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Cheapest cached fares Chicago → Key West; typically 2 stops (e.g. F9). · Based on 3 fares found by travellers in the last 48h
Cheapest days highlighted · darker = pricier · past days greyed out · cached one-way fares.
Cheapest days highlighted · darker = pricier · past days greyed out · cached one-way fares.
Best value: Aug — fares from €131 and ~30°C daytime.
Flights from Chicago to Key West start around €131 (typically 2 stops). Range seen recently: €131–170, based on 3 fares found by travellers.
Fares found by travellers in the last 48 hours — refreshed daily.
In Aug, Key West typically sees ~30°C daytime highs and 16 rainy days.
3★+ hotels from €87/night (39 hotels sampled, ~3 weeks out).
Top-rated tours and tickets from €87 — book ahead for the popular ones.
Tours and tickets provided by Viator (a Tripadvisor company). Some links earn Stayonomy a commission.
Key West, in the Florida Keys, is a city and an island of the same name. It is the county seat of Monroe County and is considered the southernmost city in the continental United States.
Guide content from Wikivoyage contributors (CC BY-SA).
Cheapest destinations travellers searched recently — refreshed daily.
Flight prices are real fares travellers found in the last 48 hours, refreshed daily — the booking site confirms the final price. Train, bus and ferry fares are shown on the operators' booking sites. Weather data by Open-Meteo; exchange rates: ECB reference. Data updated 2026-08-02. Some links earn Stayonomy a commission at no cost to you.