Side-by-side city decision # Chicago vs Havana. A direct comparison of monthly costs, connectivity, safety, quality of life and remote-work fit. Share comparison Copy link ChicagoUnited States2/6 VS HavanaCuba2/6 $3,275Chicago monthly budget $1,335Havana monthly budget 260 MbpsChicago internet 15 MbpsHavana internet Decision summary No universal winner The result is balanced. Your priorities should decide the better fit. Cost Best budget Havana Speed Fastest internet Chicago Vibe Best nomad vibe Tie Safety Highest safety Havana Air Cleanest air Tie Walk Most walkable Chicago Quick read ## Two cities at a glance The headline numbers before you examine the full comparison. [Chicago](https://jobicy.com/cost-of-living/united-states/chicago.md) United States 2/6 Budget$3,275 Internet260 Mbps Vibe8/10 [Havana](https://jobicy.com/cost-of-living/cuba/havana.md) Cuba 2/6 Budget$1,335 Internet15 Mbps Vibe8/10 Full comparison ## Compare what matters Green marks the stronger numeric result. Text-only categories are presented without a winner. Differences only ### Monthly budget and costs 7 signals MetricChicagoHavana Total estimated budget $3,275 $1,335 1-bed center rent $2,200 $750 Coworking desk $450 $150 Local meal $22 $6.5 Cappuccino $5.5 $2.8 Gym membership $75 $35 Transport budget $75 $55 ### Work and infrastructure 2 signals MetricChicagoHavana Internet speed 260 Mbps 15 Mbps Nomad vibe 8/10 8/10 ### Quality of life 5 signals MetricChicagoHavana Safety index 48/100 63/100 Air quality 72/100 72/100 Walkability 8/10 7/10 Female safety 6/10 6/10 LGBTQ+ friendly 9/10 6/10 ### Culture and climate 4 signals MetricChicagoHavana Healthcare quality Excellent Average English proficiency Excellent Basic Climate type Humid continental Tropical savanna Best time to visit May - Oct Nov - Apr Beyond the numbers ## What each city asks you to trade Costs and scores help narrow the choice. These practical strengths and limitations finish the picture. [Chicago](https://jobicy.com/cost-of-living/united-states/chicago.md) United States → ### Strengths * Fast, reliable internet and extensive coworking options * Excellent public transit and highly walkable central neighborhoods * World-class food, music, museums, and architecture * Large international, startup, and remote-worker community * Strong healthcare and major airport connections * Inclusive LGBTQ+ scene and diverse neighborhoods ### Trade-offs * High rent, taxes, and everyday costs * Long, cold, windy winters * Safety varies sharply by neighborhood * Traffic and rush-hour trains can be crowded * US visitor status generally does not authorize local employment * Healthcare is expensive without suitable insurance ### Common visa routes * Visa Waiver Program / ESTA * B-2 visitor visa * H-1B or employer-sponsored work visa [Havana](https://jobicy.com/cost-of-living/cuba/havana.md) Cuba → ### Strengths * Exceptional music, architecture, and street life * Generally low violent-crime risk by regional standards * Walkable historic neighborhoods with strong character * Warm weather for most of the year * Affordable local transport and Cuban dining * Friendly and highly social local culture ### Trade-offs * Internet is slow, costly, and can be unreliable * Frequent shortages affect groceries, medicine, and household goods * International cards and online payments often do not work * No dedicated digital-nomad visa * Power interruptions can disrupt work routines * Housing quality and pricing vary sharply by access to foreign currency ### Common visa routes * Tourist Card / eVisa for eligible visitors * Family Visa for visitors with Cuban relatives * Business Visa through an approved Cuban host organization Reading the result ## Use this as a planning benchmark The headline score compares six directional signals. It does not weight personal priorities, visa eligibility, household size or individual lifestyle choices. Costs are monthly estimates, not guaranteed prices. Higher is better for quality scores and connectivity. Lower is better for budgets and individual expenses.