San Jose (Costa Rica) vacation packages
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cmp-carousel-container-explain 7 night(s)
Hotel Milan Costa Rica
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $761 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Casa Roland San José
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $864 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Sabana Studios
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $952 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Sleep Inn Paseo Las Damas
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,014 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Delta Hotels by Marriott San Jose Aurola
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $947 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hotel Palma Real
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $978 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Apartotel & Suites Villas del Rio
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,005 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
D Sabana Hotel
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,115 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Wyndham Garden San Jose Escazu
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,040 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Holiday Inn Express San Jose Costa Rica Airport
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,083 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Parque Del Lago Boutique Hotel
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,004 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Gran Hotel Costa Rica Curio Collection by Hilton
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,090 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Casa Turire Hotel & Restaurante
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,098 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Presidente
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,114 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Sheraton San Jose Hotel, Costa Rica
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,253 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Xandari Resort & Spa
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,280 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Holiday Inn San Jose La Sabana
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,288 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Real InterContinental at Multiplaza Mall
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,613 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
The Retreat Costa Rica
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $2,127 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
El Silencio Lodge & Spa
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $3,817 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hotel Don Ernesto by La Chimba
10/14/2025 October 14, 2025
- 10/21/2025 October 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $992 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Hotel Don Ernesto by La Chimba
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $962 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
DoubleTree by Hilton Cariari San Jose
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,166 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Hyatt Centric San José Escazú
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,284 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Hotel Milan Costa Rica
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $832 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Casa Roland San José
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $958 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Sabana Studios
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,065 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Sleep Inn Paseo Las Damas
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,162 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Delta Hotels by Marriott San Jose Aurola
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $996 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Hotel Palma Real
12/14/2025 December 14, 2025
- 12/21/2025 December 21, 2025
Chicago (ORD) To San Jose (Costa Rica) (SJO)
Flight + Hotel
from $1,164 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
*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.