Quick answer
Winston-Salem costs $850/month less overall ($1,545 vs $2,395/mo). Winston-Salem also has lower state income tax (4.75% vs 4.95%), widening the advantage for higher earners.
City Comparison · 2026
Chicago vs Winston-Salem
Side-by-side on rent, home prices, taxes, walkability, jobs, and climate — with a straight verdict for each type of mover.
Last updated: April 23, 2026
Chicago vs Winston-Salem at a Glance
| Metric | Chicago | Winston-Salem |
|---|---|---|
| 1BR Monthly Rent | $1,850 | $1,450 ✓ |
| 2BR Monthly Rent | $2,350 | $1,450 ✓ |
| Median Home Price | $340K ✓ | $385K |
| Avg Utilities/mo | $155 | $125 ✓ |
| Avg Groceries/mo | $390 | $320 ✓ |
| Monthly Cost (1BR) | $2,395 | $1,545 ✓ |
| Walk Score | 78/100 ✓ | 68/100 |
| Transit Score | 65/100 ✓ | 32/100 |
| State Income Tax | 4.95% | 4.75% ✓ |
Monthly cost = 1BR rent + utilities + groceries for one person. ✓ marks the lower/better value.
Cost of Living: What the Numbers Actually Mean
Rent gap: Winston-Salem's 1BR averages $1,100/month vs $1,850 in Chicago — a $750/month difference, or $9,000/year. That's a meaningful gap worth factoring into your decision.
State tax: Winston-Salem charges 4.75% state income tax vs 4.95% in Chicago. On an $80K salary that's a $160/year difference. On $120K, the gap grows to $5,940 vs $5,700 — important context if you're choosing between tech job offers.
Home buying: Median homes in Chicago are $340K vs $385K in Winston-Salem. At a 20% down payment, that's a $9,000 difference in upfront cash — significant at early-career savings rates.
Utilities: Chicago utilities run $30 more per month than Winston-Salem. Factor this into your all-in monthly budget.
Walkability, Transit & Daily Life
Chicago, IL
Chicago's walkability means you can genuinely live without a car in the right neighborhoods.
TOP NEIGHBORHOODS
Winston-Salem, NC
Winston-Salem's walkability means you can genuinely live without a car in the right neighborhoods.
TOP NEIGHBORHOODS
Climate
Chicago
Four true seasons; brutal winters (wind chills below -20°F common); outstanding summers
Winston-Salem
Four seasons: hot summers (85-92°F June-Aug), cold winters (35-45°F Dec-Feb) with occasional snow. Spring and fall are mild and pleasant.
Job Market
Chicago top industries
Winston-Salem top industries
Who Should Pick Which City
Move to Chicago if…
- →You're a urban explorers
- →You're a foodies
- →You're a architecture lovers
- →You're a transit users
- →You're a theater fans
- →You want to live without a car
- →You're buying a home and want more for your money
Move to Winston-Salem if…
- →You're a Remote workers wanting Southeast cost-of-living with real city infrastructure
- →You're a Healthcare and education professionals
- →You're a People wanting to buy a home affordably
- →You're a Anyone wanting four seasons, low taxes, and 40% cheaper cost-of-living than East Coast cities
- →You want to live without a car
Frequently Asked Questions
Is Chicago or Winston-Salem cheaper to live in?
Winston-Salem is cheaper overall. Monthly costs (1BR rent + utilities + groceries) run $1,545 in Winston-Salem vs $2,395 in Chicago — a $850/month difference.
Which city is more walkable — Chicago or Winston-Salem?
Chicago is more walkable with a Walk Score of 78/100 vs 68/100. Winston-Salem is more car-dependent.
Chicago vs Winston-Salem: which has lower state income tax?
Winston-Salem has lower state income tax (4.75%). On an $80K salary, that saves $160/year vs Chicago (4.95%).
Is Chicago or Winston-Salem better for buying a home?
Chicago has lower median home prices at $340K vs $385K in Winston-Salem — a $45,000 difference on the median home.