✈️ Flight Guide: Houston (Any) → Key West (EYW)

May events in Key West can include food and music festivals, art walks, and maritime celebrations that elevate demand for flights and accommodations. Popular happenings often draw crowds for long weekends, so expect higher fares and limited hotel availability during festival dates. Plan ahead: book flights and lodging early, and consider arriving on weekday mornings to avoid peak transfer congestion. Check official event calendars for exact dates and ticket availability.

For May travel, midweek departures (Tuesday–Thursday) often yield lower fares and smaller crowds than weekend flights. Book 6–10 weeks in advance to capture favorable pricing, and avoid peak holiday weekends when demand spikes. Early morning flights can be less prone to weather delays and may be cheaper; late afternoon flights sometimes offer savings but can be affected by cascading delays. Monitor event dates in Key West, as festivals or concerts can drive up fares and hotel rates.

Nonstop flights are fastest and most convenient if available, typically saving 1–2 hours compared to one-stop itineraries. However, connecting flights via Miami (MIA) or Fort Lauderdale (FLL) often deliver lower fares and more schedule flexibility in May. If you prioritize time and minimal hassle, choose nonstop; if you prioritize price and departure time options, opt for a one-stop routing. For May trips, balance total door-to-door time and potential delays when selecting between direct and connecting flights.

Common carriers for Houston–Key West travel include American Airlines, Southwest (via networks), and Delta with connections. American often offers one-stop service through Miami with tight connections to EYW; Southwest may offer seasonal direct or connecting options with generous free checked bag policies. Delta typically connects via Atlanta or Miami with competitive pricing on some dates. Compare total price including baggage and seat selection when choosing an airline for May travel — a slightly higher base fare can be cheaper overall if baggage fees are lower.

May marks comfortable beach weather in Key West with warm waters good for snorkeling and boating. Pack reef-safe sunscreen, breathable fabrics, a light rain jacket, and a hat. Book snorkel trips, fishing charters, and accommodations in advance, especially around event weekends. Stay hydrated, protect electronics from humidity, and review local environmental rules for marine preserves. CTA: Prepare for May now — reserve activities and compare HOUA to EYW flight options to secure the best itinerary.

Nonstop flights, when available, typically take about 2 hours 45 minutes to 3 hours from the Houston area to Key West (EYW) depending on routing and winds. One-stop itineraries via Miami or Fort Lauderdale commonly add 1–3 hours of layover time, so total travel can range from 4.5 to 7 hours door-to-door. For May, airlines may add seasonal capacity on popular travel days; check real-time schedules and sign up for boarding alerts. When booking, allow at least 60–90 minutes for domestic connections in the same terminal, and 2+ hours if changing airports or terminals.

To secure cheap May flights from Houston (All Airports) (HOUA) to Key West (EYW), search 6–10 weeks out and use flexible date search tools to compare midweek vs weekend fares. Monitor fare alerts and consider one-stop routings through Miami (MIA) or Fort Lauderdale (FLL) if nonstop inventory is limited. Look for early morning or late evening departures, join airline newsletters for flash sales, and compare both Hobby (HOU) and IAH departure options to find the best deal. Booking rental cars and accommodations together in package deals can also reduce total trip cost.