Cheapest places to fly from Hartford in May

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.

2026-11-20 · one way · $232.75

• Southwest Airlines WN445 / WN1609: BDL 2026-11-20 05:35:00 → CUN 2026-11-20 13:10:00; 1 stop(s) via BWI; 455 minutes. Local airport times.
  • WN445: BDL 2026-11-20 05:35:00 → BWI 2026-11-20 07:05:00; layover at BWI: 140 minutes.
  • WN1609: BWI 2026-11-20 09:25:00 → CUN 2026-11-20 13:10:00.

2026-11-20 · one way · $237.50

• JetBlue Airways B6959 / B61295: BDL 2026-11-20 07:50:00 → CUN 2026-11-20 16:15:00; 1 stop(s) via FLL; 505 minutes. Local airport times.
  • B6959: BDL 2026-11-20 07:50:00 → FLL 2026-11-20 11:09:00; layover at FLL: 184 minutes.
  • B61295: FLL 2026-11-20 14:13:00 → CUN 2026-11-20 16:15:00.

2026-11-20 · one way · $261.25

• United Airlines UA1764 / UA1677: BDL 2026-11-20 15:07:00 → CUN 2026-11-20 21:40:00; 1 stop(s) via IAD; 393 minutes. Local airport times.
  • UA1764: BDL 2026-11-20 15:07:00 → IAD 2026-11-20 16:30:00; layover at IAD: 77 minutes.
  • UA1677: IAD 2026-11-20 17:47:00 → CUN 2026-11-20 21:40:00.

2026-11-20 · one way · $270.75

• Delta Air Lines DL2233 / DL592: BDL 2026-11-20 08:00:00 → CUN 2026-11-20 15:07:00; 1 stop(s) via ATL; 427 minutes. Local airport times.
  • DL2233: BDL 2026-11-20 08:00:00 → ATL 2026-11-20 10:42:00; layover at ATL: 96 minutes.
  • DL592: ATL 2026-11-20 12:18:00 → CUN 2026-11-20 15:07:00.

2026-11-20 → 2026-11-23 · $465.03

• Southwest Airlines WN418 / WN386: BDL 2026-11-20 08:40:00 → CUN 2026-11-20 16:30:00; 1 stop(s) via BNA; 470 minutes. Local airport times.
  • WN418: BDL 2026-11-20 08:40:00 → BNA 2026-11-20 10:15:00; layover at BNA: 140 minutes.
  • WN386: BNA 2026-11-20 12:35:00 → CUN 2026-11-20 16:30:00.
• Southwest Airlines WN904 / WN2866: CUN 2026-11-23 13:40:00 → BDL 2026-11-23 21:05:00; 1 stop(s) via MCO; 445 minutes. Local airport times.
  • WN904: CUN 2026-11-23 13:40:00 → MCO 2026-11-23 15:45:00; layover at MCO: 150 minutes.
  • WN2866: MCO 2026-11-23 18:15:00 → BDL 2026-11-23 21:05:00.

2026-11-20 → 2026-11-23 · $470.25

• JetBlue Airways B6959 / B61295: BDL 2026-11-20 07:50:00 → CUN 2026-11-20 16:15:00; 1 stop(s) via FLL; 505 minutes. Local airport times.
  • B6959: BDL 2026-11-20 07:50:00 → FLL 2026-11-20 11:09:00; layover at FLL: 184 minutes.
  • B61295: FLL 2026-11-20 14:13:00 → CUN 2026-11-20 16:15:00.
• JetBlue Airways B61296 / B6460: CUN 2026-11-23 16:55:00 → BDL 2026-11-23 23:59:00; 1 stop(s) via FLL; 424 minutes. Local airport times.
  • B61296: CUN 2026-11-23 16:55:00 → FLL 2026-11-23 18:45:00; layover at FLL: 129 minutes.
  • B6460: FLL 2026-11-23 20:54:00 → BDL 2026-11-23 23:59:00.

2026-11-20 → 2026-11-23 · $512.05

• United Airlines UA1764 / UA1677: BDL 2026-11-20 15:07:00 → CUN 2026-11-20 21:40:00; 1 stop(s) via IAD; 393 minutes. Local airport times.
  • UA1764: BDL 2026-11-20 15:07:00 → IAD 2026-11-20 16:30:00; layover at IAD: 77 minutes.
  • UA1677: IAD 2026-11-20 17:47:00 → CUN 2026-11-20 21:40:00.
• United Airlines UA1133 / UA274: CUN 2026-11-23 16:55:00 → BDL 2026-11-23 23:59:00; 1 stop(s) via IAD; 424 minutes. Local airport times.
  • UA1133: CUN 2026-11-23 16:55:00 → IAD 2026-11-23 20:19:00; layover at IAD: 132 minutes.
  • UA274: IAD 2026-11-23 22:31:00 → BDL 2026-11-23 23:59:00.

