Various Airlines Round-Trip from US Cities to the Caribbean Starting at $209

Looking for an adventure of a life time? If you live in one of  then you are in luck because you can get cheap flights to the Caribbean at an astounding price of $209 for round trip! There are several trusted airlines you can choose from such as American, JetBlue, Norwegian and United. Pick up a few bonus miles or spend a few to travel in luxury on your trip to the Caribbean with various membership programs these airlines offer. Travel dates are available from September to end of the year but don’t wait too long to book your trip because flight deals go fast!

We recommend you look up your preferred dates on Google Flights in case there is a cheaper price than the ones we listed. Depending when you book, the prices can change! (YMMV) The airline fares rule associated with your flight and be reviewed over pre-purchase, on your contract, and post purchase with the itinerary displayed on their website, be sure you read their full terms before making your purchase.

Flights from New York City to San Juan

• Book Now!
• Promotion: Round-trip from New York City, NY to Port of San Juan for $209.

Flights from Chicago to Cancun

• Book Now!
• Promotion: Round-trip from Chicago, IL to Cancun, Mexico for $219.

Flights from Washington to San Jose

• Book Now!
• Promotion: Round-trip from Washington, DC to San Jose for $299.

• Note: Valid for travel on the outbound from March – June 2019.

Get East Coast to Caribbean Flight Deals

1. Use Google Flights to check the flights and times that fit best for you. (YMMV)
2. To earn cash back we highly recommend using the above, Best Airline Flight Credit Cards to save the most money.
3. Once you found the times that you would like to make sure you book it early so that it doesn’t change.

Bottom Line

Take advantage of this great opportunity for a cheap getaway trip at one of many warm beaches in the Caribbean. The earlier you start planning for this trip the earlier you can get started on your vacation. Travel to exotic and unique places in the world and experience something new.

US citizens should visit the US Passports & International Travel website for the latest information, including exercising safety abroad and entry requirements. This is the cheapest fare I found but please let us know if you got anything different! If you want more Cheap Flight Deals, check out our master list!

	Chase Business Complete Checking®: Earn $300 or $500 when you open a new Chase Business Complete Checking® account. For new Chase business checking customers with qualifying activities. Chase offers financial products and services that let you bank when and how you want. Get Coupon---Chase Business Checking Review
	Huntington Unlimited Business Checking: Earn $400 bonus when you open a Huntington Unlimited Business Checking account and make total deposits of at least $5,000 within 60 days of account opening. The $400 bonus will be deposited into your account after all requirements are met. This account is for businesses with higher checking activity and greater cash flow needs. Apply Now---Huntington Unlimited Business Checking Review
	U.S. Bank Business Checking: Earn a $400 bonus when you open a U.S. Bank Business Essentials Account or $1,000 when you open a Platinum Business Checking Account online with promo code Q3AFL25 and complete qualifying activities, subject to certain terms and limitations. Offer valid through September 30, 2025. Member FDIC. Apply Now---U.S. Bank Business Checking Review
	Bank of America Business Advantage Checking Bonus Offer Open a new Bank of America Business Advantage checking account and complete the eligible requirements to earn a $200 cash bonus offer. See offer page for more details. Additional terms and conditions apply. See offer page for more details. Learn More---Bank of America Business Checking Review