Find yourself in the Caribbean with this cheap fare to San Juan, and save up to $125 on the usual cost of a roundtrip ticket! American Airlines and JetBlue have discounted the fares from Chicago to just $276-$285 roundtrip.

The $276 fare is nonstop, while the rest requires 1 stop. These fares are available through June, and include travel over Thanksgiving, MLK Day, Presidents Day and Memorial Day. Travel is also widely available in March, perfect for your spring break getaway!

Fly.com Fare Calendar:

All flights are roundtrip, including tax:

Note:

  • American charges $25 for the first checked bag.
  • JetBlue charges $20-$25 for the first checked bag.
  • For more baggage information click here.

Savings:

  • Save up to $125 on typical roundtrip pricing

Travel Dates:

  • Oct. 24 – Dec. 13 & Jan. 9 – June 14

Sample Screenshots:

Chicago-San Juan: Fly.com Search Results

Chicago-San Juan: Fly.com Search Results

Chicago-San Juan American Airlines Booking Page

Chicago-San Juan American Airlines Booking Page

Chicago-San Juan: Fly.com Search Results

Chicago-San Juan: Fly.com Search Results

Chicago-San Juan: JetBlue Booking Page

Chicago-San Juan: JetBlue Booking Page

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Featured Image: San Juan, Puerto Rico at Night (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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