Vacations from Chicago to Puerto Rico
Check Out Our Flight and Hotel Packages to Rome From - To
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cmp-carousel-container-explain 7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,228 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,242 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,246 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,269 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,297 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,300 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,315 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,379 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,387 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,390 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,540 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,576 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,580 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,580 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,680 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,712 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,714 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $1,888 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $2,039 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $2,087 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $2,116 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 hours ago
7 night(s)
Chicago (ORD) To San Juan (SJU)
6/15/2025 June 15, 2025
- 6/22/2025 June 22, 2025
Flight + Hotel
from $2,373 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
Updated: 16 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.