Flights from Chicago to Hawaii

Flight deals from Chicago to Hawaii

Looking for cheap tickets from Chicago to Hawaii, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Kahului.SAR 1,406 per passenger.Departing Wed, 14 Jan, returning Wed, 21 Jan.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Wed, 14 Jan, arriving in Maui Kahului.Inbound indirect flight with Alaska Airlines, departs from Maui Kahului on Wed, 21 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 1,406, select.

Kailua-Kona.SAR 1,429 per passenger.Departing Sat, 25 Oct, returning Tue, 28 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 25 Oct, arriving in Kona.Inbound indirect flight with Delta, departs from Kona on Tue, 28 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 1,429, select.

Lihue.SAR 1,534 per passenger.Departing Tue, 21 Oct, returning Tue, 28 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 21 Oct, arriving in Lihue.Inbound indirect flight with Delta, departs from Lihue on Tue, 28 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 1,534, select.

Hilo.SAR 1,667 per passenger.Departing Thu, 4 Dec, returning Mon, 8 Dec.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Thu, 4 Dec, arriving in Hilo.Inbound indirect flight with Alaska Airlines, departs from Hilo on Mon, 8 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 1,667, select.

Honolulu.SAR 1,707 per passenger.Departing Tue, 6 Jan, returning Sun, 11 Jan.Return flight with Hawaiian Airlines.Outbound indirect flight with Hawaiian Airlines, departs from Chicago O'Hare International on Tue, 6 Jan, arriving in Honolulu International.Inbound indirect flight with Hawaiian Airlines, departs from Honolulu International on Sun, 11 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 1,707, select.

Lanai City.SAR 2,666 per passenger.Departing Sun, 9 Nov, returning Sat, 15 Nov.Return flight with Frontier Airlines and Southern Airways Express.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 9 Nov, arriving in Lanai City.Inbound indirect flight with Southern Airways Express, departs from Lanai City on Sat, 15 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,666, select.

Kapalua.SAR 2,857 per passenger.Departing Mon, 20 Oct, returning Mon, 27 Oct.Return flight with Frontier Airlines and Southern Airways Express.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 20 Oct, arriving in Kapalua.Inbound indirect flight with Southern Airways Express, departs from Kapalua on Mon, 27 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,857, select.

Hana.SAR 2,970 per passenger.Departing Sat, 25 Oct, returning Thu, 30 Oct.Return flight with Frontier Airlines and Southern Airways Express.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 25 Oct, arriving in Hana.Inbound indirect flight with Southern Airways Express, departs from Hana on Thu, 30 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 2,970, select.

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Flying from Chicago to Hawaii

Arm yourself with these facts on the fly.

Cheapest flight found	SAR 1,406
Cheapest month to fly	January
Average flight time	9 hrs, 14 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	Alaska Airlines

How to find cheap flights from Chicago to Hawaii

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Hawaii. Other savvy travellers recently found return flights from SAR 1,406 and one-way tickets from SAR 712 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Maui Kahului

At the moment, the lowest priced flight tickets to Hawaii are from Chicago O'Hare International Airport to Maui Kahului Airport.

Fly in January

We crunched the flight calendar and found the cheapest time to fly from Chicago to Hawaii is currently January.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Hawaii.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Hawaii go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Hawaii to Hawaii flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Hawaii flight price?

We looked at all of the upcoming return flights from Chicago to Hawaii we could find over the next 12 months. It looks like SAR 1,406 is the best price. This is good, compared to the average Hawaii ticket price of SAR 2,139.

What is the cheapest month to fly from Chicago to Hawaii?

The cheapest month to fly from Chicago to Lanai City Airport is usually November. The cheapest month to fly from Chicago to Hilo Airport is usually December. The cheapest month to fly from Chicago to Maui Kahului Airport is usually January. And the cheapest month to fly from Chicago to Kamuela Airport is usually October.

Which upcoming date is cheapest to fly from Chicago to Hawaii on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Hawaii on Wednesday, 14 January 2026.

Are there any direct flights from Chicago to Hawaii?

Chicago O'Hare International Airport offers direct flights to Hawaii.

If I'm flying from Chicago, where in Hawaii is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Hawaii to fly into is Kahului. The cheapest airport serving Kahului at the moment is Maui Kahului.