US cities to the Caribbean or Central America from only $149 roundtrip (Nov-Mar dates)

_Belize City / _Cancun / _Liberia / _Puerto Vallarta / _San Jose / _San Jose del Cabo / _San Juan / 1 Stop / Austin / Austin, USA → Belize City, Belize / Austin, USA → Cancun, Mexico / Austin, USA → Liberia, Costa Rica / Austin, USA → Puerto Vallarta, Mexico / Austin, USA → San Jose del Cabo, Mexico / Austin, USA → San Jose, Costa Rica / Austin, USA → San Juan, Puerto Rico / Austin, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Austin, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Austin, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Austin, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Austin, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Baltimore / Baltimore, USA → Belize City, Belize / Baltimore, USA → Cancun, Mexico / Baltimore, USA → Liberia, Costa Rica / Baltimore, USA → Puerto Vallarta, Mexico / Baltimore, USA → San Jose del Cabo, Mexico / Baltimore, USA → San Jose, Costa Rica / Baltimore, USA → San Juan, Puerto Rico / Baltimore, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Baltimore, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Baltimore, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Baltimore, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Baltimore, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Caribbean / Central America / Chicago / Chicago, USA → Belize City, Belize / Chicago, USA → Cancun, Mexico / Chicago, USA → Liberia, Costa Rica / Chicago, USA → Puerto Vallarta, Mexico / Chicago, USA → San Jose del Cabo, Mexico / Chicago, USA → San Jose, Costa Rica / Chicago, USA → San Juan, Puerto Rico / Chicago, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Chicago, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Chicago, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Chicago, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Chicago, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Dallas / Dallas, USA → Belize City, Belize / Dallas, USA → Cancun, Mexico / Dallas, USA → Liberia, Costa Rica / Dallas, USA → Puerto Vallarta, Mexico / Dallas, USA → San Jose del Cabo, Mexico / Dallas, USA → San Jose, Costa Rica / Dallas, USA → San Juan, Puerto Rico / Dallas, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Dallas, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Dallas, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Dallas, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Dallas, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Denver / Denver, USA → Belize City, Belize / Denver, USA → Cancun, Mexico / Denver, USA → Liberia, Costa Rica / Denver, USA → Puerto Vallarta, Mexico / Denver, USA → San Jose del Cabo, Mexico / Denver, USA → San Jose, Costa Rica / Denver, USA → San Juan, Puerto Rico / Denver, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Denver, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Denver, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Denver, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Denver, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Depart USA / Economy / Flight / Fort Lauderdale / Fort Lauderdale, USA → Belize City, Belize / Fort Lauderdale, USA → Cancun, Mexico / Fort Lauderdale, USA → Liberia, Costa Rica / Fort Lauderdale, USA → Puerto Vallarta, Mexico / Fort Lauderdale, USA → San Jose del Cabo, Mexico / Fort Lauderdale, USA → San Jose, Costa Rica / Fort Lauderdale, USA → San Juan, Puerto Rico / Fort Lauderdale, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Fort Lauderdale, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Fort Lauderdale, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Fort Lauderdale, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Fort Lauderdale, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Houston / Houston, USA → Belize City, Belize / Houston, USA → Cancun, Mexico / Houston, USA → Liberia, Costa Rica / Houston, USA → Puerto Vallarta, Mexico / Houston, USA → San Jose del Cabo, Mexico / Houston, USA → San Jose, Costa Rica / Houston, USA → San Juan, Puerto Rico / Houston, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Houston, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Houston, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Houston, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Houston, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Indianapolis / Indianapolis, USA → Belize City, Belize / Indianapolis, USA → Cancun, Mexico / Indianapolis, USA → Liberia, Costa Rica / Indianapolis, USA → Puerto Vallarta, Mexico / Indianapolis, USA → San Jose del Cabo, Mexico / Indianapolis, USA → San Jose, Costa Rica / Indianapolis, USA → San Juan, Puerto Rico / Indianapolis, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Indianapolis, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Indianapolis, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Indianapolis, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Indianapolis, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Kansas City / Kansas City, USA → Belize City, Belize / Kansas City, USA → Cancun, Mexico / Kansas City, USA → Liberia, Costa Rica / Kansas City, USA → Puerto Vallarta, Mexico / Kansas City, USA → San Jose del Cabo, Mexico / Kansas City, USA → San Jose, Costa Rica / Kansas City, USA → San Juan, Puerto Rico / Kansas City, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Kansas City, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Kansas City, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Kansas City, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Kansas City, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Los Angeles / Los Angeles, USA → Belize City, Belize / Los Angeles, USA → Cancun, Mexico / Los Angeles, USA → Liberia, Costa Rica / Los Angeles, USA → Puerto Vallarta, Mexico / Los Angeles, USA → San Jose del Cabo, Mexico / Los Angeles, USA → San Jose, Costa Rica / Los Angeles, USA → San Juan, Puerto Rico / Los Angeles, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Los Angeles, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Los Angeles, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Los