Chicago vs Winston-Salem for Veterans (2026)
Scroll down for VA loan estimates, military pension tax details, and FAQ.
Your move simulator
Tell us about your household — we calculate your real annual savings.
Estimated annual swing
−$9,621/yr
Favoring Winston-Salem for this income & household (illustrative).
With the extra $802/mo, you could pay down a $15,000 card balance in ~19 months and still keep ~$96/mo for dining out.
Complete the Picture
While you’re comparing — don’t leave money on the table.
Cash-back card
Best everyday cards for Winston-Salem
Maximize cash back on groceries, dining, and transit — categories that grow after a move.
High-yield savings
Park ~$9,621/yr savings at 4–5%+ APY
Even $802/mo extra earns meaningfully at 4–5% APY vs near-zero in checking.
Home + auto bundle
New state — compare rates before you sign
Moving to Winston-Salem resets your insurance profile. Bundling home + auto often saves 15–25%.
Veterans cost breakdown
| Metric | Chicago Illinois | Winston-Salem North Carolina | Your impact |
|---|---|---|---|
| 1BR rent / month | $1,900 | $1,300Better | $7,200/yr saves in Winston-Salem |
| Median home price | $360K | $260KBetter | — |
| State income tax on pension | 4.9% | 4.5%Better | $300/yr saves in Winston-Salem |
| Sales tax | 10.3% | 7%Better | — |
| Monthly utilities | $165 | $150Better | $180/yr saves in Winston-Salem |
| Military retire pay rent burden | 68% | 47%Better | — |
| Walk score | 78 / 100Better | 26 / 100 | — |
| Overall COL index | 107 | 87Better | — |
Your biggest money opportunities based on this comparison.
Pension tax savings
Winston-Salem saves ~$12/mo on military pension
No-tax states are a significant advantage on fixed military retirement income. Park the difference in a high-yield savings account.
VA home loan
Winston-Salem homes are $100K cheaper — $0 down with VA loan
VA loans require no down payment. Once you buy, protect your investment with homeowners insurance.
COL advantage
Winston-Salem stretches VA disability pay ~19% further
More purchasing power means more left to invest. Compare brokerage accounts and IRAs.
Complete the Picture
While you’re comparing — don’t leave money on the table.
Mortgages
See what you can afford in Winston-Salem
Compare rates from top lenders before your move — pre-approval is free and won't affect your score.
Home & Auto Insurance
Bundle before you move — save 15–25%
New state means new rates. Lock in Winston-Salem homeowners + auto quotes before your move date.
Moving Rewards Card
Turn closing costs & moving expenses into cash back
Average family spends $6,200 on a move. These cards pay 2–4% back + 0% intro APR on purchases.
Frequently asked questions
Which city is better for veterans — Chicago or Winston-Salem?
For veterans, Winston-Salem is the stronger choice based on tax burden on military pension, home affordability with VA loans, and walkability. Winston-Salem has the lower state tax rate on military pension income (4.5% vs 4.9%). Winston-Salem is more affordable overall, which matters when living on a fixed military retirement income.
Is military retirement pay taxed in Chicago and Winston-Salem?
As of 2026, Illinois taxes military retirement pay at 4.9%. North Carolina taxes military retirement pay at 4.5%. This is important because federal law does not tax VA disability compensation, but military pension IS subject to state income tax in most states. The difference on a $35K pension is roughly $12/month — or $144/year.
Can a veteran afford to buy a home in Chicago with a VA loan?
VA loans require no down payment, making homeownership more accessible for veterans. A VA loan on a $360K home in Chicago would run approximately $2,395/month at a 7% rate — that's 86% of the average military retirement take-home of $2,774/month. That's a stretch on military retirement pay alone — supplemental income or VA disability pay would help.
How far does VA disability pay go in Chicago vs Winston-Salem?
VA disability compensation is tax-exempt at the federal level, and most states also exempt it from state income tax. 100% P&T disability pay is approximately $3,737/month in 2026. In Winston-Salem (COL index 87), that $3,737 has the purchasing power of $4,295 in a 100-index (average US) city — effectively stretching further than in a higher-cost market.
Which city is more walkable and accessible for veterans with disabilities?
Chicago has a higher walk score (78 vs 26), meaning more daily errands, medical appointments, and services are accessible on foot or via transit. High walkability reduces car dependence — particularly valuable for veterans with mobility limitations or vision impairments. Walk scores above 70 are considered "very walkable."
A $35,000/year military pension in Chicago has the same purchasing power as $28K/year in Winston-Salem based on relative cost of living indexes.
Military retirement pay estimate based on 20-year E-7 equivalent (~$35,000/year). VA disability figures based on 2026 VA rating tables. State tax treatment of military pensions varies; verify your state's specific rules. Data: VA, Tax Foundation, Zillow, BLS · Q1 2026