1. Seattle, Washington
Seattle’s tech boom brought high salaries, but it also launched rent prices into the stratosphere. The average one-bedroom now goes for around $2,300, and competition is fierce for anything under that. Even tech-adjacent workers often share housing or commute from the suburbs. And side hustles? They’re part of the landscape—like coding bootcamp tutoring, photography, or managing Etsy stores.
The rain might keep you inside, but that just means more hours to work a second gig. Even in this coffee capital, barista wages don’t go far. Roommates are common, not just in your 20s, but deep into your 30s. The Emerald City still offers opportunities, but they come with a serious grind.
2. Los Angeles, California
Living in L.A. means paying premium prices for sunshine and proximity to your dreams—whether in acting, tech, or lifestyle branding. But with median rents pushing past $2,800 and gas prices consistently above the national average, the cost of living is no Hollywood fantasy. Many creatives share apartments deep into their 30s and keep multiple side gigs, from rideshare driving to social media consulting. That influencer posting matcha lattes might be your Lyft driver by night.
It’s not just struggling artists either—junior lawyers, nurses, and marketers are all living roommate-rich lives. The city sprawls, but affordable housing doesn’t. People budget down to the oat milk and live by the “Venmo me later” economy. It’s all about keeping up appearances on Instagram while quietly chasing rent money on TaskRabbit.
3. San Francisco, California
San Francisco has long been a tech mecca, but it’s also where a one-bedroom apartment can cost more than a used car—every single month. With median rents hovering around $3,000, most residents earning average wages are forced to split the bill. It’s not unusual for adults in their 30s and 40s to have multiple roommates just to stay within city limits. And that side hustle? Probably a necessity just to keep up with kombucha and Clipper Card refills.
Even tech workers aren’t immune—junior engineers at big-name firms often take on freelance gigs or DoorDash deliveries during off-hours. With sky-high costs and growing economic inequality, the city’s charm is now served with a side of burnout. It’s a beautiful place to live, but only if you can find someone to split that Victorian house with five ways. The American Dream here comes with roommates, ramen, and relentless rent apps.
4. New York, New York
In the city that never sleeps, it’s partly because rent is due and no one can afford to rest. Manhattan apartments can easily run over $4,000 a month, and Brooklyn isn’t far behind. That’s why even people with steady jobs often find themselves juggling roommates and late-night shifts—whether bartending, tutoring, or editing TikToks. The gig economy is alive and very necessary in NYC.
The city offers endless opportunity, but opportunity doesn’t always pay enough. One full-time job might cover groceries and a MetroCard, but not both rent and healthcare. Side hustles are baked into the lifestyle—photographers who also walk dogs, teachers who also sell vintage online. It’s glamorous from the outside, but it’s basically high-stakes musical chairs with rent-controlled apartments.
5. Boston, Massachusetts
Boston may be historic, but its housing market is anything but charming for your bank account. With rents averaging around $2,800 for a one-bedroom, splitting a place in Allston or Somerville is the norm, not the exception. Even those working in biotech, education, or healthcare often pair up with roommates to survive the steep costs. Meanwhile, side hustles abound—everything from tutoring SATs to making deliveries in the Back Bay.
The high density of universities and hospitals keeps job markets competitive, but also crowds the rental scene. Wages don’t always keep pace, especially for young professionals. It’s a city of smarts, but also of spreadsheet-level budgeting. The American Dream here wears Red Sox gear and lives with two roommates in a triple-decker.
6. Washington, D.C.
Living in the capital doesn’t come cheap, especially if you’re not on a government salary or corporate payroll. Average rents hover near $2,600 for a one-bedroom, and that’s if you can even find one in a decent neighborhood. Political aides, nonprofit workers, and junior lawyers often share houses—and not just for the camaraderie. Uber and food delivery gigs are common among the crowd juggling big dreams and small paychecks.
D.C. demands a high cost of living while offering inconsistent earning potential for newcomers. It’s a city of ambition, but also of spreadsheet budgeting. Side hustles like freelance writing or dog walking bridge the gap between rent and reality. You might be working toward changing the world, but first you have to Venmo your roommate for Wi-Fi.
7. Austin, Texas
Austin used to be affordable, but in the last few years it’s turned into Silicon Valley South. Median rents have jumped to over $1,800, and home prices have soared with tech migration. Locals and new arrivals alike are bunking up, often with strangers, just to hang onto the lifestyle. Uber driving, food delivery, and music gigs supplement paychecks that haven’t kept up.
It’s still weird, but now weird costs more. Creatives, coders, and bartenders alike share apartments while chasing side incomes. Everyone’s selling art, flipping vintage, or coding at night. In Austin, the dream still lives—but it probably has roommates and a part-time DJ setup.
