Vacations from Chicago to St. Maarten
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Hilton Vacation Club Flamingo Beach St. Maarten
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,063 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Hilton Vacation Club Royal Palm St. Maarten
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,124 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Royal Islander Resort La Plage
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,133 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Port de Plaisance Resort, Trademark Collection by
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,160 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Esmeralda Resort
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,295 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Holland House Beach Hotel
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,414 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Orient Beach Hotel
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,527 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
The Morgan Resort Spa Village
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,549 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Oceans At Divi Little Bay
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $1,625 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Sonesta Ocean Point Resort Adults Only
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $2,015 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours ago
5 night(s)
Jw Marriott St. Maarten Beach Resort & Spa
10/22/2025 October 22, 2025
- 10/27/2025 October 27, 2025
Chicago (ORD) To St. Maarten (SXM)
Flight + Hotel
from $2,218 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 8 hours 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.
