Cheapest places to fly from Islip 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 Islip: Boston (9K · 1h 27m) and Orlando (Southwest, JetBlue, Frontier). One stop via Baltimore: Cancun. No nonstop seen to Honolulu, Las Vegas, Los Angeles and New York on the dates searched recently.
Axel's pick: Boston, nonstop on 9K and the lowest fare saved for these dates, $377.
Where to fly from Islip 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.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips, entirely within May.
Cheapest right now: Boston $377 · Cancun $660 · Honolulu $965
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | Southwest Airlines | WN4506 + WN1609 | $235.00 | 2026-10-29T01:15:27Z |
| 2026-11-20 · one way | JetBlue Airways | B6513 + B62795 | $245.00 | 2026-10-29T01:15:27Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines | WN2238 + WN923 / WN1610 + WN1035 | $485.05 | 2026-10-29T01:15:27Z |
| 2026-11-20 → 2026-11-23 | JetBlue Airways | B6513 + B62795 / B61796 + B6514 | $495.95 | 2026-10-29T01:15:27Z |
| 2026-11-20 · one way | Southwest Airlines | WN2238 + WN923 | $235.00 | 2026-10-29T01:15:27Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines | WN4506 + WN1609 / WN1610 + WN1035 | $485.05 | 2026-10-29T01:15:27Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines | WN4506 + WN1609 / WN1610 + WN1035 | $485.05 | 2026-10-29T01:15:27Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines | WN2238 + WN923 / WN1610 + WN1035 | $485.05 | 2026-10-29T01:15:27Z |
| 2026-11-27 → 2026-12-04 | JetBlue Airways | B6513 + B62795 / B61796 + B6514 | $495.95 | 2026-10-29T01:15:27Z |
2026-11-20 · one way · $235.00
- Southwest Airlines WN4506 / WN1609: ISP 2026-11-20 06:05:00 → CUN 2026-11-20 13:10:00; 1 stop(s) via BWI; 425 minutes. Local airport times.
- WN4506: ISP 2026-11-20 06:05:00 → BWI 2026-11-20 07:25:00; layover at BWI: 120 minutes.
- WN1609: BWI 2026-11-20 09:25:00 → CUN 2026-11-20 13:10:00.
2026-11-20 · one way · $245.00
- JetBlue Airways B6513 / B62795: ISP 2026-11-20 06:00:00 → CUN 2026-11-20 14:00:00; 1 stop(s) via FLL; 480 minutes. Local airport times.
- B6513: ISP 2026-11-20 06:00:00 → FLL 2026-11-20 09:05:00; layover at FLL: 172 minutes.
- B62795: FLL 2026-11-20 11:57:00 → CUN 2026-11-20 14:00:00.
2026-11-27 → 2026-12-04 · $485.05
- Southwest Airlines WN2238 / WN923: ISP 2026-11-27 05:35:00 → CUN 2026-11-27 13:30:00; 1 stop(s) via MCO; 475 minutes. Local airport times.
- WN2238: ISP 2026-11-27 05:35:00 → MCO 2026-11-27 08:35:00; layover at MCO: 170 minutes.
- WN923: MCO 2026-11-27 11:25:00 → CUN 2026-11-27 13:30:00.
- Southwest Airlines WN1610 / WN1035: CUN 2026-12-04 16:25:00 → ISP 2026-12-04 23:45:00; 1 stop(s) via BWI; 440 minutes. Local airport times.
- WN1610: CUN 2026-12-04 16:25:00 → BWI 2026-12-04 19:45:00; layover at BWI: 165 minutes.
- WN1035: BWI 2026-12-04 22:30:00 → ISP 2026-12-04 23:45:00.
2026-11-20 → 2026-11-23 · $495.95
- JetBlue Airways B6513 / B62795: ISP 2026-11-20 06:00:00 → CUN 2026-11-20 14:00:00; 1 stop(s) via FLL; 480 minutes. Local airport times.
- B6513: ISP 2026-11-20 06:00:00 → FLL 2026-11-20 09:05:00; layover at FLL: 172 minutes.
- B62795: FLL 2026-11-20 11:57:00 → CUN 2026-11-20 14:00:00.
- JetBlue Airways B61796 / B6514: CUN 2026-11-23 15:05:00 → ISP 2026-11-23 22:04:00; 1 stop(s) via FLL; 419 minutes. Local airport times.
- B61796: CUN 2026-11-23 15:05:00 → FLL 2026-11-23 16:53:00; layover at FLL: 137 minutes.
- B6514: FLL 2026-11-23 19:10:00 → ISP 2026-11-23 22:04:00.
2026-11-20 · one way · $235.00
- Southwest Airlines WN2238 / WN923: ISP 2026-11-20 05:35:00 → CUN 2026-11-20 13:30:00; 1 stop(s) via MCO; 475 minutes. Local airport times.
- WN2238: ISP 2026-11-20 05:35:00 → MCO 2026-11-20 08:35:00; layover at MCO: 170 minutes.