8. Denver, Colorado
Denver has exploded in popularity, and so has its rent—up nearly 25% in just a few years. A one-bedroom apartment averages around $1,900, making shared housing nearly a default for those not pulling six figures. Millennials and Gen Zers here often juggle roommates, gigs, and the occasional cannabis shop job to make ends meet. It’s a laid-back city, but the hustle is real.
Side gigs are as common as snowboards. Locals moonlight as baristas, delivery drivers, or online sellers to cover everything from groceries to gear. The lifestyle is outdoorsy, but the economic reality is indoor spreadsheets. You might catch a sunrise hike, but only if you’re not working the night shift before it.
9. San Diego, California
San Diego is paradise with a premium. A typical one-bedroom costs around $2,500, and that’s not even beachfront. Even military personnel and healthcare workers often double up or split houses to stay close to work. Side hustles here include everything from surf lessons to food delivery.
The weather is perfect, but the financial strain is very real. People who want the lifestyle often settle for roommates and gig work to afford it. Teachers, office workers, and baristas alike are clocking second jobs just to stay afloat. The American Dream in San Diego now includes sunshine, surfing—and a third job.
10. Portland, Oregon
Portland’s rent has risen steeply in the past decade, now averaging around $1,800 for a one-bedroom. That’s pushed many artists, retail workers, and even junior tech employees into shared living situations. Side hustles are essential—selling handmade goods, freelance writing, or even ASMR YouTube channels. It’s creative, but also crowded and increasingly expensive.
The city prides itself on individuality, and people are getting inventive with income. The gig economy is thriving, partly by necessity. It’s all very Portland to share a craftsman home with four roommates and a rotating cast of cats. The dream still exists, but it has a communal kitchen and a shared Google Calendar.
11. Miami, Florida
Miami’s cost of living has spiked, especially with the post-pandemic influx of remote workers from pricier cities. The average rent is around $2,700, and service industry wages haven’t caught up. It’s not uncommon to find young professionals splitting luxury apartments to afford a slice of the Miami life. Meanwhile, rideshare driving and OnlyFans accounts quietly fund the beach days.
Glitz and grind coexist here in equal measure. Everyone wants the good life, but few can do it on just one income. The roommate lifestyle stretches well past college, and the hustle is as hot as the weather. Dreams may be big, but wallets are stretched tight under that South Beach sun.
12. Chicago, Illinois
Chicago isn’t the most expensive on the list, but with a median rent around $1,900 and stagnant wages in some sectors, shared living is still very common. Teachers, entry-level marketers, and artists often split walkups in Logan Square or Pilsen. The cost of groceries, transportation, and healthcare add up quickly. And yes, the side hustle is part of the Midwest grind now too.
Freelance design, part-time bartending, or weekend photography are common gigs supplementing full-time work. Chicago’s got character, but character doesn’t pay the bills. Even in the Heartland, roommates and hustle are how people stay afloat. The American Dream here comes with deep-dish and a full Google Sheets budget.
13. Philadelphia, Pennsylvania
Philly used to be the affordable East Coast secret, but prices have risen steeply in recent years. The average rent now hovers around $1,800, and wages haven’t caught up in many sectors. Sharing a rowhouse in Fishtown or West Philly is a go-to strategy. Many residents supplement income with tutoring, ride-share driving, or selling art online.
It’s a blue-collar city with big creative energy, but making it work often requires creative budgeting. You might meet a museum worker who also does pet sitting or a medical assistant who DJs on weekends. Side hustles aren’t just side interests—they’re financial lifelines. Philly is gritty and resilient, but no one’s paying rent here without backup.
14. Atlanta, Georgia
Atlanta’s boom has driven rents up, especially in trendy neighborhoods like Midtown or Old Fourth Ward. Average rent now exceeds $1,800, pricing many locals into roommate arrangements. Even full-time professionals often rely on side gigs like content creation, rideshare work, or reselling thrifted clothes. The city is entrepreneurial—but it has to be.
Tech and film industries have grown, but so have living expenses. It’s not unusual for someone with a corporate job to live like a college student just to save. The vibe is creative, but also chaotic. If you’re chasing dreams in Atlanta, you’d better bring a hustle and at least two roommates.
15. Nashville, Tennessee
Nashville’s housing prices have exploded alongside its popularity as a cultural hotspot. Rent averages around $1,900, and home prices are outpacing income. Music isn’t the only thing being played—many residents juggle day jobs, night gigs, and weekend side hustles. Roommates are just part of the local equation now.
You’ll find songwriters working at coffee shops and nurses delivering groceries after hours. It’s still a fun, vibrant place, but far from cheap. Dreams thrive here, but they definitely come with roommates, long hours, and side income. The American Dream might sing country, but it’s humming a tune of shared bills and extra gigs.
This post 15 Cities Where the American Dream Now Includes Three Roommates and a Side Hustle was first published on American Charm.
