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Cheap Flights from Chicago to Kīhei

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      Travellers and cabin class, 1 Adult, Economy

      Compare Chicago to Kīhei flight deals

      Find the cheapest month or even day of the year to fly to Kīhei

      Book the best Kīhei fare with no extra fees

      Flight deals from Chicago to Kīhei

      Looking for a cheap last-minute deal or the best return flight from Chicago to Kīhei? Find the lowest prices on one-way and return tickets right here.
      Kahului.ر.ق.‏ 868 per passenger.Departing Wed, 9 Sep.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Wed, 9 Sep, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 868, select.
      Kahului.ر.ق.‏ 879 per passenger.Departing Tue, 25 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 25 Aug, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 879, select.
      Kahului.ر.ق.‏ 881 per passenger.Departing Tue, 6 Oct.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Tue, 6 Oct, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 881, select.
      Kahului.ر.ق.‏ 1,010 per passenger.Departing Tue, 1 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,010, select.
      Kahului.ر.ق.‏ 1,029 per passenger.Departing Sun, 1 Nov.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 1 Nov, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,029, select.
      Kahului.ر.ق.‏ 1,338 per passenger.Departing Sun, 3 Jan.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 3 Jan, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,338, select.
      Kahului.ر.ق.‏ 1,404 per passenger.Departing Fri, 31 Jul.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Fri, 31 Jul, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,404, select.
      Kahului.ر.ق.‏ 1,675 per passenger.Departing Mon, 15 Feb.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago O'Hare International on Mon, 15 Feb, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,675, select.
      Kahului.ر.ق.‏ 1,696 per passenger.Departing Sat, 17 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 17 Apr, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,696, select.
      Kahului.ر.ق.‏ 1,785 per passenger.Departing Sat, 1 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 1 May, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,785, select.
      Kahului.ر.ق.‏ 1,846 per passenger.Departing Mon, 18 Jan.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 18 Jan, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,846, select.
      Kahului.ر.ق.‏ 1,846 per passenger.Departing Mon, 15 Feb.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 15 Feb, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,846, select.
      Kahului.ر.ق.‏ 1,847 per passenger.Departing Tue, 2 Mar.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 2 Mar, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,847, select.
      Kahului.ر.ق.‏ 1,851 per passenger.Departing Thu, 31 Dec.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 31 Dec, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,851, select.
      Kahului.ر.ق.‏ 1,887 per passenger.Departing Sat, 1 May.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 1 May, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,887, select.
      Kahului.ر.ق.‏ 1,888 per passenger.Departing Sat, 31 Oct.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 31 Oct, arriving in Maui Kahului.Price includes taxes and charges.From ر.ق.‏ 1,888, select.
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      Chicago to Kīhei: Flight information

      The things to know before you go.
      Fly intoMaui Kahului Airport
      Distance to Kīhei15.8 km
      Cheapest flightر.ق.‏ 868
      Cheapest month to flySeptember
      Most popular airlineAmerican Airlines
      Average flight time9 hrs, 27 mins

      Find the cheapest month to fly from Chicago to Kīhei

      We always keep an eye on fares, so you can find the best flight deal in seconds. It looks like Chicago to Kīhei flights are currently cheapest in October. We’ve based this on flights into Maui Kahului Airport.
      Jul
      from ر.ق.‏ 1,404
      Aug
      from ر.ق.‏ 879
      Sep
      from ر.ق.‏ 868
      Oct
      from ر.ق.‏ 881
      Nov
      from ر.ق.‏ 1,029
      Dec
      from ر.ق.‏ 1,010
      Jan
      from ر.ق.‏ 1,338
      Feb
      from ر.ق.‏ 1,675
      Mar
      from ر.ق.‏ 1,847
      Apr
      from ر.ق.‏ 1,696
      May
      from ر.ق.‏ 1,785
      Jun
      from ر.ق.‏ 1,993

      Finding cheap flights from Chicago to Kīhei: Frequently asked questions

      There are 3 airports near Kīhei: Maui Kahului Airport, Kapalua Airport and Hana Airport.
      The best price we found for a return flight from Chicago to Kīhei is ر.ق.‏ 1,891. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      American Airlines and United both offer direct flights to Maui Kahului Airport.
      We've checked every Chicago to Kīhei fare we could find, and the cheapest upcoming date to fly seems to be on Tuesday, 20 October 2026. Overall, the cheapest month to fly from Chicago to Kīhei is usually October.
      If you're flying from Chicago, the cheapest airport near Kīhei is Maui Kahului – which is 15.8 km away from the centre of Kīhei. We've found flights into this airport from ر.ق.‏ 1,891.
      After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Kīhei on Tuesday, 20 October 2026.
      No airlines currently offer direct flights between Chicago and Kīhei. Most routes have one or more stops.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Kīhei but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Kīhei is around 40 days in advance, so don’t leave your flight to the last minute.

      Maui Kahului Airport is 15.8km from Kīhei, Kapalua Airport is 32.2km from Kīhei, and Hana Airport is 45.8km from Kīhei.
      Maui Kahului Airport is closest to Kīhei, at around 15.8 km away.
      The cheapest airline that flies to Kīhei is Alaska Airlines. And the cheapest airline that flies to Kapalua Airport is United.