✈️ Flight Guide: Pittsburgh (PIT) → Key West (EYW)

May is a great month for Key West arrival activities such as Memorial Day weekend boating and beach events, the nightly Sunset Celebration at Mallory Square, and local restaurant weeks or food pop-ups that often occur in late spring. While major signature festivals frequently occur in other months, May offers increased opportunities for water sports, snorkeling charters, and smaller cultural events—making it ideal for travelers who prefer a more relaxed island vibe. If you plan to travel from Pittsburgh International Airport (PIT) around Memorial Day, book flights and accommodations early to avoid price spikes and limited inventory.

May is a very good time to fly from Pittsburgh International Airport (PIT) to Key West International Airport (EYW) if you want warm weather and fewer winter crowds. It's just before peak summer season and hurricane concerns become more pronounced, offering a sweet spot for sun and moderate prices. For the cheapest fares and smaller crowds, target midweek departures (Tuesdays and Wednesdays) and book about 6–10 weeks in advance. If your priority is the best weather, late February–May overall is ideal, with May offering warmer sea temperatures for snorkeling and boating.

Nonstop PIT→EYW flights are uncommon; most passengers travel via connecting flights through hubs like Miami (MIA), Charlotte (CLT), or Atlanta (ATL). Connecting flights often offer big savings and more schedule options, while direct flights (if available seasonally) reduce travel time but can be pricier. For May travel, balance layover length with the risk of delays—opt for 60–90 minute domestic connections in major hubs and use airline rebooking policies to protect tight itineraries. If your priority is minimizing travel time, choose the shortest total duration even if it costs slightly more; for budget travelers, a longer connection can yield lower fares.

American Airlines: Commonly routes PIT → MIA → EYW or PIT → CLT → EYW. Good connectivity and frequent schedules; consider Main Cabin vs. Basic Economy fares. Delta Air Lines: Often connects via ATL with reliable domestic network and SkyMiles benefits; fares may include varying baggage rules. United Airlines: Routes typically through Houston (IAH) or Newark (EWR) depending on schedule; MileagePlus perks and connections from PIT via partner hubs. JetBlue: Sometimes offers block-space or codeshare options through Boston or NYC then to Miami; known for legroom in standard coach and a pleasant in-flight experience if available on segments. For May, compare total travel time and baggage fees rather than base fare alone; loyalty status and credit-card benefits can meaningfully reduce out-of-pocket costs.

Pack lightweight clothing, reef-safe sunscreen, a light rain jacket, and water shoes for May travel to Key West. Because May marks the transition to wetter weather, confirm refundable or changeable flight options and consider travel insurance for last-minute weather disruptions. For departures from Pittsburgh International Airport (PIT), bring a reusable water bottle (fill after security), and enroll in TSA PreCheck to reduce wait times. Finally, reserve key activities—such as snorkeling tours or popular restaurants—ahead of arrival to secure the best times and rates.

There are typically no nonstop flights between Pittsburgh International Airport (PIT) and Key West International Airport (EYW); expect one-stop itineraries with total door-to-door times between 4.5 and 8+ hours, depending on connection length. Typical routing examples: PIT → MIA → EYW (total ~5–6 hours), PIT → CLT → EYW (total ~5.5–7 hours), or PIT → ATL → EYW (total ~6–8 hours). In May, airlines sometimes add seasonal frequencies or adjust schedules around Memorial Day weekend, so check current timetables and choose shorter layovers if you prefer minimal travel time. Use airline apps for real-time gate and delay updates and build a 60–90 minute minimum connection buffer for domestic-to-domestic transfers.

To find cheap flights from Pittsburgh International Airport (PIT) to Key West International Airport (EYW) in May, start searching 6–10 weeks before departure and use flexible dates to identify midweek savings. Sign up for email or app fare alerts and set price trackers for PIT→EYW to be notified of flash sales. Typical round-trip price ranges for May are approximately $250–$500; look for connecting itineraries through Miami (MIA) or Atlanta (ATL) for the lowest fares. Consider alternative nearby departure or arrival airports if your schedule is flexible: flying from Pittsburgh to Miami and then booking a separate short flight or ferry to the Keys can sometimes reduce cost. Use airline miles or credit card travel portals to lower out-of-pocket expenses and always compare baggage fees when evaluating low-cost itineraries.