The US, Caribbean and Central America 🌎 in $90s-$440s RT

The US, Caribbean and Central America 🌎 in $90s-$440s RT

We've been seeing a ton of international fares this week, but sometimes you want to stay a little closer to home. Luckily, JetBlue is here with some sweet not-officially-Black-Friday-but-they-dropped-on-Black-Friday discounts right here in our own backyard.

A huge chunk of this bundle is made up of routes all over the eastern US—hello, Martha's Vineyard! And if you're looking for something more exciting than Worcester (pronounced "wuh-ster," by the way) but still kinda close by, we've also got a bunch of flights to the Caribbean and Central America.

Just remember: what happens in the Virgin Islands, stays in the Virgin Islands :-)

Taking off ✈

Tip Published: Nov 28, 2025

Round trips from Atlanta (ATL):

  • Boston (BOS) - $167
  • Grand Cayman (GCM) - $252
Round trips from Boston (BOS):

  • Atlanta (ATL) - $167
  • Buffalo (BUF) - $139
  • Charleston (CHS) - $137 (peak summer)
  • Chicago O'Hare (ORD) - $127 (peak summer)
  • Cleveland (CLE) - $157
  • Daytona Beach (DAB) - $167
  • Denver (DEN) - $187
  • Destin (VPS) - $196
  • Detroit (DTW) - $167
  • Fort Lauderdale (FLL) - $197 (peak summer)
  • Fort Myers (RSW) - $147
  • Jacksonville (JAX) - $117
  • Los Angeles (LAX) - $171
  • Martha's Vineyard (MVY) - $205 (peak summer)
  • Milwaukee (MKE) - $187
  • Nantucket (ACK) - $185 (peak summer)
  • New Orleans (MSY) - $167
  • New York (JFK) - $117
  • Orlando (MCO) - $127
  • Philadelphia (PHL) - $127 (peak summer)
  • Phoenix (PHX) - $197
  • Pittsburgh (PIT) - $147 (peak summer)
  • Providenciales (PLS) - $344
  • Raleigh (RDU) - $137
  • Richmond (RIC) - $147 (peak summer)
  • Savannah (SAV) - $167 (peak summer)
  • Syracuse (SYR) - $99 (peak summer)
  • Tampa (TPA) - $147
  • West Palm Beach (PBI) - $177
  • Wilmington (ILM) - $182 (peak summer)
Round trips from Chicago O'Hare (ORD):

  • Boston (BOS) - $147 (peak summer)
  • Bridgetown (BGI) - $322
  • New York (JFK) - $138
  • San Juan (SJU) - $150
  • Santiago (STI) - $256
Round trips from Denver (DEN):

  • Bermuda (BDA) - $427
  • Santiago (STI) - $372
  • Santiago (STI) - $372
Round trips from Fort Lauderdale (FLL):

  • Albany (ALB) - $172
  • Bermuda (BDA) - $443
  • Boston (BOS) - $197 (peak summer)
  • Budapest (BUD) - $127
  • Hartford (BDL) - $172 (peak summer)
  • Islip (ISP) - $147
  • Los Angeles (LAX) - $237
  • Manchester Boston (MHT) - $177
  • New York (JFK) - $127
  • New York LaGuardia (LGA) - $127
  • Newark (EWR) - $127
  • Norfolk (ORF) - $105
  • Phoenix (PHX) - $164
  • Pittsburgh (PIT) - $123
  • Providence (PVD) - $157
  • Raleigh (RDU) - $127 (peak summer)
  • Richmond (RIC) - $137 (peak summer)
  • San Francisco (SFO) - $203
  • Washington Reagan (DCA) - $117
  • White Plains (HPN) - $147
  • Worcester (ORH) - $215 (peak summer)
Round trips from Houston (IAH):

  • Boston (BOS) - $237
Round trips from Las Vegas (LAS):

  • Boston (BOS) - $207
  • New York (JFK) - $178
  • Newark (EWR) - $197
  • Orlando (MCO) - $237
Round trips from Los Angeles (LAX):

  • Boston (BOS) - $171
  • Buffalo (BUF) - $307 (peak summer)
  • Fort Lauderdale (FLL) - $237
  • Hartford (BDL) - $347
  • Nassau (NAS) - $363
  • New York (JFK) - $216
  • Port of Spain (POS) - $337
  • Sint Maarten (SXM) - $367
  • West Palm Beach (PBI) - $281
Round trips from New York (JFK):

