Head-to-Head Analysis

Hollywood vs Chicago

Detailed breakdown of cost of living, income potential, and lifestyle metrics.

Hollywood
Candidate A

Hollywood

FL
Cost Index 111.8
Median Income $61k
Rent (1BR) $1621
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Chicago
Candidate B

Chicago

IL
Cost Index 102.6
Median Income $74k
Rent (1BR) $1507
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📊 Lifestyle Match

Visualizing the tradeoffs between Hollywood and Chicago

đź“‹ The Details

Line-by-line data comparison.

Category / Metric Hollywood Chicago
Financial Overview
Median Income $60,630 $74,474
Unemployment Rate 4.2% 4.2%
Housing Market
Median Home Price $496,850 $365,000
Price per SqFt $363 $261
Monthly Rent (1BR) $1,621 $1,507
Housing Cost Index 156.4 110.7
Cost of Living
Groceries Index 102.9 103.3
Gas Price (Gallon) $2.60 $3.40
Safety & Lifestyle
Violent Crime (per 100k) 567.0 819.0
Bachelor's Degree+ 34.4% 45.7%
Air Quality (AQI) 33 38

Expert Verdict

AI-generated analysis based on current data.

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

You’re standing at a crossroads. On one side, you have the Windy City—a sprawling, gritty metropolis of deep-dish pizza, world-class architecture, and a culture that’s built on resilience. On the other, you have Hollywood—the glittering epicenter of dreams, where the sun shines almost every day and the red carpet is always rolled out.

It’s a classic clash of the titans: the Midwest powerhouse versus the West Coast icon. But this isn’t just about vibes; it’s about your wallet, your safety, and your sanity. As a relocation expert, I’ve crunched the numbers and felt the vibes so you don’t have to make this decision blind.

Let’s break it down.


1. The Vibe Check: Grit vs. Glamour

Chicago is the city that works. It’s a blue-collar heart with a white-collar brain. The vibe here is unpretentious, intellectual, and fiercely proud. You’ll find a dense, walkable downtown (The Loop) surrounded by distinct neighborhoods, each with its own personality. From the hipster haven of Logan Square to the upscale polish of Lincoln Park, Chicago offers a "big city" feel without the isolating anonymity of some coastal hubs. It’s a city for people who love food, theater, and sports, and who don’t mind trading a few gray winter days for a vibrant, affordable summer.

Hollywood, on the other hand, is pure fantasy. The vibe is laid-back, sun-drenched, and image-obsessed. It’s less a city and more a constellation of famous neighborhoods (Beverly Hills, West Hollywood, Los Feliz) within the vast Los Angeles metro. Life here revolves around the industry, the weather, and the outdoors. It’s for the dreamers, the hustlers, and the wellness gurus. The pace is slower, the sun is brighter, and the cost of living is a constant, nagging whisper in your ear.

Who is each city for?

  • Chicago is for the ambitious professional who wants a world-class city on a (relatively) reasonable budget, the foodie, the theater lover, and the family seeking top-tier public schools without breaking the bank.
  • Hollywood is for the creative (actor, writer, director), the outdoor enthusiast, the status-seeker, and the retiree who has already made their money and wants to spend their golden years in perfect weather.

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

Let’s talk real numbers. Earning $100,000 feels dramatically different in these two cities. First, the raw data on daily expenses.

Expense Category Chicago Hollywood Winner (Bang for Buck)
Median Home Price $365,000 $496,850 🏆 Chicago
Rent (1BR) $1,507 $1,621 🏆 Chicago
Utilities ~$180/month ~$160/month 🏆 Slight Edge: Hollywood
Groceries ~$350/month ~$380/month 🏆 Slight Edge: Chicago

Salary Wars & The Tax Hammer:
The data shows Hollywood has a ~10% higher median home price and rent. But the real kicker is taxes. California has a progressive income tax that can take up to 13.3% of your earnings, while Illinois has a flat rate of 4.95%.

Let’s do the math on that $100,000 salary:

  • Chicago: You keep roughly $95,050 after state tax.
  • Hollywood (LA County): You keep roughly $86,700 after state and local tax.

That’s an $8,350 difference—enough to cover a car payment, a vacation, or a hefty chunk of your rent. In Hollywood, you’re paying a "sunshine tax" and a "glamour tax." In Chicago, your purchasing power is significantly higher. You can afford a nicer apartment, save more, and still enjoy a night out.

Verdict: If you’re budget-conscious, Chicago gives you far more financial breathing room. Hollywood’s sticker shock is real, and the tax burden makes it even steeper.


3. The Housing Market: Buy vs. Rent

Buying in Chicago is one of the most accessible paths to homeownership in a major U.S. city. A median home price of $365,000 is a far cry from the million-dollar norms of coastal cities. The market is competitive, but it’s not a bloodbath. You can find single-family homes with yards in safe, family-friendly neighborhoods for under $400k. The market is stable, with a Housing Index (110.7) that suggests moderate demand.

Buying in Hollywood is a different beast. The median price of $496,850 is for the Hollywood area—a dense, urban part of LA. For a detached home in a desirable LA neighborhood, you’re often looking at $1M+. The Housing Index (156.4) screams "seller’s market." Inventory is chronically low, and bidding wars are common. It’s a game for those with deep pockets or who are willing to compromise on space and location.