2026-11-20 → 2026-11-23 · $521.55

• Delta Air Lines DL2233 / DL592: BDL 2026-11-20 08:00:00 → CUN 2026-11-20 15:07:00; 1 stop(s) via ATL; 427 minutes. Local airport times.
  • DL2233: BDL 2026-11-20 08:00:00 → ATL 2026-11-20 10:42:00; layover at ATL: 96 minutes.
  • DL592: ATL 2026-11-20 12:18:00 → CUN 2026-11-20 15:07:00.
• United Airlines UA1133 / UA274: CUN 2026-11-23 16:55:00 → BDL 2026-11-23 23:59:00; 1 stop(s) via IAD; 424 minutes. Local airport times.
  • UA1133: CUN 2026-11-23 16:55:00 → IAD 2026-11-23 20:19:00; layover at IAD: 132 minutes.
  • UA274: IAD 2026-11-23 22:31:00 → BDL 2026-11-23 23:59:00.

2026-11-27 → 2026-12-04 · $476.15

• Southwest Airlines WN455 / WN218: BDL 2026-11-27 12:55:00 → CUN 2026-11-27 20:25:00; 1 stop(s) via MDW; 450 minutes. Local airport times.
  • WN455: BDL 2026-11-27 12:55:00 → MDW 2026-11-27 14:25:00; layover at MDW: 80 minutes.
  • WN218: MDW 2026-11-27 15:45:00 → CUN 2026-11-27 20:25:00.
• Southwest Airlines WN904 / WN2866: CUN 2026-12-04 13:40:00 → BDL 2026-12-04 21:05:00; 1 stop(s) via MCO; 445 minutes. Local airport times.
  • WN904: CUN 2026-12-04 13:40:00 → MCO 2026-12-04 15:45:00; layover at MCO: 150 minutes.
  • WN2866: MCO 2026-12-04 18:15:00 → BDL 2026-12-04 21:05:00.

2026-11-20 · one way · $232.75

• Southwest Airlines WN418 / WN386: BDL 2026-11-20 08:40:00 → CUN 2026-11-20 16:30:00; 1 stop(s) via BNA; 470 minutes. Local airport times.
  • WN418: BDL 2026-11-20 08:40:00 → BNA 2026-11-20 10:15:00; layover at BNA: 140 minutes.
  • WN386: BNA 2026-11-20 12:35:00 → CUN 2026-11-20 16:30:00.

2026-11-20 · one way · $232.75

• Southwest Airlines WN455 / WN218: BDL 2026-11-20 12:55:00 → CUN 2026-11-20 20:25:00; 1 stop(s) via MDW; 450 minutes. Local airport times.
  • WN455: BDL 2026-11-20 12:55:00 → MDW 2026-11-20 14:25:00; layover at MDW: 80 minutes.
  • WN218: MDW 2026-11-20 15:45:00 → CUN 2026-11-20 20:25:00.

2026-11-20 → 2026-11-23 · $465.03

• Southwest Airlines WN455 / WN218: BDL 2026-11-20 12:55:00 → CUN 2026-11-20 20:25:00; 1 stop(s) via MDW; 450 minutes. Local airport times.
  • WN455: BDL 2026-11-20 12:55:00 → MDW 2026-11-20 14:25:00; layover at MDW: 80 minutes.
  • WN218: MDW 2026-11-20 15:45:00 → CUN 2026-11-20 20:25:00.
• Southwest Airlines WN904 / WN2866: CUN 2026-11-23 13:40:00 → BDL 2026-11-23 21:05:00; 1 stop(s) via MCO; 445 minutes. Local airport times.
  • WN904: CUN 2026-11-23 13:40:00 → MCO 2026-11-23 15:45:00; layover at MCO: 150 minutes.
  • WN2866: MCO 2026-11-23 18:15:00 → BDL 2026-11-23 21:05:00.

2026-11-20 → 2026-11-23 · $465.03

• Southwest Airlines WN445 / WN1609: BDL 2026-11-20 05:35:00 → CUN 2026-11-20 13:10:00; 1 stop(s) via BWI; 455 minutes. Local airport times.
  • WN445: BDL 2026-11-20 05:35:00 → BWI 2026-11-20 07:05:00; layover at BWI: 140 minutes.
  • WN1609: BWI 2026-11-20 09:25:00 → CUN 2026-11-20 13:10:00.
• Southwest Airlines WN904 / WN2866: CUN 2026-11-23 13:40:00 → BDL 2026-11-23 21:05:00; 1 stop(s) via MCO; 445 minutes. Local airport times.
  • WN904: CUN 2026-11-23 13:40:00 → MCO 2026-11-23 15:45:00; layover at MCO: 150 minutes.
  • WN2866: MCO 2026-11-23 18:15:00 → BDL 2026-11-23 21:05:00.

