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Flights from Chicago Midway Airport to Hawaii

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Flight deals from Chicago Midway Airport to Hawaii

Looking for cheap tickets from Chicago Midway Airport to Hawaii, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.
Honolulu.£356 per passenger.Departing Wed, 10 Sep, returning Wed, 17 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 10 Sep, arriving in Honolulu International.Inbound indirect flight with Delta, departs from Honolulu International on Wed, 17 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £356, select.
Lihue.£401 per passenger.Departing Tue, 19 Aug, returning Tue, 26 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 19 Aug, arriving in Lihue.Inbound indirect flight with Southwest Airlines, departs from Lihue on Tue, 26 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £401, select.
Kahului.£426 per passenger.Departing Wed, 3 Sep, returning Tue, 9 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 3 Sep, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Tue, 9 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £426, select.
Kailua-Kona.£461 per passenger.Departing Tue, 6 May, returning Tue, 20 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 6 May, arriving in Kona.Inbound indirect flight with Delta, departs from Kona on Tue, 20 May, arriving in Chicago Midway.Price includes taxes and charges.From £461, select.
Hilo.£525 per passenger.Departing Mon, 12 May, returning Thu, 15 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 12 May, arriving in Hilo.Inbound indirect flight with Southwest Airlines, departs from Hilo on Thu, 15 May, arriving in Chicago Midway.Price includes taxes and charges.From £525, select.

Flying from Chicago Midway Airport to Hawaii

Arm yourself with these facts on the fly.
Cheapest flight found£356, Honolulu
Cheapest month to flySeptember

Frequently asked questions

There are currently no direct flights from Chicago Midway Airport to Hawaii, but we've found some other routes to United States – check them out now.
Chicago O'Hare International Airport offers direct flights to Hawaii.
We looked at all of the upcoming return flights from Chicago Midway Airport to Hawaii we could find over the next 12 months. It looks like £356 is the best price. This is good, compared to the average Hawaii ticket price of £623.
The cheapest month to fly from Chicago Midway Airport to Lihue Airport is currently August.
The cheapest month to fly from Chicago Midway Airport to Hilo Airport is currently May.
The cheapest month to fly from Chicago Midway Airport to Kona Airport is currently May.
And the cheapest month to fly from Chicago Midway Airport to Maui Kahului Airport is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago Midway Airport to Hawaii on Wednesday, 10 September 2025.
If you're flying from Chicago Midway, the cheapest city in Hawaii to fly into is Honolulu. The cheapest airport serving Honolulu at the moment is Honolulu International.