City comparison
Yes. Chicago's crime index is 167 versus 203 in Winston Salem, and its violent crime index is 139 versus 225, using 2024-2025 FBI data.
Winston Salem is cheaper. Median rent is $1,087 a month versus $1,440 in Chicago.
The income gap between Chicago and Winston Salem is significant: $77,902 median household versus $59,268. That spread matters more if you are job hunting locally than if you are remote. Typical rent is $1,440 in Chicago and $1,087 in Winston Salem.
Chicago is not a close call here. It leads on the job market, safety, and weather by margins that add up in daily life. Winston Salem makes sense if you have a specific reason, a job offer, family, or a neighborhood you already know, but on the numbers alone Chicago is the stronger move.
The rent gap is real but neighborhoods matter. Winston Salem at $1,087 average has pockets that run $887 and others at $1,487: your actual number depends on which part of the city you land in.
The move
Chicago and Winston Salem are 562 miles apart in a straight line.
Median rent goes from $1,440 a month in Chicago to $1,087 a month in Winston Salem, down $353 a month (25%).
Median household income goes from $77,902 in Chicago to $59,268 in Winston Salem, down $18,634 (24%).
The crime index goes from 167 in Chicago to 203 in Winston Salem, up 36 points (22%).
The move
Winston Salem and Chicago are 562 miles apart in a straight line.
Median rent goes from $1,087 a month in Winston Salem to $1,440 a month in Chicago, up $353 a month (32%).
Median household income goes from $59,268 in Winston Salem to $77,902 in Chicago, up $18,634 (31%).
The crime index goes from 203 in Winston Salem to 167 in Chicago, down 36 points (18%).
Chicago, IL
School quality varies by neighborhood. Check GreatSchools.org for current ratings.
Winston Salem, NC
School quality varies by neighborhood. Check GreatSchools.org for current ratings.
Comparing Chicago and Winston Salem? Check mortgage rates before you decide where to buy.
Rent
25% cheaper
Winston Salem rent is 25% cheaper than Chicago
Chicago
$1,440/mo
Winston Salem
Winner$1,087/mo
Typical rent runs $1,087 a month in Winston Salem versus $1,440 in Chicago, so Winston Salem is 25% cheaper. That's roughly $353/month back in your pocket ($4,236/year). Over five years that's $21,180 you could redirect toward a down payment, travel, or investments. Housing is the bill you pay before groceries, childcare, or a social life, so that gap shows up in how often you eat out and how panicked a rent hike feels. If you already have a high-paying offer in Chicago, the extra rent can be rational. If you do not, Winston Salem is the easier city to land in without blowing up your budget.
Planning to buy in Chicago? Check mortgage rates before you decide.
Median income
31% higher
Chicago's median income is 31% higher than Winston Salem
Chicago
Winner$77,902
Winston Salem
$59,268
Median household income is $77,902 in Chicago versus $59,268 in Winston Salem, so typical pay runs 31% higher in Chicago (about $18,634 more household income a year). Higher median income usually signals a stronger local job market and better negotiating leverage on salary. Remote workers should weigh this against cost of living rather than treating it as a direct personal benefit. For people who will actually work in town, Chicago is the stronger labor market on paper. Winston Salem can still win if housing is cheap enough to offset the weaker median or if your specific role already pays well there.
Crime index
18% lower crime
Chicago's crime index is 18% lower than Winston Salem
Chicago
Winner167 (100 = avg)
Winston Salem
203 (100 = avg)
Chicago's crime index is 167 versus 203 in Winston Salem (100 = national average), so citywide crime runs 18% lower in Chicago. That gap is meaningful day-to-day. It affects whether you feel comfortable walking at night, leaving your car on the street, or letting kids play outside unsupervised. Indexes still compress a lot of reality: a calmer city has blocks you would skip, and a higher-crime city has streets that feel neighborly at 10 p.m. On the everyday test of walking from the car to the door, Chicago is the easier city. Winston Salem can still work if you pick the right pocket. Just budget more diligence before you sign a lease.
Typical weather
4% more comfortable
Chicago weather is 4% more comfortable than Winston Salem
Chicago
Winner57°F avg · 64°F highs · comfort 78/100
Winston Salem
56°F avg · 66°F highs · comfort 75/100
Chicago averages about 57°F (64°F highs); Winston Salem averages about 56°F (66°F highs). Chicago averages around 57°F, so jackets, heating bills, and shorter outdoor seasons are part of daily life. Winston Salem averages around 56°F, so jackets, heating bills, and shorter outdoor seasons are part of daily life. Chicago scores 4% closer to the 65-80°F comfort band on this page, so it is the easier default for year-round outdoor errands and evenings. Choose Winston Salem if you already prefer its hotter or cooler pattern and have budgeted for the AC or heating that comes with it.
Fit check
Career-focused movers who want salary upside plus year-round outdoor access
It is also a match for career-focused movers who want salary upside and year-round outdoor access. Median household income runs 31% higher ($77,902), and typical weather is the more comfortable of the two (around 57°F). That pairing is for people who will work hard and then actually use the evenings.
Chicago is the better fit for families with young children and retirees who prioritize peace of mind over urban energy. The crime index is 18% lower than Winston Salem (167 vs a 100 national average). That gap shows up in how freely you walk at night and how much attention you spend on the car and the deadbolt.
Fit check
People with a job, family, or neighborhood already pulling them to Winston Salem
Winston Salem is the clearer landing pad if housing cost is what keeps you up at night. Typical rent is 25% cheaper here at about $1,087 a month. Choose Winston Salem if you are stretching a salary, starting over, or want slack for travel and debt instead of a flashier skyline.
Bottom line
Housing separates these metros first: $1,087/month in Winston Salem versus $1,440 in Chicago. Median income reads $59,268 in Winston Salem and $77,902 in Chicago, which matters when you stack rent against take-home pay.
Winston Salem rent at $1,087/month is still below Chicago's $1,440, so cost-sensitive households should weigh the lease before the paycheck.
Safety scores read 44/100 in Chicago and 38/100 in Winston Salem.
Pick Winston Salem when shaving $353 off rent at $1,087/month is the priority. Otherwise, Chicago's case rests on $1,440/month rent with $77,902 local income.
Common questions
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Next steps
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Nearby research
Open full neighborhood reports for Chicago and Winston Salem, plus other cities in IL and NC.
