Vacations from Chicago to Big Island Hawaii
See other vacation package offers From - To
From cmp-location-selector-label-description-origin
To cmp-location-selector-label-description-destination
Close
5-7 nights
Choose your night stays Any number of nights
Close
Clear
cmp-carousel-container-explain 7 night(s)
OUTRIGGER Kona Resort and Spa
7/07/2025 July 7, 2025
- 7/14/2025 July 14, 2025
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $1,851 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Hilton Waikoloa Village
7/07/2025 July 7, 2025
- 7/14/2025 July 14, 2025
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $2,234 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Waikoloa Beach Marriott Resort & Spa
7/07/2025 July 7, 2025
- 7/14/2025 July 14, 2025
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $2,496 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Fairmont Orchid - Hawaii
7/07/2025 July 7, 2025
- 7/14/2025 July 14, 2025
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $2,863 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Hilton Grand Vacations Club Kings’ Land Waikoloa
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $4,194 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
The Westin Hapuna Beach Resort
7/07/2025 July 7, 2025
- 7/14/2025 July 14, 2025
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $4,245 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Castle Halii Kai at Waikoloa
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $4,464 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
Four Seasons Resort Hualalai
7/07/2025 July 7, 2025
- 7/14/2025 July 14, 2025
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $6,065 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Mauna Lani, Auberge Resorts Collection
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $7,312 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
Mauna Kea Beach Hotel, Autograph Collection
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $8,972 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
Kona Village, A Rosewood Resort
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $9,241 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
OUTRIGGER Kona Resort and Spa
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $3,861 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
Waikoloa Beach Marriott Resort & Spa
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $5,268 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
Fairmont Orchid - Hawaii
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $5,931 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
7 night(s)
Four Seasons Resort Hualalai
1/17/2026 January 17, 2026
- 1/24/2026 January 24, 2026
Chicago (ORD) To Big Island Hawaii (KOA)
Flight + Hotel
from $11,516 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 10 hours ago
cmp-carousel-slide 1 cmp-carousel-of 4
*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.
Disclaimer
cmp-disclaimer-link3
cmp-disclaimer-link4
Discover our best deals from Chicago to Big Island Hawaii See the best deals from your origin.
*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.
Powered by: OpenWeatherMap.org