$318 Economy Roundtrip to San Jose (BOS-SJO) in May from Boston

Logan International Airport (BOS) is a primary U.S. gateway for travelers flying to Juan Santamaría International Airport (SJO) in May. May marks the start of Costa Rica's green season, so travelers often hunt for lower fares and flexible fares from Boston while preparing for afternoon showers at the destination. Typical routing from Boston includes one-stop itineraries via Miami (MIA), New York (JFK/EWR), Atlanta (ATL) or Dallas (DFW); seasonal nonstop options may appear, so monitor schedules and set fare alerts. Plan for MBTA service, off-site parking reservations, and check terminal maps ahead of arrival. Nearby destinations like Cambridge, Providence, Cape Cod and Portland (ME) provide pre- or post-flight options for travelers combining New England sightseeing with a Costa Rica trip.

Departing from Boston (BOS) FAQs

In May, the fastest public option to Logan International Airport (BOS) from downtown Boston is the MBTA Blue Line + free Massport shuttle, which typically takes 20–30 minutes depending on your starting point. Rideshares and taxis are widely available but can be impacted by spring events and morning rush-hour traffic; allow extra time during May weekends and holiday weekends like Memorial Day. If you prefer driving, allow additional buffer for parking and security lines and consider booking airport parking in advance.

For an international flight from Logan International Airport (BOS) to Juan Santamaría International Airport (SJO) in May, arrive at least 2.5 to 3 hours before departure to allow time for check-in, security screening, and potential spring-season crowds. May is shoulder season for travel to Costa Rica, so you may encounter tourists and business travelers; check your airline's recommended arrival time and monitor TSA wait times on the Logan (BOS) website.

Logan International Airport (BOS) offers options including Hourly and Daily garages connected to terminals, the Economy Logan (shuttle-served), and off-site private long-term lots. For multi-day trips in May when rates and demand can vary, consider reserving an off-site lot with shuttle service or pre-booking the Economy lot to save money while keeping quick access to terminals. Compare prices and book ahead, especially during late-May holiday travel periods.

Nonstop service between Logan International Airport (BOS) and Juan Santamaría International Airport (SJO) can be seasonal. In May, you may find limited or seasonal nonstop options, but most itineraries will include one stop via hubs such as Miami (MIA), New York (JFK/EWR), Atlanta (ATL) or Dallas/Fort Worth (DFW). Check current airline schedules and book early if you specifically need a nonstop or single-connection flight.

For departures from Logan International Airport (BOS) to Juan Santamaría International Airport (SJO), pack liquids according to TSA 3-1-1 rules and verify your airline's checked-bag policy before travel; May is a good time to double-check weight limits due to potentially smaller aircraft on seasonal routes. Bring photocopies of passports, ensure required travel documents are valid for your stay in Costa Rica, and review any agricultural rules for returning with food or plants.

From Logan International Airport (BOS) you can easily access nearby major cities and top destinations such as Cambridge, Providence, New York City, Cape Cod, Portsmouth (NH) and Portland (ME) either before or after your international travel. Many travelers choose to combine a New England stay—like a Cape Cod beach visit or a Providence food tour—with flights out of BOS when flying to Juan Santamaría International Airport (SJO) in May.

Juan Santamaría International Airport (SJO) serves as the main international gateway for travelers flying from Logan International Airport (BOS) to Costa Rica in May. May signals the start of the green season—expect lush landscapes and afternoon showers—making it an ideal month for lower fares and vibrant nature tours. Upon arrival, follow immigration and customs signage, exchange a small amount of currency or use a bank ATM, and choose an authorized taxi, pre-booked shuttle, or rental car for onward travel to San José, Manuel Antonio, Jaco, Monteverde or Liberia (for Guanacaste). Consider private transfers for comfort during rainy conditions and double-check domestic flight schedules if connecting to beach or remote destinations.

Arriving at San Jose (SJO) FAQs

Arrivals at Juan Santamaría International Airport (SJO) in May typically encounter warm temperatures with increasing afternoon showers as the green season begins. Expect standard immigration and customs procedures, possible queues during peak arrival windows, and a range of ground transport options including official taxis, shuttles, and car rentals. Have local currency (Costa Rican colón) available for small purchases and be prepared for wet roads if you're heading to coastal or mountain destinations.

From Juan Santamaría International Airport (SJO) you can take an authorized taxi, shared shuttle, private transfer, or rental car to downtown San José; typical drive time is 20–30 minutes depending on traffic. In May, expect slightly slower drives during afternoon rains, so plan extra transit time for connections to other destinations like Manuel Antonio, Jaco, or Monteverde. Pre-booked airport shuttles and private transfers offer predictability during the busy green season.

As of May, standard entry requirements for most travelers include a valid passport with at least one blank page and a return or onward ticket; Costa Rica's entry rules can change, so verify requirements before travel. Routine health screening may be in place seasonally; ensure you check the Costa Rica Tourism Board and airline guidance for any vaccination or health advisories prior to departure.

From Juan Santamaría International Airport (SJO), travelers can reach popular destinations like Manuel Antonio, Jaco, Monteverde, Puntarenas, Liberia (LIR connections), and San José via private shuttle, shared transfer, domestic flights, or rental car. In May, road conditions can include wet surfaces and local traffic; consider private transfers for comfort and reliability or short domestic flights when available to reach Guanacaste or the Osa Peninsula faster.

