Category / Metric	Redmond	Chicago
Financial Overview
Median Income	$172,979	$74,474
Unemployment Rate	4.6%	4.2%
Housing Market
Median Home Price	$1,350,000	$365,000
Price per SqFt	$625	$261
Monthly Rent (1BR)	$1,864	$1,507
Housing Cost Index	151.5	110.7
Cost of Living
Groceries Index	107.9	103.3
Gas Price (Gallon)	$3.65	$3.40
Safety & Lifestyle
Violent Crime (per 100k)	372.1	819.0
Bachelor's Degree+	76.4%	45.7%
Air Quality (AQI)	45	38

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

Welcome to the ultimate city showdown. You’re standing at a crossroads, and the path splits between two wildly different worlds. On one side, you have Chicago: the Windy City, a concrete jungle of deep-dish pizza, world-class museums, and a hustle that never sleeps. It’s a place where the subway rumbles under your feet and the skyline cuts a breathtaking silhouette against Lake Michigan.

On the other side, you have Redmond, Washington: the "Silicon Forest" hub, a serene, green-tech oasis nestled just outside Seattle. It’s home to Microsoft’s sprawling campus, lush parks, and a vibe that screams "work-life balance." Think evergreen trees, quiet neighborhoods, and a view of the Cascade Mountains instead of skyscrapers.

This isn't just a choice of geography; it's a choice of lifestyle. Are you chasing big-city energy or a peaceful, high-tech haven? Let's break it down, dollar by dollar, degree by degree, to help you find your perfect fit.

1. The Vibe Check: Culture & Lifestyle

Chicago is a city of neighborhoods, each with its own personality. From the historic brownstones of Lincoln Park to the vibrant arts scene in Wicker Park, there’s a pocket for every type of person. It’s a true 24/7 metropolis with a grit and authenticity you can’t fake. The culture is rich, diverse, and unapologetically Midwestern—friendly, but with a no-nonsense edge. It’s for the person who wants access to everything: pro sports, Broadway-caliber theater, a legendary food scene, and a nightlife that doesn’t quit. The lakefront is your backyard, and the city feels alive, pulsing with a creative and business energy that’s hard to match.

Redmond is the polar opposite. It’s a master-planned suburb that feels more like a well-oiled machine than a chaotic city. The vibe is calm, family-oriented, and deeply connected to nature. The city is dominated by tech workers who value their time off, leading to a culture centered around hiking, biking, and outdoor activities. It’s not about late-night clubs; it’s about weekend trips to the mountains or kayaking on Lake Sammamish. Redmond is for the person who craves quiet, safety, and a beautiful, predictable environment. It’s a haven for those who work hard in the tech field but want to decompress in a serene, green setting.

Verdict:

For the Urban Explorer: Chicago wins hands down.
For the Nature-Loving Professional: Redmond is your sanctuary.

2. The Dollar Power: Cost of Living & Salary

This is where the rubber meets the road. The salary numbers alone will shock you, but we need to dig into what that money actually buys.

Salary Wars: Purchasing Power

Let’s talk raw numbers. The median household income in Redmond is a staggering $172,979. In Chicago, it’s $74,474. That’s more than double. This is the "Microsoft effect"—high demand for tech talent drives wages sky-high.

But here’s the catch: Purchasing Power. Earning $172k sounds amazing, but if your rent is $2,000 and a house costs $1.35 million, your money doesn’t stretch as far. Conversely, earning $74k in a city where a median home is $365k and a 1BR apartment rents for $1,500 can feel surprisingly comfortable.

Bottom Line: You’ll earn more in Redmond, but you’ll also spend a lot more. In Chicago, your salary might be lower, but your daily expenses are significantly tamer.

The Cost of Living Breakdown

Category	Chicago (IL)	Redmond (WA)	Winner
Rent (1BR)	$1,507	$1,864	Chicago
Utilities (Basic)	~$160	~$180	Chicago
Groceries	~$330/month	~$380/month	Chicago
Median Home Price	$365,000	$1,350,000	Chicago
Housing Index	110.7	151.5	Chicago

Insight on Taxes: This is a huge swing. Washington has no state income tax. Illinois has a flat state income tax of 4.95%. If you earn $100k in Chicago, you’re paying ~$4,950 in state income tax. In Redmond, you keep that entire amount. This can offset some of the higher cost of living, especially for high earners.

Verdict for Your Wallet: If you’re moving with a high-salary tech job in hand, Redmond’s lack of state tax is a massive perk. If you’re on a more modest budget or don’t have a six-figure offer lined up, Chicago offers a far more affordable entry point into a major city.

