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15 Expensive Cities Where a Side Gig Is a Must



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A reality of modern life, especially life in large urban centers/big cities, is that median incomes often do not rise to the level of a city’s cost of living. In fact, in many large cities, the average cost of living is far higher than the median income — for example, the cost of living in Jackson, Wyoming, is nearly $100,000 higher than the median income. That’s deep, deep disparity.
Recently, GOBankingRates compiled the economic information for 600 large cities across America — taking such data as rent and mortgage levels, grocery prices, job statistics and more — to locate the cities that are so expensive you probably need a side gig to get by.
Side hustles aren’t for everyone; but, if you’re a resident of one of these 15 cities or are planning to move to one, note that a side hustle isn’t just suggested, it’s almost necessary.
See how much more money you need to earn above the median salary to live in these expensive cities — and side gigs that might help you do it.
Jackson, Wyoming
- Cost of living: $190,371
- Median income: $101,477
- Extra income needed: $88,894
- Top side gigs: Seasonal (winter) restaurant host/hostess, Instacart shopper
Edwards, Colorado
- Cost of living: $177,684
- Median income: $89,399
- Extra income needed: $88,285
- Top side gigs: Seasonal resort host (Edwards is very close to the resort city of Vail)
Steamboat Springs, Colorado
- Cost of living: $139,955
- Median income: $93,280
- Extra income needed: $46,675
- Top side gigs: Seasonal ski resort employee
San Luis Obispo, California
- Cost of living: $103,857
- Median income: $65,000
- Extra income needed: $38,857
- Top side gigs: California Polytechnic State University (CalPoly) tutor
Key West, Florida
- Cost of living: $115,780
- Median income: $80,828
- Extra income needed: $34,952
- Top side gigs: Seasonal boat tour guide, craft artisan (catering to the large tourist population)
Boulder, Colorado
- Cost of living: $105,769
- Median income: $80,243
- Extra income needed: $25,526
- Top side gigs: Outdoor guide (hiking, mountain biking), pet sitting, snow and sports instruction
Los Angeles
- Cost of living: $100,697
- Median income: $76,244
- Extra income needed: $24,453
- Top side gigs: Movie/TV extra, production assistant, ride-share driver, courier, dog-walking services
Ocean City, New Jersey
- Cost of living: $122,684
- Median income: $98,576
- Extra income needed: $24,108
- Top side gigs: Seasonal beach resort employee, tourism guide
Santa Cruz, California
- Cost of living: $124,889
- Median income: $105,491
- Extra income needed: $19,398
- Top side gigs: Farmers market delivery driver, Amazon Flex delivery driver
New York City
- Cost of living: $91,153
- Median income: $76,607
- Extra income needed: $14,546
- Top side gigs: Tutor, ride-share driver, dog walker, tour guide, bookkeeper
Kapaa, Hawaii
- Cost of living: $102,283
- Median income: $87,895
- Extra income needed: $14,388
- Top side gigs: Seasonal scuba instructor, rideshare driver during tourist season
Kahului, Hawaii
- Cost of living: $105,614
- Median income: $94,712
- Extra income needed: $10,902
- Top side gigs: Seasonal scuba trainer, seasonal tour guide
San Diego
- Cost of living: $107,787
- Median income: $98,657
- Extra income needed: $9,130
- Top side gigs: Barista, Taskrabbit, dog walker
Breckenridge, Colorado
- Cost of living: $136,304
- Median income: $129,481
- Extra income needed: $6,823
- Top side gigs: CDL delivery driver, seasonal parking attendant, winter season shuttle driver, ski technician
San Jose, California
- Cost of living: $137,721
- Median income: 136,010
- Extra income needed: $1,711
- Top side gigs: Summer nanny, wedding banquet bartender
Methodology: For this study, GOBankingRates analyzed cities across the United States for the best places you can buy a home for under $300,000. First GOBankingRates found cities where the average home value for single-family homes (November 2023 to November 2024) were under $300,000 and had no monthly value above $300,000. The 100 cities with the highest population were used for this study. For each city, GOBankingRates found total population, population ages 65 and over, total households, household median income, and the population below the poverty line, all sourced from the U.S. Census American Community Survey. The average single-family home values from November 2023 to November 2024 were sourced from Zillow Home Value Index. The cost of living was sourced from Sperling’s BestPlaces and includes the grocery, healthcare, housing, utilities, transportation and miscellaneous cost of living. Using the cost of living and the national average expenditure costs, as sourced from the Bureau of Labor Statistics Consumer Expenditure Survey, the average expenditure cost for each location was calculated. The livability index was sourced from AreaVibes for each location. Using the average home value, assuming a 10% down payment, and using the most recent national average 30-year fixed mortgage rate, as sourced from the Federal Reserve Economic Data, the average mortgage was calculated. Using the average mortgage and average expenditure costs, the average cost of living was calculated. All data is current through Dec. 30, 2024.
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