2026-11-27 → 2026-12-04 · $476.15

• Southwest Airlines WN418 / WN386: BDL 2026-11-27 08:40:00 → CUN 2026-11-27 16:30:00; 1 stop(s) via BNA; 470 minutes. Local airport times.
  • WN418: BDL 2026-11-27 08:40:00 → BNA 2026-11-27 10:15:00; layover at BNA: 140 minutes.
  • WN386: BNA 2026-11-27 12:35:00 → CUN 2026-11-27 16:30:00.
• Southwest Airlines WN904 / WN2866: CUN 2026-12-04 13:40:00 → BDL 2026-12-04 21:05:00; 1 stop(s) via MCO; 445 minutes. Local airport times.
  • WN904: CUN 2026-12-04 13:40:00 → MCO 2026-12-04 15:45:00; layover at MCO: 150 minutes.
  • WN2866: MCO 2026-12-04 18:15:00 → BDL 2026-12-04 21:05:00.

2026-11-27 → 2026-12-04 · $476.15

• Southwest Airlines WN445 / WN1609: BDL 2026-11-27 05:35:00 → CUN 2026-11-27 13:10:00; 1 stop(s) via BWI; 455 minutes. Local airport times.
  • WN445: BDL 2026-11-27 05:35:00 → BWI 2026-11-27 07:05:00; layover at BWI: 140 minutes.
  • WN1609: BWI 2026-11-27 09:25:00 → CUN 2026-11-27 13:10:00.
• Southwest Airlines WN904 / WN2866: CUN 2026-12-04 13:40:00 → BDL 2026-12-04 21:05:00; 1 stop(s) via MCO; 445 minutes. Local airport times.
  • WN904: CUN 2026-12-04 13:40:00 → MCO 2026-12-04 15:45:00; layover at MCO: 150 minutes.
  • WN2866: MCO 2026-12-04 18:15:00 → BDL 2026-12-04 21:05:00.

2026-11-27 → 2026-12-04 · $481.50

• JetBlue Airways B6959 / B61295: BDL 2026-11-27 07:50:00 → CUN 2026-11-27 16:15:00; 1 stop(s) via FLL; 505 minutes. Local airport times.
  • B6959: BDL 2026-11-27 07:50:00 → FLL 2026-11-27 11:09:00; layover at FLL: 184 minutes.
  • B61295: FLL 2026-11-27 14:13:00 → CUN 2026-11-27 16:15:00.
• JetBlue Airways B61296 / B6460: CUN 2026-12-04 16:55:00 → BDL 2026-12-04 23:59:00; 1 stop(s) via FLL; 424 minutes. Local airport times.
  • B61296: CUN 2026-12-04 16:55:00 → FLL 2026-12-04 18:45:00; layover at FLL: 129 minutes.
  • B6460: FLL 2026-12-04 20:54:00 → BDL 2026-12-04 23:59:00.

2026-11-27 → 2026-12-04 · $524.30

• United Airlines UA1764 / UA1677: BDL 2026-11-27 15:07:00 → CUN 2026-11-27 21:40:00; 1 stop(s) via IAD; 393 minutes. Local airport times.
  • UA1764: BDL 2026-11-27 15:07:00 → IAD 2026-11-27 16:30:00; layover at IAD: 77 minutes.
  • UA1677: IAD 2026-11-27 17:47:00 → CUN 2026-11-27 21:40:00.
• United Airlines UA1133 / UA274: CUN 2026-12-04 16:55:00 → BDL 2026-12-04 23:59:00; 1 stop(s) via IAD; 424 minutes. Local airport times.
  • UA1133: CUN 2026-12-04 16:55:00 → IAD 2026-12-04 20:19:00; layover at IAD: 132 minutes.
  • UA274: IAD 2026-12-04 22:31:00 → BDL 2026-12-04 23:59:00.

2026-11-27 → 2026-12-04 · $535.70

• Delta Air Lines DL2233 / DL592: BDL 2026-11-27 08:00:00 → CUN 2026-11-27 15:07:00; 1 stop(s) via ATL; 427 minutes. Local airport times.
  • DL2233: BDL 2026-11-27 08:00:00 → ATL 2026-11-27 10:42:00; layover at ATL: 96 minutes.
  • DL592: ATL 2026-11-27 12:18:00 → CUN 2026-11-27 15:07:00.
• United Airlines UA1133 / UA274: CUN 2026-12-04 16:55:00 → BDL 2026-12-04 23:59:00; 1 stop(s) via IAD; 424 minutes. Local airport times.
  • UA1133: CUN 2026-12-04 16:55:00 → IAD 2026-12-04 20:19:00; layover at IAD: 132 minutes.
  • UA274: IAD 2026-12-04 22:31:00 → BDL 2026-12-04 23:59:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

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Cheapest places in May from other cities

Fares observed October 24 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

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• This page: Cheapest places to fly from Hartford in May. Where to fly from Hartford 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.
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