JetBlue has round-trip flights from New York (JFK) to Grand Cayman (GCM) for $246, NONSTOP. Flights February to April. Very few weekends available.
JetBlue’s “Basic” fares allow for a carry-on bag and a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.
JetBlue has round-trip flights from Seattle (SEA) to Grand Cayman (GCM) for $433-$448 with a connection. Flights November to December. Departures on Friday and Sunday. Very few weekends available. Origin/Destination reversible. Holiday blackouts.
Flight is an overnight “Red-Eye”.
JetBlue and Delta have round-trip flights from Denver (DEN) to Grand Cayman or Saint Lucia (GCM) for $377-$441 with a connection. Grand Cayman flights August to May. Saint Lucia flights September to April. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday. Extended weekends available. Origin/Destination reversible.
JetBlue’s “Basic” fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the “first free checked bag” perk.
JetBlue has round-trip flights from Phoenix (PHX) to Grand Cayman (GCM) for $357 with a connection. Flights in August. Departures on Monday, Tuesday, Wednesday, Thursday, and Sunday. No Fridays or Saturdays. Very few extended weekends available. Origin/Destination reversible.
JetBlue’s “Basic” fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the “first free checked bag” perk.
American Airlines has round-trip flights from New York/Newark (LGA/EWR) to Grand Cayman (GCM) for $231-$238 with a connection. Flights July to April. Weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Delta has round-trip flights from Chicago (ORD/MDW) to Grand Cayman (GCM) for $255 with a connection. Flights in March. No Saturday departures. Very few weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on Delta. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
JetBlue has round-trip flights from New York (JFK) to Grand Cayman, Belize, Costa Rica, Curacao, or Guatemala City (GCM, BZE, LIR, CUR, GUA) for $227-$349, NONSTOP. Flights February to May. No last minute fares available. Origin/Destination reversible.
JetBlue’s “Basic” fares only allow a small personal item (17 x 13 x 8 inches), like a Jansport SuperBreak backpack without a fee. A regular sized carry-on bag will incur a bag fee. To avoid bag fees, consider using a credit card with the “first free checked bag” perk.
American Airlines has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $326-$333 with a connection. Flights January to May. Departures on Tuesday and Wednesday. Origin/Destination reversible.
Hopper has a Cyber Monday coupon for -$200 off Cayman Hotels.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Hopper has a $100 off coupon for Cayman Islands.
American Airlines has round-trip flights from Denver (DEN) to Grand Cayman (GCM) for $332-$353 with a connection. If you apply the Hopper coupon, the cost of the round-trip is about $237-$258. Flights August to April. Very few weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Most domestic carriers have round-trip flights from Chicago or Milwaukee (ORD, MDW, MKE) to various destinations in Hawaii, the Caribbean, Central America, or Mexico for $177-$408, NONSTOP or with a connection. Dates vary, you’ll need to look at the linked Calendar. Origin/Destination reversible. No Major Holiday dates available. We believe most of these discount fares will end after 06/15/2023.
Noteworthy destinations in this list: San Juan ($177), Belize ($363), Honolulu ($376), Kahului ($376), Costa Rica ($408), and Grand Cayman ($294).
Hopper has a $100 off Cayman Islands coupon.
American Airlines has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $286-$289 with a connection. If you apply the Hopper coupon, the cost of the round-trip is about $188. Flights August to December. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible. No Christmas dates available.
Hopper has a $100 off Cayman Islands coupon.
United has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $384, NONSTOP. If you apply the Hopper coupon, the cost of the round-trip is about $284. Flights in October. Departures on Sunday.
This deal is very limited, it’s only available as a round-trip departing Oct 29, returning Nov 04, but at this price I think it is worth it to whomever picks it up.
Hopper has a $100 off Cayman Islands coupon.
American Airlines and Delta have round-trip flights from Los Angeles (LAX) to Grand Cayman (GCM) for $389 with a connection. If you apply the Hopper coupon, the cost of the round-trip is about $289. Flights July to March. Weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on Delta. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Hopper has a $100 off Cayman Islands coupon.
JetBlue has round-trip flights from New York (JFK) to Grand Cayman (GCM) for $256, NONSTOP. If you apply the Hopper coupon, the cost of the round-trip is about $156. Flights in June. Very few weekends available. Origin/Destination reversible.
United, American Airlines, and JetBlue have round-trip flights from New York/Newark (EWR/LGA/JFK) to Grand Cayman (GCM) for $266-$288, NONSTOP or with connections. Flights May to June. Weekends available. Origin/Destination reversible.
American Airlines, United, and Delta have round-trip flights from Milwaukee (MKE) to Grand Cayman (GCM) for $372-$408 with a connection. Flights March to May. Origin/Destination reversible.
United has round-trip flights from Newark/New York (EWR) to Grand Cayman (GCM) for $255-$265, NONSTOP. Flights in December. Very few weekends available. Origin/Destination reversible. Dates over Christmas are available.
JetBlue has round-trip flights from New York (JFK) to Grand Cayman (GCM) for $255, NONSTOP. Flights November to December. Extended weekends available. Origin/Destination reversible. Holiday blackouts.
American Airlines, Delta and United have round-trip flights from Milwaukee (MKE) to Grand Cayman (GCM) for $319-$326 with a connection. Flights December to February. No Wednesday departures. Very few weekends available. Origin/Destination reversible.
American Airlines has round-trip flights from Los Angeles (LAX) to Grand Cayman (GCM) for $353-$367, with a connection. Flights January, February, May, and June. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