Juan Santamaría International Airport (SJO) has currency exchange counters and ATMs in the arrivals area; however, exchange rates at the airport can be higher than in city banks. It's wise to withdraw a small amount of local currency (CRC) on arrival and use reputable exchange locations or withdraw from an ATM affiliated with major banks to reduce fees. Credit cards are widely accepted in tourist areas, but carry cash for markets and smaller operators.

After arriving at Juan Santamaría International Airport (SJO), top nearby destinations include downtown San José, Alajuela, Manuel Antonio, Jaco, Monteverde, Quepos, Puntarenas and the Guanacaste region (access via domestic flights or longer drives). May is a great month to explore cloud forests in Monteverde or coastal areas like Manuel Antonio with fewer crowds—just pack for periodic afternoon rain.

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Events & Festivals — Travel Considerations for BOS to SJO in May

May travel planning for Boston to Costa Rica should factor in local events and festivals. In the Boston area, May often features events such as the Boston Calling music festival (typically in May), Memorial Day observances, and spring cultural festivals in Cambridge and Providence. In Costa Rica, May marks the start of the green season; local celebrations include Mother’s Day (Día de la Madre) events in the second week of May and regional cultural fairs and eco-tours that celebrate the new rainy-season growth. These events can influence flight demand, local transportation, and availability of tours—book tours and transfers in advance.

Best Time to Fly from BOS to SJO — Why May is a Good Choice

The best time to fly from Logan International Airport (BOS) to Juan Santamaría International Airport (SJO) depends on priorities: for best beach weather and dry conditions, travel between December and April (high season); for lower fares and fewer crowds, May is an attractive shoulder-month with lush landscapes and more affordable rates. If you prefer minimal rain, schedule trips in late dry season (March–April); for lower prices and green-season scenery, choose May and aim for midweek departures to lower airfare.

Direct vs Connecting Flights — BOS to SJO in May

Choosing a direct (nonstop) flight vs a connecting itinerary from Logan International Airport (BOS) to Juan Santamaría International Airport (SJO) depends on priorities: nonstop saves time and reduces missed-connection risk but can be more expensive or seasonal; connecting flights often offer lower fares and more schedule flexibility. In May, nonstop options may be limited or seasonal, so many travelers opt for one-stop itineraries via Miami, New York, Atlanta or Dallas. If minimizing travel time is critical, seek nonstop or shortest-connection itineraries; if cost is the main driver, compare connections and use flexible dates to reduce fares.

Airline Comparison — BOS to SJO in May: JetBlue, American, Delta, United

Compare major carriers that typically serve routes between Boston (Logan International Airport (BOS)) and Costa Rica (arriving at Juan Santamaría International Airport (SJO)) in May. Airlines commonly used for this route include JetBlue (seasonal nonstop options on occasion), American Airlines (one-stop via Miami or Dallas), Delta Air Lines (one-stop via Atlanta or New York), and United Airlines (one-stop via Newark or Houston). Considerations: fare classes and baggage allowances vary, loyalty program benefits can affect upgrades, and in May many travelers prioritize price and connection time.

Seasonal Travel Tips for BOS to SJO in May — Packing, Health & Safety

Traveling in May from Logan International Airport (BOS) to Juan Santamaría International Airport (SJO) requires a mix of rain-ready packing and flexible planning. May ushers in Costa Rica's green season—expect lush landscapes, fewer crowds and afternoon showers. Pack quick-dry clothing, a waterproof layer, bug repellent, and sturdy shoes for rainforest trails. Bring a universal adapter, digital copies of important travel documents, and consider travel insurance that covers weather-related disruptions. For flights, choose morning departures to reduce the chance of weather-related delays affecting connections.

Flight Time & Schedules — Logan International Airport (BOS) to Juan Santamaría International Airport (SJO)

Average flight times between Logan International Airport (BOS) and Juan Santamaría International Airport (SJO) vary by routing. Nonstop flights (when available seasonally) typically take about 5 hours 45 minutes to 6 hours 30 minutes. Most itineraries in May include one connection, with total door-to-door times ranging from 7 to 12+ hours depending on the length and location of the layover. Key hubs for connections include Miami (MIA), New York (JFK/EWR), Atlanta (ATL) and Dallas/Fort Worth (DFW).

Cheap Flights from Logan International Airport (BOS) to Juan Santamaría International Airport (SJO) in May

Find cheap flights from Logan International Airport (BOS) to Juan Santamaría International Airport (SJO) in May by booking early, using flexible dates, and comparing carriers. Primary keywords to target searches include 'cheap flights BOS to SJO', 'Boston to San Jose Costa Rica deals', and 'May flights to SJO'. Secondary tactics: set fare alerts, search +/- 3 days around your target dates, consider nearby departure airports like T. F. Green/Providence (PVD) or Manchester (MHT) and compare one-stop itineraries via Miami (MIA), New York (JFK/EWR), Atlanta (ATL) or Dallas (DFW). Avoid weekend returns if possible; Tuesdays and Wednesdays often yield lower fares. Use LSI phrases such as 'low-cost Boston to Costa Rica flights', 'discount travel to San José in May', and 'budget flights BOS SJO'.

Tips

Book 6–12 weeks in advance for best May pricing; green season demand can lower prices but also add variability.
Set fare alerts with multiple providers and compare round-trip vs. two one-way fares.
Search alternate airports (PVD, MHT) and consider overnight layovers to unlock cheaper segments.
Travel midweek and use early-morning departures to capture lower-cost seats.

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