Renting follows the same pattern. While Hollywood’s $1,621 for a 1BR isn’t astronomically higher than Chicago’s $1,507, the quality and space you get for that price in Hollywood are often far inferior. You’re paying a premium for the zip code and the weather.

Verdict: For buyers, Chicago is the undisputed winner. It’s a market where you can actually plant roots. For renters, Chicago still offers better value, but Hollywood’s rental market is brutally competitive.


4. The Dealbreakers: Quality of Life

Traffic & Commute:

  • Chicago: Traffic is bad, but it’s a commuter city. The public transit system (CTA) is extensive, cheap, and reliable. Many residents ditch their cars entirely, saving thousands on insurance, gas, and parking.
  • Hollywood: Los Angeles is the poster child for car dependency. Traffic is legendary, and public transit is improving but still sparse. You will spend a significant portion of your life in your car. The cost of car ownership is non-negotiable and adds $8,000-$12,000 annually to your budget.

Weather:

  • Chicago: Brutal winters. We’re talking 21°F averages in January, with lake-effect snow and biting winds. But the payoff is spectacular: gorgeous, vibrant springs and summers with festivals galore.
  • Hollywood: The data says 75°F, and it’s mostly true. Low humidity, endless sunshine. It’s idyllic for outdoor living year-round. However, the "May Gray" and "June Gloom" can bring overcast days, and the risk of wildfires and earthquakes is a real psychological factor.

Crime & Safety:

  • Chicago: The media loves to sensationalize Chicago’s crime. The data shows a violent crime rate of 819.0 per 100k. This is high, but it’s highly concentrated. The vast majority of the city’s neighborhoods are safe, especially on the North Side and in the suburbs. You must be savvy about where you live, but it’s not a warzone.
  • Hollywood: Violent crime is lower at 567.0 per 100k, but property crime is a significant issue. Car break-ins are rampant. The "Hollywood" area itself can be gritty, with a large homeless population and pockets of severe crime. Safety varies dramatically from block to block.

Verdict: Weather is a pure lifestyle choice. Safety is nuanced—Hollywood has lower violent crime, but both cities require urban awareness. Commute is a huge win for Chicago due to its transit system.


5. The Verdict: Who Should Pack Their Bags?

After weighing the data, the taxes, and the lifestyles, here’s the final showdown verdict.

🏆 Winner for Families: Chicago

Why: The math is undeniable. For the price of a small Hollywood condo, you can get a single-family home with a yard in a safe, top-rated school district in Chicago. The cultural amenities (museums, parks, libraries) are world-class and accessible. The lower tax burden means more money for college funds and family vacations. While the winters are tough, you get four distinct seasons and a strong sense of community.

🏆 Winner for Singles & Young Pros: Hollywood (with a caveat)

Why: If you’re in the entertainment, media, or creative industries, Hollywood is the epicenter. The networking opportunities, weather, and social scene are unparalleled. However, this win is only for those who have a clear career path that justifies the high cost. For everyone else—tech, finance, healthcare—Chicago offers a more balanced, affordable, and socially vibrant start to a career.

🏆 Winner for Retirees: Hollywood

Why: If you’ve already built your wealth and are looking to retire, Hollywood’s perfect weather and active lifestyle are hard to beat. The lower violent crime rate (though high property crime) and the focus on health and wellness are major draws. Chicago’s harsh winters can be physically challenging for seniors, making Hollywood a more comfortable choice for the golden years.


Final Pros & Cons Breakdown

Chicago: The Gritty Pragmatist

PROS:

  • Major Value: Highest purchasing power of any major U.S. city.
  • World-Class Culture: Second-to-none food, theater, architecture, and sports.
  • Excellent Transit: You can live car-free, saving thousands.
  • Accessible Housing: A realistic path to homeownership.
  • Vibrant Neighborhoods: A city of distinct communities.

CONS:

  • Brutal Winters: Long, cold, and gray from November to April.
  • High Taxes: A flat income tax and steep property taxes.
  • Concentrated Crime: Requires research and savvy neighborhood selection.
  • Harsh Winters: Not for those who hate the cold.

Hollywood: The Glamorous Dreamer

PROS:

  • Perfect Weather: Year-round sunshine and mild temps.
  • Outdoor Lifestyle: Hiking, beaches, and parks are always accessible.
  • Industry Hub: Unmatched opportunities in entertainment and creative fields.
  • Iconic Status: Living in a global symbol of fame and creativity.

CONS:

  • Extreme Cost: High rent, home prices, and the brutal "California Tax."
  • Car Dependency: Traffic is a daily grind; public transit is weak.
  • High Competition: Everything—from jobs to apartments—is a fierce battle.
  • Gritty Reality: The Hollywood dream has a harsh underbelly of inequality and homelessness.

The Bottom Line:
Choose Chicago if you want a big, affordable city with soul, seasons, and a path to stability. Choose Hollywood if you’re chasing a specific dream and are willing to pay a premium for perfect weather and iconic status. For most people, Chicago offers a more livable, sustainable, and financially smart life.