Vacations from Chicago to Maui
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The Kapalua Villas Maui
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $2,126 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Hana Maui Resort
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $2,631 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
OUTRIGGER Honua Kai Resort and Spa
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $2,642 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Hyatt Regency Maui Resort and Spa
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $2,924 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
The Westin Ka'Anapali Ocean Resort Villas
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $3,526 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Fairmont Kea Lani Maui
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $3,628 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Andaz Maui at Wailea Resort
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $3,683 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Wailea Beach Resort - Marriott, Maui
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $3,715 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Hotel Wailea, Relais & Chateaux - Adults Only
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $4,702 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Grand Wailea Maui, A Waldorf Astoria Resort
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $5,075 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Four Seasons Resort Maui at Wailea
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $5,663 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
7 night(s)
Wailea Beach Villas
10/09/2025 October 9, 2025
- 10/16/2025 October 16, 2025
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $6,255 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 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.
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