  • Aguadilla (BQN) - $244
  • Atlanta (ATL) - $113
  • Bermuda (BDA) - $384
  • Buffalo (BUF) - $127
  • CancĂșn (CUN) - $287
  • Daytona Beach (DAB) - $127
  • Denver (DEN) - $207
  • Destin (VPS) - $186 (peak summer)
  • Detroit (DTW) - $137
  • Fort Lauderdale (FLL) - $147
  • Fort Myers (RSW) - $147
  • Guatemala City (GUA) - $217
  • Jacksonville (JAX) - $137
  • Las Vegas (LAS) - $178
  • Los Angeles (LAX) - $216
  • Montego Bay (MBJ) - $325
  • Nantucket (ACK) - $207 (peak summer)
  • Nashville (BNA) - $127
  • Phoenix (PHX) - $199
  • Pittsburgh (PIT) - $131 (peak summer)
  • Portland (PWM) - $127
  • Providence (PVD) - $91
  • Providenciales (PLS) - $334
  • Raleigh (RDU) - $132
  • Rochester (ROC) - $137 (peak summer)
  • San Francisco (SFO) - $205
  • Savannah (SAV) - $147
  • Syracuse (SYR) - $137
  • Tampa (TPA) - $157
Round trips from New York LaGuardia (LGA):

  • Fort Lauderdale (FLL) - $147
  • Nantucket (ACK) - $207 (peak summer)
  • Tampa (TPA) - $157 (peak summer)
  • West Palm Beach (PBI) - $147 (peak summer)
Round trips from Newark (EWR):

  • CancĂșn (CUN) - $287
  • Fort Lauderdale (FLL) - $147
  • Fort Myers (RSW) - $167 (peak summer)
  • Las Vegas (LAS) - $197
  • Orlando (MCO) - $95
  • Tampa (TPA) - $157 (peak summer)
  • West Palm Beach (PBI) - $147 (peak summer)
Round trips from Orlando (MCO):

  • Aguadilla (BQN) - $212
  • Albany (ALB) - $197
  • Bermuda (BDA) - $449
  • Buffalo (BUF) - $207
  • CancĂșn (CUN) - $287
  • Hartford (BDL) - $197 (non-stop, peak summer)
  • Islip (ISP) - $119 (non-stop)
  • Las Vegas (LAS) - $237
  • Manchester Boston (MHT) - $217
  • Ponce (PSE) - $212 (peak summer)
  • Providence (PVD) - $157 (non-stop)
  • Richmond (RIC) - $127 (peak summer)
  • San Juan (SJU) - $244 (peak summer)
  • Syracuse (SYR) - $197
  • Washington Reagan (DCA) - $107
  • White Plains (HPN) - $187 (peak summer)
  • Worcester (ORH) - $185 (non-stop, peak summer)
Round trips from Philadelphia (PHL):

  • Aruba (AUA) - $302
  • Boston (BOS) - $127 (peak summer)
  • Fort Lauderdale (FLL) - $69
  • Guatemala City (GUA) - $249
  • Montego Bay (MBJ) - $327
Round trips from Phoenix (PHX):

  • Boston (BOS) - $197
  • Fort Lauderdale (FLL) - $203
  • Nassau (NAS) - $371
  • New York (JFK) - $199
  • Port of Spain (POS) - $379
Round trips from San Diego (SAN):

  • New York (JFK) - $247
Round trips from San Francisco (SFO):

  • Boston (BOS) - $227
  • Curaçao (CUR) - $354
  • Fort Lauderdale (FLL) - $217
  • New York (JFK) - $205
Round trips from Tampa (TPA):

  • Bermuda (BDA) - $439
  • Boston (BOS) - $147
  • Hartford (BDL) - $187
  • Islip (ISP) - $162
  • New York (JFK) - $147
  • New York LaGuardia (LGA) - $147
  • Newark (EWR) - $157
  • Punta Cana (PUJ) - $329
  • White Plains (HPN) - $167
Round trips from Washington Reagan (DCA):

  • Bermuda (BDA) - $421
  • Boston (BOS) - $137
  • Fort Lauderdale (FLL) - $132
  • Martha's Vineyard (MVY) - $207 (peak summer)
  • Nantucket (ACK) - $207 (peak summer)
  • New York (JFK) - $117
  • Orlando (MCO) - $122
  • Saint Lucia (UVF) - $241
  • Saint Thomas (STT) - $209
  • San Juan (SJU) - $242
  • West Palm Beach (PBI) - $157 (peak summer)
Round trips from West Palm Beach (PBI):

  • Boston (BOS) - $237 (peak summer)
  • Hartford (BDL) - $177 (peak summer)
  • Islip (ISP) - $157
  • Los Angeles (LAX) - $281
  • New York (JFK) - $127
  • New York LaGuardia (LGA) - $127
  • Newark (EWR) - $127
  • Washington Reagan (DCA) - $157
  • White Plains (HPN) - $147
Flight Details

Travel Dates

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Airline

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Standard Fare

$300 - $600

Bags & Fees

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Flight Notes

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How to Book

    This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.