Cheap flights from Chicago to Kailua-Kona

Compare flight prices from Chicago to Kailua-Kona across airlines and travel sites, see the cheapest month and day to fly, then book direct with the seller.

Lowest fare$275
Cheapest monthDecember 2026
Typical flight time10h 44m
Direct flightsNo

Lowest fare by month

–November 2026
$275December 2026
–January 2027
–February 2027
–March 2027
–April 2027

Airlines on this route

Frequently asked questions

What is the cheapest month to fly from Chicago to Kailua-Kona?

December 2026 has had the lowest recent fares, from $275 one way.

How long is the flight from Chicago to Kailua-Kona?

A typical flight takes about 10h 44m.

Are there direct flights from Chicago to Kailua-Kona?

No direct flights were found recently. Most trips include a stop.

Where do I book my ticket?

AirTriply compares fares from airlines and travel agencies. When you choose a deal, you book on the seller's own website.

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