3. The Housing Market: Buy or Rent?

The Renting Game

Both are competitive, but Redmond has a slight edge in price. For $1,507 in Chicago, you get a solid 1BR in a decent neighborhood. For $1,864 in Redmond, you’re in a newer, possibly tech-company-subsidized apartment complex. Availability is generally better in Chicago due to its sheer size, but Redmond’s market is tight due to the influx of tech workers.

The Buying Game

This is the biggest differentiator. In Chicago, the median home price is $365,000. You can find a condo or a single-family home in many neighborhoods. It’s a buyer’s market in many areas, with some price softening due to economic shifts and remote work.

In Redmond, the median home price is $1,350,000. This is not a typo. You’re looking at a seller’s market where bidding wars are common, and inventory is low. For the price of a median home in Redmond, you could buy a luxury property in Chicago’s most desirable neighborhoods. The barrier to entry in Redmond’s housing market is exceptionally high.

Verdict: For the average buyer, Chicago is vastly more accessible. Redmond is a market for high-income dual-earner households or those with significant equity from previous homes.

4. The Dealbreakers: Quality of Life

Traffic & Commute

Chicago has one of the most extensive public transit systems in the world (the "L"). You can live car-free in many neighborhoods. Traffic is brutal, but if you can commute by train, it’s manageable. Average commute time: 35 minutes.

Redmond is a car-centric suburb. Public transit exists but is limited. You will drive almost everywhere. The commute to Seattle can be a nightmare (I-405 is notoriously congested), but if you work at Microsoft’s campus, you might be able to bike or take a shuttle. Average commute time: 30 minutes (but highly variable).

Winner for Commute: Chicago (if you use transit).

Weather: The Big Chill vs. The Big Damp

Chicago is famous for its brutal winters. The data point of 21.0°F is a January average, but wind chills can easily plunge to -30°F. Summers are hot and humid (90°F+). It’s a city of extremes.

Redmond is mild. 48.0°F is a winter average. It’s rarely freezing. The trade-off is the "Big Damp"—months of gray, drizzly weather from October to April. Summers are glorious, dry, and in the 70s-80s.

Verdict: If you hate the cold, Redmond wins. If you hate gray skies and rain, Chicago might be better (you get four distinct seasons).

Crime & Safety

The data is stark. Chicago’s violent crime rate is 819.0 per 100k people. Redmond’s is 372.1 per 100k. Redmond is significantly safer. However, Chicago is a city of neighborhoods. Crime is highly concentrated. Areas like Lincoln Park or the Gold Coast are very safe, while others have higher rates. Redmond, as a suburb, has consistently low crime across the board.

Verdict for Safety: Redmond is objectively safer by the numbers.

5. The Final Verdict: Who Wins?

After weighing the data, the culture, and the costs, here’s the final breakdown.

👑 Winner for Families

Chicago

Why: While Redmond is safe and has great schools, the housing cost is a massive barrier for the average family. Chicago offers excellent public and private school options (in many neighborhoods), diverse cultural exposure for kids, and more affordable housing. The city’s parks, museums, and lakefront provide endless family activities.

👑 Winner for Singles & Young Professionals

Redmond (with a caveat)

Why: If you’ve landed a high-paying tech job, Redmond’s combination of high salary, no state tax, and easy access to Seattle’s social scene is unbeatable. The work-life balance is elite. However, if your salary is in the lower range or you crave a vibrant, diverse social scene outside the tech bubble, Chicago offers a richer, more affordable, and more stimulating environment for young singles.

👑 Winner for Retirees

Redmond

Why: For retirees with solid savings, Redmond is a dream. The mild climate (no shoveling snow!), low crime, beautiful scenery, and top-tier healthcare (Seattle is a medical hub) make it ideal. Chicago’s harsh winters and higher cost of living make it less appealing for fixed-income retirees, though its cultural amenities are a plus.

Final Pros & Cons List

🏙️ Chicago: The Gritty Metropolis

PROS:

Affordability: Significantly cheaper housing and cost of living.
Culture & Entertainment: World-class museums, theater, food, and sports.
Transit: Excellent public transportation, car-optional in many areas.
Diversity: A true melting pot of cultures, foods, and neighborhoods.
Lake Michigan: A stunning, free public resource for recreation.

CONS:

Weather: Brutal winters and humid summers.
Crime: High overall rates, though neighborhood-dependent.
Taxes: High property taxes and state income tax.
Traffic: Can be congested and stressful.

🌲 Redmond: The Serene Tech Haven