyoming: a rugged, mountain-flanked town where the air is thin, the wilderness is your backyard, and the population is smaller than a single Chicago neighborhood.
This isn’t just a comparison of stats; it’s a clash of lifestyles. One is the ultimate urban grind, the other is the ultimate outdoor escape. Let’s break down where your dollar goes further, where you’ll feel safer, and which city is the right fit for your next chapter.
The Vibe Check: Urban Jungle vs. Mountain Hamlet
Chicago is the quintessential big city. It’s fast, loud, and endlessly complex. The culture here is a mosaic of world-class museums (the Art Institute, the Field Museum), a legendary food scene (deep-dish pizza, Michelin-starred spots, global cuisine in every neighborhood), and a sports obsession that fuels the city’s soul. The vibe is one of anonymity and opportunity—you can be anyone, and find your tribe. It’s for the ambitious professional who craves cultural depth, a bustling social scene, and the energy of millions within arm’s reach.
Jackson is a different beast entirely. Nestled in the Teton Range, it’s the gateway to Grand Teton and Yellowstone National Parks. The vibe is rugged, upscale outdoorsy. Think: "casual luxury" where a $200 fleece jacket is standard attire and the highlight of your week is a ski day or a trail run. The culture is built around nature, conservation, and a tight-knit community. It’s for the adventurer who values pristine air, breathtaking landscapes, and a slower, more intentional pace of life. The town is charming, but it’s small—you’ll run into the same people constantly.
Who is it for?
- Chicago is for the culture vulture, the foodie, the career climber, and anyone who needs the hum of a city to feel alive.
- Jackson is for the outdoor enthusiast, the retiree seeking serenity, and the remote worker who wants their office view to be the Tetons.
The Dollar Power: Where Does $100,000 Feel Like More?
At first glance, the numbers seem to flip expectations. You earn more in Jackson, but the cost of living tells a different story. Let’s talk purchasing power.
Salary Wars: The median income in Jackson is $112,609, nearly 50% higher than Chicago’s $74,474. This is largely because Jackson is a hub for high-income remote workers, wealthy retirees, and service-industry professionals catering to a tourist economy. However, this income buys a drastically different lifestyle.
The Cost of Living Table:
Note: Housing Index is a score where 100 is the national average. A score of 110 means 10% above average.
| Category | Chicago, IL | Jackson, WY | Winner (Affordability) |
|---|---|---|---|
| Median Income | $74,474 | $112,609 | Jackson |
| Median Home Price | $365,000 | $2,299,000 | Chicago (by a landslide) |
| Rent (1BR) | $1,507 | $921 | Jackson |
| Housing Index | 110.7 | 111.5 | Jackson (Slightly) |
| Violent Crime (per 100k) | 819.0 | 234.2 | Jackson |
Purchasing Power Insight:
Let's imagine you earn $100,000 in both cities. In Chicago, you’d be slightly above the median, and your $1,507 rent for a 1-bedroom is manageable. You could afford a decent lifestyle with plenty left over for dining, concerts, and public transit. The city’s high taxes (Illinois has a flat 4.95% state income tax) will take a bite, but the sheer volume of free and low-cost cultural events can offset it.
In Jackson, earning $100,000 puts you below the median income. Your $921 rent sounds like a steal, but it’s a mirage. That rent is likely for a small, older unit. The real cost is the $2.3 million median home price. To buy a "median" home, you’d need an income closer to $300,000. Furthermore, everything else—from groceries to gas to dining out—is inflated due to the remote, tourist-driven economy. You’ll have great access to the outdoors (often free), but your discretionary spending power will be significantly lower than in Chicago.
Verdict on Dollar Power: If you want your salary to stretch across a full life—housing, food, entertainment, and savings—Chicago offers far more bang for your buck. Jackson’s high income is necessary to survive its astronomical housing costs. For the average earner, Chicago’s lower barriers to entry make it the more financially sensible choice.
The Housing Market: Buy vs. Rent
Chicago: The Accessible Metropolis
- Buy vs. Rent: Renting is incredibly common in Chicago, with a robust market of high-rises, vintage walk-ups, and new luxury buildings. Buying is feasible for median-income earners, especially in neighborhoods beyond the Loop. The $365,000 median home price is within reach for dual-income professionals.
- Market Dynamics: Chicago is often a buyer’s market or balanced. Inventory is higher, and while prices have risen, they haven’t exploded to the same degree as coastal cities. You have negotiating power.
Jackson: The Exclusive Enclave
- Buy vs. Rent: The rental market is tight and competitive due to limited space and high demand from seasonal workers and tourists. Renting is your only realistic option unless you’re in the top 10% of earners.
- Market Dynamics: Jackson is a severe seller’s market. The median home price of $2,299,000 is staggering for a town of 10,746 people. This is driven by a lack of buildable land (protected by the Bridger-Teton National Forest and strict zoning), immense demand from wealthy second-home buyers, and a limited supply. You’re not just buying a house; you’re buying into an exclusive, scenic lifestyle. Expect bidding wars and cash offers well over asking.
