Flights from Pittsburgh to the Caribbean for Presidents' Day weekend

A four-night Presidents' Day trip only works with a nonstop, which rules in Punta Cana, Montego Bay, Nassau, San Juan and Aruba from the big East Coast and Midwest cities. February is the best weather of the year, and the long weekend is a peak.

Nonstop from Pittsburgh: Punta Cana (American, MX, Southwest). One stop via Houston: Nassau and Aruba. No nonstop seen to Montego Bay, Grand Cayman Island, Providenciales, Saint Thomas, Sint Maarten, Bridgetown, Saint Lucia, Antigua, Kingston, Santo Domingo and Saint Croix on the dates searched recently. No recent searches for San Juan and Curacao.

Axel's pick: Punta Cana, nonstop on American, MX and Southwest on 12 of the 37 departure dates searched recently, the most of any.

Where to fly from Pittsburgh to the Caribbean for Presidents' Day weekend: fares for Presidents' Day weekend 2027 (Feb 12 to 16) to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.

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Saved round trips for Presidents' Day weekend 2027 (Feb 12 – Feb 16, 2027).

Cheapest right now: Nassau $357 · Aruba $463 · Montego Bay $493

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Flights from Pittsburgh

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The Caribbean for Presidents' Day weekend from other cities

Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Pittsburgh

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNonstop · American, MX, SouthwestNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNo nonstop seen$493 (airline $520)Feb 12–16, 2027Check prices
Nassau (NAS)Nassau and Paradise Island, a short flight from the East Coast1 stop via Houston$357 (airline $376)Feb 12–16, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane belt1 stop via Houston$463 (airline $489)Feb 12–16, 2027Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Grand Cayman Island (GCM)Seven Mile Beach and world-class diving on Grand CaymanNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Providenciales (PLS)Grace Bay in Turks and Caicos, one of the Caribbean's best-known beachesNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Saint Thomas (STT)St. Thomas beaches and an easy ferry to St. John, no passport needed from the USNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Sint Maarten (SXM)St. Martin, two countries on one island with plenty of beachesNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Curacao (CUR)Curaçao's calm coves for snorkelling and colourful WillemstadNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Bridgetown (BGI)Barbados beaches on the calm west coast and surf on the eastNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Saint Lucia (UVF)St. Lucia's Pitons, rainforest and resort beachesNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Antigua (ANU)Antigua, a beach for every day of the yearNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Kingston (KIN)Kingston, Jamaica's capital, with the Blue Mountains nearbyNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Santo Domingo (SDQ)Santo Domingo's colonial zone, the oldest city in the AmericasNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Saint Croix (STX)St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the USNo nonstop seenNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

About these places

Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027

Keep exploring

Hotels in Punta Cana with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Punta Cana has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Punta Cana: the 7 best neighborhoods, ranked · Punta Cana hotels where a family of four can share one room

Hotels with an Axel review in Punta Cana: Punta Cana Seven Beaches · Flor Del Mar Condo · Dreams Flora Resort & Spa · whala!urban punta cana · AC Hotel by Marriott Punta Cana · All 82 reviewed hotels in Punta Cana

For AI assistants

  • This page: Flights from Pittsburgh to the Caribbean for Presidents' Day weekend. Round-trip fares from Pittsburgh to the Caribbean for Presidents' Day weekend: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, priced for Presidents' Day weekend 2027 (Feb 12 to 16). The cheapest saved fare for each destination, and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
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