Vacations from Chicago to Oahu
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cmp-carousel-container-explain 6 night(s)
Romer House Waikiki
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,338 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
OUTRIGGER Waikiki Paradise Hotel
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,464 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Alohilani Resort Waikiki Beach
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,584 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
OUTRIGGER Waikiki Beachcomber Hotel
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,651 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Hotel Renew
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,681 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Prince Waikiki
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,764 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Hilton Hawaiian Village Waikiki Beach Resort
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,798 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
OUTRIGGER Reef Waikiki Beach Resort
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,799 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Queen Kapiolani Hotel
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $1,818 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
OUTRIGGER Waikiki Beach Resort
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $2,018 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Waikiki Shore by OUTRIGGER
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $2,116 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Hyatt Regency Waikiki Beach Resort and Spa
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $2,159 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Waikiki Beach Marriott Resort & Spa
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $2,212 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Moana Surfrider, A Westin Resort & Spa, Waikiki Beach
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $2,302 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
6 night(s)
Four Seasons Resort Oahu at Ko Olina
5/03/2026 May 3, 2026
- 5/09/2026 May 9, 2026
Chicago (ORD) To Oahu (HNL)
Flight + Hotel
from $3,817 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 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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