Verdict on Housing: Chicago wins decisively for accessibility. It offers a path to homeownership for the middle class. Jackson’s housing market is a luxury good, accessible only to the wealthy.
The Dealbreakers: Quality of Life
This is where the cities diverge most dramatically.
Traffic & Commute:
- Chicago: Traffic can be brutal, ranked among the worst in the U.S. However, the public transit system (the 'L', Metra, buses) is one of the most extensive in the world. Many residents live car-free, a huge cost and stress saver. Commutes can still be long, but they are often productive on a train.
- Jackson: Traffic is minimal—except on summer weekends when tourist influx clogs the main roads. Most residents commute within town. The real commute is the 30-minute drive to the airport (Jackson Hole Airport, which is a stunning experience in itself). You will need a car, and it will be 4WD for the winters.
Weather:
- Chicago: Brutal winters. We’re talking sub-zero wind chills, heavy snow, and the famous "lake effect." Summers are glorious and humid, hitting 90°F+. It’s a city for people who can handle dramatic seasonal swings.
- Jackson: N/A°F for a reason—its weather is defined by elevation and mountains. Winters are cold and snowy, but dry and sunny. Summers are warm and dry, perfect for hiking. However, it’s high desert—expect big temperature swings between day and night. The air is dry, not humid.
Crime & Safety:
- Chicago: The data is sobering. With a violent crime rate of 819.0 per 100k, it’s significantly higher than the national average. Crime is highly concentrated in specific neighborhoods, but it affects the city’s overall perception and requires situational awareness.
- Jackson: The violent crime rate of 234.2 per 100k is much lower, closer to the national average. It’s generally considered safe, with petty crime (theft from cars, especially in trailheads) being the main concern. The small-town feel adds a layer of security.
Verdict on Quality of Life: This is a tie, depending on your priorities. Jackson wins on safety and weather (if you prefer dry winters). Chicago wins on transit and climate variety (if you crave four distinct seasons and hate driving).
The Verdict: Who Wins Your Relocation?
There is no single winner. The right city is the one that aligns with your non-negotiables. Let’s break it down by life stage.
| Winner For... | City | Why |
|---|---|---|
| Families | Chicago | While Jackson is safe, Chicago’s public schools (in good districts), world-class museums, zoos, and endless activities for kids provide an unparalleled urban upbringing. The cost of a single-family home is also more manageable. |
| Singles / Young Professionals | Chicago | The dating scene, networking opportunities, career growth, nightlife, and cultural events are unmatched. You can build a robust social and professional life without needing a car or a trust fund. |
| Retirees | Jackson | If you’re financially secure and prioritize peace, natural beauty, and an active outdoor lifestyle, Jackson is paradise. The safety and stunning scenery are ideal for a serene retirement. |
Final Pros & Cons
Chicago: Pros & Cons
đź‘Ť Pros:
- Unbeatable Culture: World-class museums, theaters, music, and food.
- Public Transit: One of the best systems in the U.S., making car ownership optional.
- Affordable Housing (Relatively): A median home price of $365,000 is attainable.
- Diverse Economy: Strong job market across finance, tech, healthcare, and more.
- Neighborhoods: 77 distinct neighborhoods, each with its own character.
đź‘Ž Cons:
- High Crime Rate: 819.0 violent crimes/100k requires caution and neighborhood research.
- Harsh Winters: Long, cold, and gray winters can be draining.
- Traffic & Commutes: Can be lengthy and stressful if you drive.
- High Taxes: Illinois has high property and state income taxes.
Jackson: Pros & Cons
đź‘Ť Pros:
- Stunning Natural Beauty: Gateway to Grand Teton & Yellowstone. Outdoor activities are unparalleled.
- Safety: Violent crime rate of 234.2/100k is significantly lower.
- Small-Town Community: Tight-knit, friendly, and easy to navigate.
- Clean Air & Environment: Pristine air quality and low pollution.
- Upscale Vibe: High-end amenities, restaurants, and boutiques.
đź‘Ž Cons:
- Astronomical Housing Costs: Median home price of $2,299,000 is prohibitive for most.
- Isolation: Far from major metros, limited shopping, and expensive flights.
- Tourist Overload: Summer and ski season bring massive crowds.
- Limited Job Market: Relies heavily on tourism and remote work.
- High Cost of Living: Everything from groceries to gas is expensive.
The Bottom Line: Choose Chicago if you want a vibrant, affordable, and dynamic urban life with world-class amenities at your doorstep. Choose Jackson if you have the means to afford a luxury mountain lifestyle and prioritize natural beauty and safety over urban excitement. For the vast majority of people, Chicago offers a more realistic and fulfilling path to building a life.