Angeles, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Los Angeles, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Nashville / Nashville, USA → Belize City, Belize / Nashville, USA → Cancun, Mexico / Nashville, USA → Liberia, Costa Rica / Nashville, USA → Puerto Vallarta, Mexico / Nashville, USA → San Jose del Cabo, Mexico / Nashville, USA → San Jose, Costa Rica / Nashville, USA → San Juan, Puerto Rico / Nashville, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Nashville, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Nashville, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Nashville, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Nashville, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / New Orleans / New Orleans, USA → Belize City, Belize / New Orleans, USA → Cancun, Mexico / New Orleans, USA → Liberia, Costa Rica / New Orleans, USA → Puerto Vallarta, Mexico / New Orleans, USA → San Jose del Cabo, Mexico / New Orleans, USA → San Jose, Costa Rica / New Orleans, USA → San Juan, Puerto Rico / New Orleans, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / New Orleans, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / New Orleans, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / New Orleans, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / New Orleans, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Non-Stop / Oakland / Oakland, USA → Belize City, Belize / Oakland, USA → Cancun, Mexico / Oakland, USA → Liberia, Costa Rica / Oakland, USA → Puerto Vallarta, Mexico / Oakland, USA → San Jose del Cabo, Mexico / Oakland, USA → San Jose, Costa Rica / Oakland, USA → San Juan, Puerto Rico / Oakland, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Oakland, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Oakland, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Oakland, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Oakland, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Orlando / Orlando, USA → Belize City, Belize / Orlando, USA → Cancun, Mexico / Orlando, USA → Liberia, Costa Rica / Orlando, USA → Puerto Vallarta, Mexico / Orlando, USA → San Jose del Cabo, Mexico / Orlando, USA → San Jose, Costa Rica / Orlando, USA → San Juan, Puerto Rico / Orlando, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Orlando, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Orlando, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Orlando, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Orlando, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Phoenix / Phoenix, USA → Belize City, Belize / Phoenix, USA → Cancun, Mexico / Phoenix, USA → Liberia, Costa Rica / Phoenix, USA → Puerto Vallarta, Mexico / Phoenix, USA → San Jose del Cabo, Mexico / Phoenix, USA → San Jose, Costa Rica / Phoenix, USA → San Juan, Puerto Rico / Phoenix, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Phoenix, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Phoenix, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Phoenix, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Phoenix, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / San Antonio / San Antonio, USA → Belize City, Belize / San Antonio, USA → Cancun, Mexico / San Antonio, USA → Liberia, Costa Rica / San Antonio, USA → Puerto Vallarta, Mexico / San Antonio, USA → San Jose del Cabo, Mexico / San Antonio, USA → San Jose, Costa Rica / San Antonio, USA → San Juan, Puerto Rico / San Antonio, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / San Antonio, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / San Antonio, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / San Antonio, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / San Antonio, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Seattle / Seattle, USA → Belize City, Belize / Seattle, USA → Cancun, Mexico / Seattle, USA → Liberia, Costa Rica / Seattle, USA → Puerto Vallarta, Mexico / Seattle, USA → San Jose del Cabo, Mexico / Seattle, USA → San Jose, Costa Rica / Seattle, USA → San Juan, Puerto Rico / Seattle, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Seattle, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Seattle, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Seattle, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Seattle, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Southwest Airlines / Standard Route / Tampa / Tampa, USA → Belize City, Belize / Tampa, USA → Cancun, Mexico / Tampa, USA → Liberia, Costa Rica / Tampa, USA → Puerto Vallarta, Mexico / Tampa, USA → San Jose del Cabo, Mexico / Tampa, USA → San Jose, Costa Rica / Tampa, USA → San Juan, Puerto Rico / Tampa, USA → span class="yiv5734182106dm_accent"Grand Cayman, Cayman Islands / Tampa, USA → span class="yiv5734182106dm_accent"Montego Bay, Jamaica / Tampa, USA → span class="yiv5734182106dm_accent"Nassau, Bahamas / Tampa, USA → span class="yiv5734182106dm_accent"Providenciales, Turks and Caicos / Tampa, USA → span class="yiv5734182106dm_accent"Punta Cana, Dominican Republic / Trending
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Cheap flights from US cities to the Caribbean or Central America from only $149 roundtrip.

 

DEPART:
Fort Lauderdale/Chicago/Dallas/Houston/Kansas City/Nashville/New Orleans/San Antonio/Austin/Denver/Tampa/Baltimore/Indianapolis/Los Angeles/Orlando/Phoenix/Oakland/Seattle, USA

 

ARRIVE:
San Juan, Puerto Rico
Grand Cayman, Cayman Islands
Nassau, Bahamas
Providenciales, Turks and Caicos
Punta Cana, Dominican Republic
Montego Bay, Jamaica
San Jose del Cabo/Puerto Vallarta/Cancun, Mexico
San Jose/Liberia, Costa Rica
Belize City, Belize

 

RETURN:
Fort Lauderdale/Chicago/Dallas/Houston/Kansas City/Nashville/New Orleans/San Antonio/Austin/Denver/Tampa/Baltimore/Indianapolis/Los Angeles/Orlando/Phoenix/Oakland/Seattle, USA

 

DATES:
Availability from November 2023 to March 2024

 

The Southwest Airlines website allow you to search each month with a single click so there is no need for a list of example dates from us.

 

STOPS:
Various cities

 

AIRLINES:
Southwest Airlines

 

 

GO TO DEAL

 

 

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San Juan