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Flights from Chicago to Hawaii

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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.
Lihue.R 7,528 per passenger.Departing Fri, 5 Sep, returning Mon, 15 Sep.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Fri, 5 Sep, arriving in Lihue.Inbound indirect flight with United, departs from Lihue on Mon, 15 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 7,528, select.
Honolulu.R 8,475 per passenger.Departing Sat, 1 Nov, returning Sat, 8 Nov.Return flight with Spirit Airlines and Hawaiian Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 1 Nov, arriving in Honolulu International.Inbound indirect flight with Hawaiian Airlines, departs from Honolulu International on Sat, 8 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 8,475, select.
Kailua-Kona.R 9,118 per passenger.Departing Mon, 10 Nov, returning Mon, 17 Nov.Return flight with Spirit Airlines and Alaska Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 10 Nov, arriving in Kona.Inbound indirect flight with Alaska Airlines, departs from Kona on Mon, 17 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 9,118, select.
Kahului.R 9,529 per passenger.Departing Tue, 11 Nov, returning Mon, 17 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 11 Nov, arriving in Maui Kahului.Inbound indirect flight with Delta, departs from Maui Kahului on Mon, 17 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 9,529, select.
Hilo.R 14,601 per passenger.Departing Thu, 10 Jul, returning Thu, 17 Jul.Return flight with Hawaiian Airlines.Outbound indirect flight with Hawaiian Airlines, departs from Chicago O'Hare International on Thu, 10 Jul, arriving in Hilo.Inbound indirect flight with Hawaiian Airlines, departs from Hilo on Thu, 17 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 14,601, select.

Flying from Chicago to Hawaii

Arm yourself with these facts on the fly.
Cheapest flight foundR 3,770, Lihue
Cheapest month to flyAugust
Average flight time9 hrs, 11 mins
Cheapest airport to fly fromChicago O'Hare International
Most popular airlineQantas

Frequently asked questions

We looked at all of the upcoming return flights from Chicago to Hawaii we could find over the next 12 months. It looks like R 7,528 is the best price. This is good, compared to the average Hawaii ticket price of R 14,496.
The cheapest month to fly from Chicago to Lihue Airport is usually September. The cheapest month to fly from Chicago to Kona Airport is usually November. The cheapest month to fly from Chicago to Hilo Airport is usually July. And the cheapest month to fly from Chicago to Maui Kahului Airport is usually November.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Hawaii on Friday, 5 September 2025.
Chicago O'Hare International Airport offers direct flights to Hawaii.
If you're flying from Chicago, the cheapest city in Hawaii to fly into is Lihue. The cheapest airport serving Lihue at the moment is Lihue.
The average flight time between Chicago and Hawaii is 9 hours and 11 minutes.