Cheapest places to fly from Portland in May

May is the best-value month for Europe and the national parks: warm, long days, and fares a step below June. The beaches are quiet and cheap before summer, and Memorial Day weekend is the only peak.

Nonstop from Portland: San Diego (Alaska, Southwest), Austin (Alaska), Las Vegas (2h 10m), Puerto Vallarta (Alaska), Cancun (Alaska), Honolulu (6h 05m), San Jose Cabo (Alaska), Miami (American, Alaska), Los Angeles (Alaska, American, Delta) and San Francisco (Alaska, United), and 7 more. One stop via Dulles: Aruba. No nonstop seen to Punta Cana, Montego Bay, Nassau, San Juan and New Orleans on the dates searched recently. No recent searches for Orlando.

Axel's pick: San Diego, nonstop on Alaska and Southwest and the lowest fare saved for these dates, $349.

Where to fly from Portland in May: the cheapest saved round trips within May to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.

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Saved round trips, entirely within May.

Cheapest right now: San Diego $349 · Austin $350 · Las Vegas $394

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Flights from Portland

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Cheapest places in May from other cities

Fares observed October 21 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Portland

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
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · Alaska, Southwest$349 (airline $368)May 28–31, 2027Check prices
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · Alaska$350 (airline $370)May 8–15, 2027Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNonstop · 2h 10m$394 (airline $417)May 13–17, 2027Check prices
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNonstop · Alaska$653 (airline $690)May 26–31, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane belt1 stop via Dulles$745 (airline $786)May 8–15, 2027Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNonstop · Alaska$1,049 (airline $1,110) · 2 adultsMay 5–12, 2027Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on OahuNonstop · 6h 05m$3,047 (airline $3,219) · 3 adults · 2 childrenMay 11–18, 2027Check prices
Orlando (MCO)Orlando's theme parksNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of CortezNonstop · AlaskaNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNo nonstop seenNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNo nonstop seenNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNo nonstop seenNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo nonstop seenNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Miami (MIA)Miami's South Beach, Little Havana and art decoNonstop · American, AlaskaNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNonstop · Alaska, American, DeltaNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearbyNonstop · Alaska, UnitedNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · Alaska, DeltaNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · Alaska, JetBlueNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Chicago (ORD)Chicago's architecture, lakefront and deep-dishNonstop · Alaska, United, AmericanNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Denver (DEN)Denver's breweries and the Rockies within an hourNonstop · Alaska, United, SouthwestNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNonstop · Southwest, American, AlaskaNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNonstop · Delta, AlaskaNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · AlaskaNo matching fare savedMay 8 – May 15, 2027 (suggested)Search these dates
New Orleans (MSY)New Orleans' French Quarter, food and musicNo nonstop seenNo matching fare savedMay 8 – May 15, 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.

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Hotels in Cancun with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun 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 Cancun: the 8 best neighborhoods, ranked · Cancun hotels where a family of four can share one room

Hotels with an Axel review in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Hacienda Cancun · Akuazul Resorts Adults Only · All 148 reviewed hotels in Cancun

For AI assistants

  • This page: Cheapest places to fly from Portland in May. Where to fly from Portland in May: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within May, nonstop options first, 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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