Vacations from Chicago to Maui
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Lumeria Maui Educational Retreat Center
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,590 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
5 night(s)
AEI at Kaanapali Shores
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,624 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
5 night(s)
AEI at The Mahana Kaanapali Resort
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,655 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
5 night(s)
The Kapalua Villas Maui
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,681 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
5 night(s)
OUTRIGGER Honua Kai Resort and Spa
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,786 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
5 night(s)
The Westin Maui Resort & Spa, Ka'anapali
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,828 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
5 night(s)
Sheraton Maui Resort & Spa
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,854 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 16 hours ago
5 night(s)
The Ritz-Carlton Maui, Kapalua
1/07/2026 January 7, 2026
- 1/12/2026 January 12, 2026
Chicago (ORD) To Maui (OGG)
Flight + Hotel
from $1,954 * cmp-price-disclaimer
Per person based on 2-person occupancy 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.
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