End your summer in paradise! Flights to the Caribbean islands of Puerto Rico and St. Thomas in late summer are now up to $150 less than the usual cost. American Airlines and United Airlines have dropped the price of airfares from Chicago to San Juan and Charlotte Amalie to just $274-$289 roundtrip, including tax.

Travel in August and September, including over Labor Day weekend.

Fly.com Fare Calendars

Flights from Chicago to the Caribbean (all flights are roundtrip, including tax):

Note:

  • American & United charge $25 for the first checked bag.
  • For more baggage information click here.

Savings:

  • Up to $150 OFF the usual cost

Travel Dates:

  • To San Juan:Aug. 24 to Sept. 28
  • To Charlotte Amalie: Aug. 10 to Sept. 24
  • Includes travel over Labor Day weekend

Sample Screenshots:

CHI-SJU: Fly.com Search Results

CHI-SJU: Fly.com Search Results

CHI-SJU: United Airlines Booking Page

CHI-SJU: United Airlines Booking Page

CHI-STT: Fly.com Search Results

CHI-STT: Fly.com Search Results

CHI-STT: American Airlines Booking Page

CHI-STT: American Airlines Booking Page

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Featured Image: Isla Verde Beach, San Juan (Shutterstock.com)

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Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!

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