Everything we know
35 categories for Chicago, grouped for quick scanning — coverage varies from city to city. Open any row for the full detail and any cited sources.
Money
Work
Life
Outdoor activities
Practical
The honest downsides
What we'd want to know before moving here.
Data last updated October 2026 · Verify anything important.
Other cities in North America
- New York, United StatesGlobal financial/cultural capital — standard tourist entry, not a nomad-visa destination.
- Jackson, United StatesGrand Teton's gateway — the Teton Crest Trail, storied alpine climbing, and an affluent remote-work-friendly mountain economy.
- Miami, United StatesMajor US gateway to Latin America, real nightlife/beach scene — standard tourist entry.
- Springdale, United StatesZion National Park's sole gateway town — Angels Landing, The Narrows, and a permit-based trekking scene in miniature.
- Hamilton, BermudaA small, upscale Atlantic hub with a dedicated remote-work visa, but an extremely high cost of living.
- Banff, CanadaIconic Canadian Rockies national-park town, real substantial ski access (Sunshine Village, Lake Louise, Mt. Norquay).
