Flight + Hotel Packages from Chicago to San Jose, CR
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Number of Stars
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1/30
7Night(s) Trip
Barcelo San Jose
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ORD-SJO
Flights+Hotel
From
$725* Price subject to change
Viewed:5 hours ago
2/30
4Night(s) Trip
Hotel Cultura Plaza
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ORD-SJO
Flights+Hotel
From
$731* Price subject to change
Viewed:13 hours ago
3/30
7Night(s) Trip
La Bergerac Boutique Hotel
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ORD-SJO
Flights+Hotel
From
$801* Price subject to change
Viewed:5 hours ago
4/30
4Night(s) Trip
Doubletree By Hilton Cariari San Jose - Costa Rica
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ORD-SJO
Flights+Hotel
From
$813* Price subject to change
Viewed:13 hours ago
5/30
5Night(s) Trip
The Oaks Tamarindo Pool Front Condominiums fast wifi
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ORD-SJO
Flights+Hotel
From
$975* Price subject to change
Viewed:10 hours ago
6/30
5Night(s) Trip
Occidental Papagayo - Adults Only All Inclusive
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ORD-SJO
Flights+Hotel
From
$1,042* Price subject to change
Viewed:10 hours ago
7/30
5Night(s) Trip
Occidental Tamarindo All Inclusive
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ORD-SJO
Flights+Hotel
From
$1,169* Price subject to change
Viewed:10 hours ago
8/30
5Night(s) Trip
Hacienda Guachipelin Volcano Ranch Hotel & Hot Springs
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ORD-SJO
Flights+Hotel
From
$1,172* Price subject to change
Viewed:10 hours ago
9/30
5Night(s) Trip
Bahia Pez Vela Resort
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ORD-SJO
Flights+Hotel
From
$1,205* Price subject to change
Viewed:10 hours ago
10/30
5Night(s) Trip
Riu Guanacaste - All Inclusive
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ORD-SJO
Flights+Hotel
From
$1,319* Price subject to change
Viewed:10 hours ago
11/30
5Night(s) Trip
Hotel Tamarindo Diria Beach Resort
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ORD-SJO
Flights+Hotel
From
$1,407* Price subject to change
Viewed:10 hours ago
12/30
5Night(s) Trip
Riu Palace Costa Rica - All Inclusive
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ORD-SJO
Flights+Hotel
From
$1,475* Price subject to change
Viewed:10 hours ago
13/30
5Night(s) Trip
Planet Hollywood Costa Rica, An Autograph Collection All-Inclusive Resort
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ORD-SJO
Flights+Hotel
From
$1,516* Price subject to change
Viewed:10 hours ago
14/30
5Night(s) Trip
Jardin del Eden Boutique Hotel
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ORD-SJO
Flights+Hotel
From
$1,542* Price subject to change
Viewed:10 hours ago
15/30
5Night(s) Trip
JW Marriott Guanacaste Resort & Spa
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ORD-SJO
Flights+Hotel
From
$1,874* Price subject to change
Viewed:10 hours ago
16/30
5Night(s) Trip
The Westin Reserva Conchal, an All-Inclusive Golf Resort & Spa
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ORD-SJO
Flights+Hotel
From
$1,937* Price subject to change
Viewed:10 hours ago
17/30
5Night(s) Trip
W Costa Rica - Reserva Conchal
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ORD-SJO
Flights+Hotel
From
$2,027* Price subject to change
Viewed:10 hours ago
18/30
5Night(s) Trip
Epic Tamarindo Boutique Hotel
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ORD-SJO
Flights+Hotel
From
$2,034* Price subject to change
Viewed:10 hours ago
19/30
5Night(s) Trip
Secrets Papagayo All Inclusive - Adults Only
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ORD-SJO
Flights+Hotel
From
$2,159* Price subject to change
Viewed:10 hours ago
20/30
3Night(s) Trip
Hotel Milan Costa Rica
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ORD-SJO
Flights+Hotel
From
$711* Price subject to change
Viewed:a day ago
21/30
3Night(s) Trip
Four Points by Sheraton San Jose Costa Rica
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ORD-SJO
Flights+Hotel
From
$750* Price subject to change
Viewed:a day ago
22/30
3Night(s) Trip
Urban Green Hotel & Suites
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ORD-SJO
Flights+Hotel
From
$755* Price subject to change
Viewed:a day ago
23/30
3Night(s) Trip
Crowne Plaza San Jose La Sabana By IHG
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ORD-SJO
Flights+Hotel
From
$783* Price subject to change
Viewed:a day ago
24/30
3Night(s) Trip
Radisson San Jose-Costa Rica
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ORD-SJO
Flights+Hotel
From
$797* Price subject to change
Viewed:a day ago
25/30
3Night(s) Trip
Sheraton San Jose Hotel, Costa Rica
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ORD-SJO
Flights+Hotel
From
$818* Price subject to change
Viewed:a day ago
26/30
3Night(s) Trip
Gran Hotel Costa Rica, Curio Collection By Hilton
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ORD-SJO
Flights+Hotel
From
$826* Price subject to change
Viewed:a day ago
27/30
3Night(s) Trip
Hilton San Jose La Sabana
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ORD-SJO
Flights+Hotel
From
$889* Price subject to change
Viewed:a day ago
28/30
3Night(s) Trip
Hotel Presidente
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ORD-SJO
Flights+Hotel
From
$903* Price subject to change
Viewed:a day ago
29/30
3Night(s) Trip
InterContinental Costa Rica at Multiplaza Mall By IHG
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ORD-SJO
Flights+Hotel
From
$928* Price subject to change
Viewed:a day ago
30/30
3Night(s) Trip
Costa Rica Marriott Hotel Hacienda Belen
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ORD-SJO
Flights+Hotel
From
$977* Price subject to change
Viewed:a day ago
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*Average total price per person based on round trip flights and double occupancy hotel stays. Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply.
Current Weather in San Jose, CR
Tuesdaymoderate rain
76°F06/24/25
Wednesdayheavy intensity rain
76°F06/25/25
Thursdayvery heavy rain
76°F06/26/25
Fridaymoderate rain
72°F06/27/25
Saturdaymoderate rain
72°F06/28/25
Sundaymoderate rain
74°F06/29/25
Mondaymoderate rain
74°F06/30/25
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