Vacations from Chicago to San Juan
Explore our popular vacation packages from San Jose, CR From - To
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Ponce Plaza Hotel Casino
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,627 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Aquarius Vacation Club At Boqueron Beach Resort
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,666 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Romeo Gay Hotel
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,677 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Red Door Inn
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,752 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Abitta Condado by IHG
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,772 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Patio Elba Boutique Hotel
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,810 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
The Condado Plaza
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,840 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Alma San Juan
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $1,864 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
AC Hotel by Marriott San Juan Condado
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $2,037 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Hotel Rumbao, a Tribute Portfolio Hotel
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $2,078 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Sheraton Puerto Rico Resort & Casino
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $2,420 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Caribe Hilton
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $2,676 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
La Concha Resort, Puerto Rico, Autograph Collection
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $3,694 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Hyatt Regency Grand Reserve
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $3,916 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
7 night(s)
Wyndham Grand Rio Mar Rainforest Beach&Golf Resort
12/21/2025 December 21, 2025
- 12/28/2025 December 28, 2025
Chicago (ORD) To San Juan (SJU)
Flight + Hotel
from $5,356 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 19 hours ago
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*Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays. Prices displayed have been collected within the last 24 hrs and may no longer be available at time of booking. Modifying this information may result in a different price. To find the most updated price, please visit aavacations.com.
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