Head off on vacation to tropical Puerto Rico! Book United flights from Chicago to San Juan for $143 for a round trip with United!
Fancy a getaway to one of the Caribbean Islands? Jump at the chance to kick back on the beautiful beaches of Puerto Rico, enjoying rum, sun and crystal clear waters of the Caribbean Sea.
Highlights of San Juan
The capital of Puerto Rico is made up of historic buildings and exciting attractions. Delight walking on the 500-year-old city with its narrow, cobblestone streets, brightly colored buildings, bastions and powder houses. The walled city still preserves its stunning colonial architecture. Go to Paseo de la Princesca, a promenade where you can experience live music along with arts and crafts vendors. Castillo San Felipe del Morro is amazing fortress that has protected Puerto Rico for hundreds of years.
Castillo de San Cristobal is San Juan's second fortress, the largest stone fortification that the Spanish built in the New World. On weekends, you can take a guided tour in the underground passageways that are usually closed to the public.
Find out more about Puerto Rico in our guide: Destination Fly4free: Puerto Rico >>
Travel dates:
August – September 2023 (daily availability)
Route:
Chicago – San Juan – Chicago
Baggage allowance:
One personal item per passenger
Please note: All the information on this page is correct at the time of publication. If you are checking out the deal at a later date, the price and the availability may no longer be as advertised. Prices are subject to change. To ensure you never miss our deal again, sign up for DEAL ALERTS: download our App on Google Play or App Store. You can also opt for email notifications >> or Telegram alerts >>
Hotel $165/double
We suggest you staying in top-rated Hotel Villa del Sol with excellent reviews and free cancellation!
Car
If you plan to hire a car for your trip, we encourage you to book it on Kayak >>
eSIM
Traveling soon? Get your Holafly eSIM for unlimited internet access in any destination. No more worrying about roaming charges or finding local SIM cards. Enjoy unlimited data and stay connected with ease. Order your Holafly eSIM now »
Travel insurance
Heymondo offers a wide range of travel assistance insurance policies. They combine the best quality, service and price with various levels of coverage, so you’re covered on your weekend getaways and long trips. Buy insurance »
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