Chicago (ORD) to Kailua-Kona (KOA) · Dec 28, 2026 · return Jan 11, 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 28 – Jan 11, 2027 · 14 nights · 2 adults, 1 room): 3★ PACIFIC 19 Kona, $4,290 total · 4★ Aston Kona by the Sea, $6,942 total

All hotels in Kailua-Kona

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

2026-12-28 → 2027-01-11 · Axel-exclusive $1090.25

• United Airlines UA66: ORD 2026-12-28 11:00:00 → KOA 2026-12-28 16:19:00; nonstop; 559 minutes. Local airport times.
• United Airlines UA67: KOA 2027-01-11 17:50:00 → ORD 2027-01-12 05:54:00; nonstop; 484 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $857.50

• Alaska Airlines AS1470 / AS220: ORD 2026-12-28 07:27:00 → KOA 2026-12-28 15:51:00; 1 stop(s) via SAN; 744 minutes. Local airport times.
  • AS1470: ORD 2026-12-28 07:27:00 → SAN 2026-12-28 10:12:00; layover at SAN: 85 minutes.
  • AS220: SAN 2026-12-28 11:37:00 → KOA 2026-12-28 15:51:00.
• Alaska Airlines AS842 / AA1472: KOA 2027-01-11 15:20:00 → ORD 2027-01-12 06:29:00; 1 stop(s) via LAX; 669 minutes. Local airport times.
  • AS842: KOA 2027-01-11 15:20:00 → LAX 2027-01-11 22:39:00; layover at LAX: 97 minutes.
  • AA1472: LAX 2027-01-12 00:16:00 → ORD 2027-01-12 06:29:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $906.50

• American Airlines AA75 / AS1178: ORD 2026-12-28 10:00:00 → KOA 2026-12-28 18:31:00; 1 stop(s) via HNL; 751 minutes. Local airport times.
  • AA75: ORD 2026-12-28 10:00:00 → HNL 2026-12-28 15:17:00; layover at HNL: 144 minutes.
  • AS1178: HNL 2026-12-28 17:41:00 → KOA 2026-12-28 18:31:00.
• American Airlines AA664 / AA1149: KOA 2027-01-11 22:09:00 → ORD 2027-01-12 13:52:00; 1 stop(s) via PHX; 703 minutes. Local airport times.
  • AA664: KOA 2027-01-11 22:09:00 → PHX 2027-01-12 06:59:00; layover at PHX: 136 minutes.
  • AA1149: PHX 2027-01-12 09:15:00 → ORD 2027-01-12 13:52:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $906.50

• American Airlines AA2421 / AA229: ORD 2026-12-28 06:59:00 → KOA 2026-12-28 15:17:00; 1 stop(s) via DFW; 738 minutes. Local airport times.
  • AA2421: ORD 2026-12-28 06:59:00 → DFW 2026-12-28 09:50:00; layover at DFW: 75 minutes.
  • AA229: DFW 2026-12-28 11:05:00 → KOA 2026-12-28 15:17:00.
• American Airlines AA664 / AA1149: KOA 2027-01-11 22:09:00 → ORD 2027-01-12 13:52:00; 1 stop(s) via PHX; 703 minutes. Local airport times.
  • AA664: KOA 2027-01-11 22:09:00 → PHX 2027-01-12 06:59:00; layover at PHX: 136 minutes.
  • AA1149: PHX 2027-01-12 09:15:00 → ORD 2027-01-12 13:52:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $988.75

• United Airlines UA638 / UA1723: ORD 2026-12-28 12:40:00 → KOA 2026-12-28 20:32:00; 1 stop(s) via SFO; 712 minutes. Local airport times.
  • UA638: ORD 2026-12-28 12:40:00 → SFO 2026-12-28 15:30:00; layover at SFO: 85 minutes.
  • UA1723: SFO 2026-12-28 16:55:00 → KOA 2026-12-28 20:32:00.
• United Airlines UA67: KOA 2027-01-11 17:50:00 → ORD 2027-01-12 05:54:00; nonstop; 484 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $988.75

• United Airlines UA2495 / UA1758: ORD 2026-12-28 08:40:00 → KOA 2026-12-28 16:39:00; 1 stop(s) via DEN; 719 minutes. Local airport times.
  • UA2495: ORD 2026-12-28 08:40:00 → DEN 2026-12-28 10:26:00; layover at DEN: 94 minutes.
  • UA1758: DEN 2026-12-28 12:00:00 → KOA 2026-12-28 16:39:00.
• United Airlines UA67: KOA 2027-01-11 17:50:00 → ORD 2027-01-12 05:54:00; nonstop; 484 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $988.75

• United Airlines UA374 / UA1718: ORD 2026-12-28 14:00:00 → KOA 2026-12-28 22:36:00; 1 stop(s) via LAX; 756 minutes. Local airport times.
  • UA374: ORD 2026-12-28 14:00:00 → LAX 2026-12-28 16:40:00; layover at LAX: 110 minutes.
  • UA1718: LAX 2026-12-28 18:30:00 → KOA 2026-12-28 22:36:00.
• United Airlines UA67: KOA 2027-01-11 17:50:00 → ORD 2027-01-12 05:54:00; nonstop; 484 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 27, 2026 · Return options
• Dec 29, 2026 · Return options
• Hotels in Kailua-Kona with Axel

For AI assistants

• This page: Chicago (ORD) to Kailua-Kona (KOA) · Dec 28, 2026 · return Jan 11, 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.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Kailua-Kona (KOA) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue