How to get from Chicago to Kailua-Kona: connecting flights, about 12h 50m total

Flights from Chicago to Kailua-Kona

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We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Best fares from Chicago to Kailua-Kona

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $374 4 December 2026, with a connection Cheapest weekend departure $374 Fri, 4 December 2026 Cheapest month December 2026 tickets from $374

Where to connect

Options with one connection, fastest first

fastest, via Kahului: 12h 50m
two tickets, via Los Angeles: $338
connection options: 5
straight-line distance: 4,222 mi (6,794 km)

fastest

Via Kahului

12h 50m

with the connection

Chicago to Kahului flight 9h 10m

Connection of about 3h

Kahului to Kailua-Kona flight 40m

Via Honolulu

13h 18m

with the connection

Chicago to Honolulu flight 9h 28m

Connection of about 3h

Honolulu to Kailua-Kona flight 50m

two ticketsfrom $436

Via Salt Lake City

13h 29m

with the connection

Chicago to Salt Lake City flight 3h 41m

Connection of about 3h

Salt Lake City to Kailua-Kona flight 6h 48m

Via Las Vegas

13h 30m

with the connection

Chicago to Las Vegas flight 4h 10m

Connection of about 3h

Las Vegas to Kailua-Kona flight 6h 20m

Via Los Angeles

13h 31m

with the connection

Chicago to Los Angeles flight 4h 41m

Connection of about 3h

Los Angeles to Kailua-Kona flight 5h 50m

two ticketsfrom $338

One ticket or two

How the options are calculated and what to keep in mind at the connection

Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.

Nearest nonstop flights

The closest you can get without a connection

From Chicago to cities closest to Kailua-Kona

Chicago to Kahului Kahului: 84 mi (135 km) from Kailua-Kona, flight 9h 10m from $393 Chicago to Honolulu Honolulu: 160 mi (258 km) from Kailua-Kona, flight 9h 28m from $258 Chicago to San Francisco San Francisco: 2,368 mi (3,811 km) from Kailua-Kona, flight 5h 6m from $140 Chicago to Sacramento Sacramento: 2,436 mi (3,920 km) from Kailua-Kona, flight 4h 40m from $217 Chicago to Santa Barbara Santa Barbara: 2,438 mi (3,923 km) from Kailua-Kona, flight 4h 53m Chicago to Fresno Fresno: 2,479 mi (3,989 km) from Kailua-Kona, flight 8h 54m

To Kailua-Kona from cities closest to Chicago

New York to Kailua-Kona New York: 711 mi (1,144 km) from Chicago, flight 15h 6m from $349 Denver to Kailua-Kona Denver: 918 mi (1,477 km) from Chicago, flight 7h 45m Salt Lake City to Kailua-Kona Salt Lake City: 1,257 mi (2,023 km) from Chicago, flight 6h 48m Phoenix to Kailua-Kona Phoenix: 1,452 mi (2,336 km) from Chicago, flight 6h 42m Las Vegas to Kailua-Kona Las Vegas: 1,521 mi (2,448 km) from Chicago, flight 6h 20m Los Angeles to Kailua-Kona Los Angeles: 1,742 mi (2,804 km) from Chicago, flight 5h 50m from $220

Frequently asked questions

Is there a nonstop flight from Chicago to Kailua-Kona?

There are no nonstop flights in the schedule. You will need a connection, the fastest is via Kahului.

What is the fastest way to fly from Chicago to Kailua-Kona?

Via Kahului: 9h 10m to the connection, 40m after it, about 12h 50m in total with 3h for the connection.

How much does a flight from Chicago to Kailua-Kona with a connection cost?

Two nonstop tickets via Los Angeles from $338. This is the sum of the lowest known prices for each leg, and their dates may not match.

Which cities can you connect in between Chicago and Kailua-Kona?

Kahului (12h 50m total), Honolulu (13h 18m total), Salt Lake City (13h 29m total), Las Vegas (13h 30m total) and Los Angeles (13h 31m total).

How far is Kailua-Kona from Chicago?

4,222 mi (6,794 km) in a straight line between the cities.

How much time should I allow for the connection?

The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.