Your travel platformSkip navigation

Scan the QR code and download our app

Tanie loty

Flights Chicago Puerto Rico

Special flight deals from Chicago to Puerto Rico

Why book flights with eSky?

Largest choice of flights

With flights from over 500 airlines, we'll find your perfect match in seconds.

Flexible search

Extend your search to include nearby airports and flex your dates for the cheapest deals.

Excellent products and services

Need travel insurance, cancellation insurance, car hire, local attraction bookings or more? We have you covered.

Over 4950 customer reviews - choose proven quality and book with complete confidence.

Find the best time to book cheap flights to San Juan

Flexible on travel dates? Discover the cheapest month to fly to San Juan

  • Cheapest round-trip flight

    from €124

  • Cheapest month to travel

    May

  • The cheapest day to fly

    Friday

  • Lowest prices

    1 day before
Apr
??
May
€124
Jun
€257
Jul
€199
Aug
€193
Sept
€334
Oct
€390
Nov
€397
Dec
€466
Jan
€390
Feb
€390
Mar
??

When is the best time to buy flight tickets?

Find out how far in advance it's worth booking round-trip flights.

  • 3 months before

    from

    €422

  • 1 day before

    from

    €322

Discover the cheapest day to fly

Discover on which day of the week flights are usually the most affordable.
??
Mon
€471
Tue
€389
Wed
??
Thu
€375
Fri
??
Sat
??
Sun

General information

  • Local time (UTC-4) in San Juan

  • Flight time from Chicago

  • Exchange Rate

    1 USD = 0.85 EUR
Puerto Rico
Puerto Rico is a territory in the Caribbean Sea belonging to the United States. The island forms part of the Greater Antilles and is dominated by the Cordillera Central mountains, including its highest peak, Cerro de Punta (1,338 m). Thanks to its humid subtropical climate, average temperatures hover around 26 °C year-round. Visitors can enjoy diverse wildlife and remnants of tropical forests. The best time to visit is during the dry season, from December to April, when rainfall is at its lowest.

Flights to Puerto Rico. These destinations top the list

Hey, good to see you!

Log in to see your booking details and book your next trip faster

By logging in or creating an account, you agree to our <a href="/terms-and-conditions" target="_blank">Terms & Conditions</a> and <a href='/privacy-policy' target='_blank'>Privacy Policy</a>.
eSky.eu is the administrator of your data. We will use it to process your bookings, assist you if necessary, and keep you informed about attractive prices. You can access and amend your data at any time.
or
or

Check booking status

To view your booking without logging in, enter your booking number and the email address used to make the reservation.

Don't have an account yet?Register