$274-$289 — Chicago to 2 Caribbean Islands (R/T)

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

Fly.com Updates

Here are a few ways to stay connected with us:

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

Comments are closed.