Cheap Flights from Chicago to Caribbean | CHI to Caribbean Flights | Chicago to Caribbean Flights
Here are the best cheap flights found by other travelers from All airports (CHI) in Chicago, IL, USA to the most popular airports in Caribbean, searching on hundreds of websites.
Prices in US Dollars for round trips including taxes.
Updated on Thursday, May 21 2026, 14:09 EDT
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Hotel Deals in San Juan
Diamond Palace Hotel & Casino
2.5 Star Hotel at Guaranteed low rate - click for details
Hotel Address: 55 Condado Avenue San Juan. General Description: Affordable accommodations Close proximity to business district Close proximity to shopping district Close proximity to major attractions Great combination for business and pleasure Location: Conveniently located in the Condado area Easy access to the beach Local Attractions: City entertainment in close proximity airport - 15 ...
Miramar
3 Star Hotel at Guaranteed low rate - click for details
Hotel Address: 606 Ponce de Leon Ave San Juan. General Description: Affordable accommodations Boutique hotel accommodations Located next to Condado Beach Close proximity to historic district Close proximity to major attractions Great combination for business and pleasure Location: Easy access to convention center Centrally located minutes from Condado Lagoon Local Attractions: Old San Juan ...
Tryp Macarena Hotel
4 Star Hotel at Guaranteed low rate - click for details
Hotel Address: San Juan de Ribera, 2 Seville. General Description: 4 star accommodations Close proximity to airport Close proximity to major attractions Great combination for business and pleasure Location: Located in suburban Seville next to the Guadalquivir river. Major attractions are nearby Local Attractions: Close to local attractions such as Isla Magica Theme Park, Museum of Modern Arts ...
Sidi San Juan Hotel
5 Star Hotel at Guaranteed low rate - click for details
Hotel Address: Calle Doblada 8, Playa de San Juan Alicante. General Description: Beautiful views and exceptional service Location: Conveniently located in San Juan beach Local Attractions: Close to local attractions such as Santa Barbara castle Recreation: Relaxing full service spa Organized children's activities Indoor swimming pool Restaurants & Lounges: Onsite restaurant Services: Shuttl ...
Sidi San Juan Hotel
5 Star Hotel at Guaranteed low rate - click for details
Hotel Address: Calle Doblada 8, Playa de San Juan Alicante. General Description: Beautiful views and exceptional service Location: Conveniently located in San Juan beach Local Attractions: Close to local attractions such as Santa Barbara castle Recreation: Relaxing full service spa Organized children's activities Indoor swimming pool Restaurants & Lounges: Onsite restaurant Services: Shuttl ...
Gran Melia Puerto Rico Hotel
5 Star Hotel at Guaranteed low rate - click for details
Hotel Address: 200 Coco Beach Boulevard San Juan. General Description 5 star accommodations Full service resort Beachfront accommodations Ideal accommodations for a vacation getaway Location Conveniently located in Rio Grande Perfectly located in beautiful Coco Beach Local Attractions downtown Rio Grande - 5 kilometers Jose Hernandez Poster Museum - 5 kilometers El Yunque ...
San Juan Inn & Trading Post
2 Star Hotel at Guaranteed low rate - click for details
Hotel Address: US HIGHWAY 163 & SAN JUAN. The hotel has an authentic trading post, which offers an extensive collection of traditional Navajo arts and crafts. It boasts partnerships with trusted tour guides who will assure you experience the best the area has to offer. ...