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Winnipeg vs Chicago – Digital Nomad Guide

Trying to decide between Winnipeg, Canada and Chicago, United States? Here's a detailed comparison to help digital nomads and remote workers make an informed choice.

💰 Cost of Living

Winnipeg has a monthly cost of $3,900, which is 32.2% lower than Chicago's $5,750.

🌐 Internet Infrastructure

For internet speeds, Winnipeg offers 100 Mbps, while Chicago provides 100 Mbps making Chicago's connection 0.0% faster .

☀️ Current Weather

The weather in Winnipeg is currently 27°C 🌧️, while Chicago is experiencing 22°C 🌤️.

🛡️ Safety Comparison

Winnipeg has a safety score of 70.0 , while Chicago scores 55.0 .

Costs
$3,900
per month
Internet
100
Mbps
Weather
27° 🌧️
High today
Costs
$5,750
per month
Internet
100
Mbps
Weather
22° 🌤️
High today
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Revolut Ultra offers premium banking with global perks like lounge access, data, subscriptions, and insurance, ideal for frequent travelers.

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Overall

62.0
Overall Score
64.0

Quality of Life Winnipeg wins

70.0
Safety
55.0

Winnipeg is 15% better

85.0
Healthcare
79.0

Winnipeg is 6% better

Cost Winnipeg wins

61.0
Cost of Living
31.0

Winnipeg is 30% better

Climate Winnipeg wins

71.0
Air Quality
47.0

Winnipeg is 24% better

Infrastructure Chicago wins

78.0
Internet Speed
87.0

Chicago is 9% better

Social Chicago wins

59.0
Nightlife
80.0

Chicago is 21% better

72.0
Culture
86.0

Chicago is 14% better

69.0
Food Scene
87.0

Chicago is 18% better

Total Cost of Living Comparison

Category Winnipeg Chicago Difference
Monthly Total $3,900 $5,750 -32.2%
Daily Average $130 $192 per day

Housing

Item Winnipeg Chicago Difference
Apartment (1 bedroom) $850.00 per month $1,600.00 per month -46.9%

Daily Life

Item Winnipeg Chicago Difference
Coffee $3.50 per cup $3.50 per cup 0.0%

Transportation

Item Winnipeg Chicago Difference

Utilities

Item Winnipeg Chicago Difference
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Wise (formerly TransferWise) is a trusted money transfer service used by millions of digital nomads worldwide.

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Final Verdict: Winnipeg vs Chicago

Chicago ranks as the better digital nomad destination, scoring 2.0% higher than Winnipeg overall.

💰 Cost Analysis

  • Monthly Budget: $3,900 vs $5,750
  • Daily Expenses: $130 vs $192
  • Winnipeg 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

Winnipeg Wins In:
  • Safety (15% better)
  • Healthcare (6% better)
  • Cost of Living (30% better)
  • Air Quality (24% better)
Chicago Wins In:
  • Internet Speed (9% better)
  • Nightlife (21% better)
  • Culture (14% better)
  • Food Scene (18% better)

💡 Final Recommendation

Choose Chicago if you prioritize cost effectiveness and Internet Speed. However, Winnipeg might be preferable if Safety 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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Genki offers international health insurance tailored for digital nomads, expats, and long-term travelers, providing worldwide coverage and flexibility.

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