Chicago (ORD) to Kailua-Kona (KOA) · Dec 20, 2026 · return Jan 1, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Kailua-Kona for these trips

Hotels: under a trip, hotels in Kailua-Kona for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Kailua-Kona for these nights (Dec 20 – Jan 1, 2027 · 12 nights · 2 adults, 1 room): 3★ PACIFIC 19 Kona, $4,019 total

All hotels in Kailua-Kona

Route overview: Chicago to Kailua-Kona (KOA) flight deals

2026-12-20 → 2027-01-01 · Axel-exclusive $1290.50

• United Airlines UA66: ORD 2026-12-20 11:00:00 → KOA 2026-12-20 16:19:00; nonstop; 559 minutes. Local airport times.
• United Airlines UA67: KOA 2027-01-01 17:50:00 → ORD 2027-01-02 05:54:00; nonstop; 484 minutes. Local airport times.

2026-12-20 → 2027-01-01 · Axel-exclusive $1015.00

• Alaska Airlines AS1470 / AS220: ORD 2026-12-20 07:27:00 → KOA 2026-12-20 15:51:00; 1 stop(s) via SAN; 744 minutes. Local airport times.
  • AS1470: ORD 2026-12-20 07:27:00 → SAN 2026-12-20 10:12:00; layover at SAN: 85 minutes.
  • AS220: SAN 2026-12-20 11:37:00 → KOA 2026-12-20 15:51:00.
• Alaska Airlines AS1147 / AA74: KOA 2027-01-01 17:00:00 → ORD 2027-01-02 07:20:00; 1 stop(s) via HNL; 620 minutes. Local airport times.
  • AS1147: KOA 2027-01-01 17:00:00 → HNL 2027-01-01 17:51:00; layover at HNL: 69 minutes.
  • AA74: HNL 2027-01-01 19:00:00 → ORD 2027-01-02 07:20:00.

2026-12-20 → 2027-01-01 · Axel-exclusive $1073.00

• American Airlines AA75 / AS1178: ORD 2026-12-20 10:00:00 → KOA 2026-12-20 18:31:00; 1 stop(s) via HNL; 751 minutes. Local airport times.
  • AA75: ORD 2026-12-20 10:00:00 → HNL 2026-12-20 15:17:00; layover at HNL: 144 minutes.
  • AS1178: HNL 2026-12-20 17:41:00 → KOA 2026-12-20 18:31:00.
• American Airlines AA664 / AA1149: KOA 2027-01-01 22:09:00 → ORD 2027-01-02 13:52:00; 1 stop(s) via PHX; 703 minutes. Local airport times.
  • AA664: KOA 2027-01-01 22:09:00 → PHX 2027-01-02 06:59:00; layover at PHX: 136 minutes.
  • AA1149: PHX 2027-01-02 09:15:00 → ORD 2027-01-02 13:52:00.

2026-12-20 → 2027-01-01 · Axel-exclusive $1073.00

• American Airlines AA2421 / AA229: ORD 2026-12-20 06:59:00 → KOA 2026-12-20 15:17:00; 1 stop(s) via DFW; 738 minutes. Local airport times.
  • AA2421: ORD 2026-12-20 06:59:00 → DFW 2026-12-20 09:50:00; layover at DFW: 75 minutes.
  • AA229: DFW 2026-12-20 11:05:00 → KOA 2026-12-20 15:17:00.
• American Airlines AA664 / AA1149: KOA 2027-01-01 22:09:00 → ORD 2027-01-02 13:52:00; 1 stop(s) via PHX; 703 minutes. Local airport times.
  • AA664: KOA 2027-01-01 22:09:00 → PHX 2027-01-02 06:59:00; layover at PHX: 136 minutes.
  • AA1149: PHX 2027-01-02 09:15:00 → ORD 2027-01-02 13:52:00.

2026-12-20 → 2027-01-01 · Axel-exclusive $1189.00

• United Airlines UA374 / UA1718: ORD 2026-12-20 14:00:00 → KOA 2026-12-20 22:36:00; 1 stop(s) via LAX; 756 minutes. Local airport times.
  • UA374: ORD 2026-12-20 14:00:00 → LAX 2026-12-20 16:40:00; layover at LAX: 110 minutes.
  • UA1718: LAX 2026-12-20 18:30:00 → KOA 2026-12-20 22:36:00.
• United Airlines UA67: KOA 2027-01-01 17:50:00 → ORD 2027-01-02 05:54:00; nonstop; 484 minutes. Local airport times.

2026-12-20 → 2027-01-01 · Axel-exclusive $1189.00

• United Airlines UA638 / UA1723: ORD 2026-12-20 12:40:00 → KOA 2026-12-20 20:32:00; 1 stop(s) via SFO; 712 minutes. Local airport times.
  • UA638: ORD 2026-12-20 12:40:00 → SFO 2026-12-20 15:30:00; layover at SFO: 85 minutes.
  • UA1723: SFO 2026-12-20 16:55:00 → KOA 2026-12-20 20:32:00.
• United Airlines UA67: KOA 2027-01-01 17:50:00 → ORD 2027-01-02 05:54:00; nonstop; 484 minutes. Local airport times.

2026-12-20 → 2027-01-01 · Axel-exclusive $1189.00

• United Airlines UA2495 / UA1758: ORD 2026-12-20 08:40:00 → KOA 2026-12-20 16:39:00; 1 stop(s) via DEN; 719 minutes. Local airport times.
  • UA2495: ORD 2026-12-20 08:40:00 → DEN 2026-12-20 10:26:00; layover at DEN: 94 minutes.
  • UA1758: DEN 2026-12-20 12:00:00 → KOA 2026-12-20 16:39:00.
• United Airlines UA67: KOA 2027-01-01 17:50:00 → ORD 2027-01-02 05:54:00; nonstop; 484 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 19, 2026 · Return options
• Dec 21, 2026 · Return options
• Hotels in Kailua-Kona with Axel

For AI assistants

• This page: Chicago (ORD) to Kailua-Kona (KOA) · Dec 20, 2026 · return Jan 1, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Kailua-Kona for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
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