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.

Kailua-Kona.Rs52,011 per passenger.Departing Sun, 18 Jan.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 18 Jan, arriving in Kona.Price includes taxes and charges.From Rs52,011, select.

Kahului.Rs54,245 per passenger.Departing Mon, 16 Feb.One-way flight with Hawaiian Airlines.Outbound indirect flight with Hawaiian Airlines, departs from Chicago O'Hare International on Mon, 16 Feb, arriving in Maui Kahului.Price includes taxes and charges.From Rs54,245, select.

Honolulu.Rs56,071 per passenger.Departing Mon, 8 Dec.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 8 Dec, arriving in Honolulu International.Price includes taxes and charges.From Rs56,071, select.

Lihue.Rs61,907 per passenger.Departing Sat, 26 Sep.One-way flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sat, 26 Sep, arriving in Lihue.Price includes taxes and charges.From Rs61,907, select.

Hilo.Rs115,757 per passenger.Departing Mon, 3 Nov.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Mon, 3 Nov, arriving in Hilo.Price includes taxes and charges.From Rs115,757, select.

Kapalua.Rs158,541 per passenger.Departing Sun, 28 Dec.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 28 Dec, arriving in Kapalua.Price includes taxes and charges.From Rs158,541, select.

Kamuela.Rs196,738 per passenger.Departing Fri, 26 Dec.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Fri, 26 Dec, arriving in Kamuela.Price includes taxes and charges.From Rs196,738, select.

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Flying from Chicago to Hawaii

Arm yourself with these facts on the fly.

Cheapest flight found	Rs52,011
Cheapest month to fly	January
Average flight time	9 hrs, 15 mins
Cheapest airport to fly from	Chicago Midway
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 Rs104,358 and one-way tickets from Rs52,011 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 December

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

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 Rs104,358 is the best price. This is good, compared to the average Hawaii ticket price of Rs139,130.

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

The cheapest month to fly from Chicago to Kona Airport is usually January. The cheapest month to fly from Chicago to Kapalua Airport is usually November. The cheapest month to fly from Chicago to Hilo Airport is usually December. And the cheapest month to fly from Chicago to Honolulu International Airport is usually December.

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 Thursday, 4 December 2025.

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.