Windsor vs Chicago – Digital Nomad Guide
Trying to decide between Windsor, Canada and Chicago, United States? Here's a detailed comparison to help digital nomads and remote workers make an informed choice.
💰 Cost of Living
Windsor has a monthly cost of $3,900, which is 32.2% lower than Chicago's $5,750.
🌐 Internet Infrastructure
For internet speeds, Windsor offers 100 Mbps, while Chicago provides 100 Mbps – making Chicago's connection 0.0% faster .
☀️ Current Weather
The weather in Windsor is currently 11°C 🌧️, while Chicago is experiencing 14°C 🌤️.
🛡️ Safety Comparison
Windsor has a safety score of 75.0 , while Chicago scores 53.0 .

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Overall
Chicago wins
Chicago is 6% better
Quality of Life
Windsor wins
Windsor is 22% better
Cost
Windsor wins
Windsor is 21% better
Climate
Windsor wins
Windsor is 14% better
Infrastructure
Chicago wins
Chicago is 11% better
Social
Chicago wins
Chicago is 33% better
Chicago is 26% better
Chicago is 30% better
Total Cost of Living Comparison
Category | Windsor | Chicago | Difference |
---|---|---|---|
Monthly Total | $3,900 | $5,750 | -32.2% |
Daily Average | $130 | $192 | per day |
Housing
Item | Windsor | Chicago | Difference |
---|---|---|---|
Apartment (1 bedroom) | $950.00 per month | $1,600.00 per month | -40.6% |
Daily Life
Item | Windsor | Chicago | Difference |
---|---|---|---|
Coffee | $3.50 per cup | $3.50 per cup | 0.0% |
Transportation
Item | Windsor | Chicago | Difference |
---|
Utilities
Item | Windsor | Chicago | Difference |
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Final Verdict: Windsor vs Chicago
Chicago ranks as the better digital nomad destination, scoring 6.0% higher than Windsor overall.
💰 Cost Analysis
- Monthly Budget: $3,900 vs $5,750
- Daily Expenses: $130 vs $192
- Windsor is 32.2% cheaper for digital nomads
🌐 Infrastructure
- Internet Speed: Chicago leads with 0% faster connection
- Public Transport: Chicago has better public transportation
🎯 Key Advantages
Windsor Wins In:
- Safety (22% better)
- Cost of Living (21% better)
- Air Quality (14% better)
Chicago Wins In:
- Overall Score (6% better)
- Internet Speed (11% better)
- Nightlife (33% better)
- Culture (26% better)
- Food Scene (30% better)
💡 Final Recommendation
Choose Chicago if you prioritize cost effectiveness and Overall Score. However, Windsor might be preferable if Overall Score is your top priority. Both cities offer unique advantages for digital nomads, with distinct trade-offs in cost of living, infrastructure, and lifestyle options.
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