- WN923: MCO 2026-11-20 11:25:00 → CUN 2026-11-20 13:30:00.
2026-11-27 → 2026-12-04 · $485.05
- Southwest Airlines WN4506 / WN1609: ISP 2026-11-27 06:05:00 → CUN 2026-11-27 13:10:00; 1 stop(s) via BWI; 425 minutes. Local airport times.
- WN4506: ISP 2026-11-27 06:05:00 → BWI 2026-11-27 07:25:00; layover at BWI: 120 minutes.
- WN1609: BWI 2026-11-27 09:25:00 → CUN 2026-11-27 13:10:00.
- Southwest Airlines WN1610 / WN1035: CUN 2026-12-04 16:25:00 → ISP 2026-12-04 23:45:00; 1 stop(s) via BWI; 440 minutes. Local airport times.
- WN1610: CUN 2026-12-04 16:25:00 → BWI 2026-12-04 19:45:00; layover at BWI: 165 minutes.
- WN1035: BWI 2026-12-04 22:30:00 → ISP 2026-12-04 23:45:00.
2026-11-20 → 2026-11-23 · $485.05
- Southwest Airlines WN4506 / WN1609: ISP 2026-11-20 06:05:00 → CUN 2026-11-20 13:10:00; 1 stop(s) via BWI; 425 minutes. Local airport times.
- WN4506: ISP 2026-11-20 06:05:00 → BWI 2026-11-20 07:25:00; layover at BWI: 120 minutes.
- WN1609: BWI 2026-11-20 09:25:00 → CUN 2026-11-20 13:10:00.
- Southwest Airlines WN1610 / WN1035: CUN 2026-11-23 16:25:00 → ISP 2026-11-23 23:45:00; 1 stop(s) via BWI; 440 minutes. Local airport times.
- WN1610: CUN 2026-11-23 16:25:00 → BWI 2026-11-23 19:45:00; layover at BWI: 165 minutes.
- WN1035: BWI 2026-11-23 22:30:00 → ISP 2026-11-23 23:45:00.
2026-11-20 → 2026-11-23 · $485.05
- Southwest Airlines WN2238 / WN923: ISP 2026-11-20 05:35:00 → CUN 2026-11-20 13:30:00; 1 stop(s) via MCO; 475 minutes. Local airport times.
- WN2238: ISP 2026-11-20 05:35:00 → MCO 2026-11-20 08:35:00; layover at MCO: 170 minutes.
- WN923: MCO 2026-11-20 11:25:00 → CUN 2026-11-20 13:30:00.
- Southwest Airlines WN1610 / WN1035: CUN 2026-11-23 16:25:00 → ISP 2026-11-23 23:45:00; 1 stop(s) via BWI; 440 minutes. Local airport times.
- WN1610: CUN 2026-11-23 16:25:00 → BWI 2026-11-23 19:45:00; layover at BWI: 165 minutes.
- WN1035: BWI 2026-11-23 22:30:00 → ISP 2026-11-23 23:45:00.
2026-11-27 → 2026-12-04 · $495.95
- JetBlue Airways B6513 / B62795: ISP 2026-11-27 06:00:00 → CUN 2026-11-27 14:00:00; 1 stop(s) via FLL; 480 minutes. Local airport times.
- B6513: ISP 2026-11-27 06:00:00 → FLL 2026-11-27 09:05:00; layover at FLL: 172 minutes.
- B62795: FLL 2026-11-27 11:57:00 → CUN 2026-11-27 14:00:00.
- JetBlue Airways B61796 / B6514: CUN 2026-12-04 15:05:00 → ISP 2026-12-04 22:04:00; 1 stop(s) via FLL; 419 minutes. Local airport times.
- B61796: CUN 2026-12-04 15:05:00 → FLL 2026-12-04 16:53:00; layover at FLL: 137 minutes.
- B6514: FLL 2026-12-04 19:10:00 → ISP 2026-12-04 22:04:00.
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- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Islip
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.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Boston (BOS) | Boston's Freedom Trail, universities and seafood | Nonstop · 9K · 1h 27m | $377 (airline $397) | May 8–15, 2027 | Check prices |
| Cancun (CUN) | Cancún's hotel zone, the Riviera Maya and Mayan ruins nearby | 1 stop via Baltimore | $660 (airline $696) | May 8–15, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki, Diamond Head and Pearl Harbor on Oahu | No nonstop seen | $965 (airline $1,020) | May 8–15, 2027 | Check prices |
| Las Vegas (LAS) | Las Vegas' Strip, shows and day trips to the canyons | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Orlando (MCO) | Orlando's theme parks | Nonstop · Southwest, JetBlue, Frontier | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Los Angeles (LAX) | Los Angeles' beaches, Hollywood and museums | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| New York (JFK) | New York's museums, Broadway and neighborhoods | No nonstop seen | No matching fare saved | May 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.
Keep exploring
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
Hotel details in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Express Hotel · Adhara Hacienda Cancun · All 172 hotels in Cancun
For AI assistants
- This page: Cheapest places to fly from Islip in May. Where to fly from Islip 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.