Skyscanner home

Flight tickets from Chicago to Kīhei

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.₹ 20,729 per passenger.Departing Mon, 31 Aug.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 31 Aug, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 20,729, select.
Kahului.₹ 26,235 per passenger.Departing Tue, 1 Sep.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 1 Sep, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 26,235, select.
Kahului.₹ 27,059 per passenger.Departing Sun, 15 Nov.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sun, 15 Nov, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 27,059, select.
Kahului.₹ 31,267 per passenger.Departing Tue, 13 Oct.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 13 Oct, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 31,267, select.
Kahului.₹ 33,628 per passenger.Departing Thu, 9 Jul.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Thu, 9 Jul, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 33,628, select.
Kahului.₹ 34,988 per passenger.Departing Thu, 25 Jun.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 25 Jun, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 34,988, select.
Kahului.₹ 35,183 per passenger.Departing Mon, 4 Jan.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 4 Jan, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 35,183, select.
Kahului.₹ 46,983 per passenger.Departing Mon, 12 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 12 Apr, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 46,983, select.
Kahului.₹ 47,003 per passenger.Departing Mon, 15 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 15 Feb, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 47,003, select.
Kahului.₹ 49,013 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 ₹ 49,013, select.
Kahului.₹ 49,423 per passenger.Departing Thu, 4 Mar.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 4 Mar, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 49,423, select.
Kahului.₹ 49,939 per passenger.Departing Sat, 9 Jan.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 9 Jan, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 49,939, select.
Kahului.₹ 50,172 per passenger.Departing Sat, 10 Apr.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 10 Apr, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 50,172, select.
Kahului.₹ 50,199 per passenger.Departing Tue, 1 Dec.One-way flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 50,199, select.
Kahului.₹ 50,218 per passenger.Departing Sat, 24 Oct.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 50,218, select.
Kahului.₹ 50,218 per passenger.Departing Sat, 5 Dec.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 5 Dec, arriving in Maui Kahului.Price includes taxes and charges.From ₹ 50,218, select.
Show more deals

Chicago to Kīhei: Flight information

The things to know before you go.
Fly intoMaui Kahului Airport
Distance to Kīhei15.9 km
Cheapest flight₹ 20,729
Cheapest month to flyAugust
Most popular airlineAmerican Airlines
Average flight time9 hrs, 25 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 September. We’ve based this on flights into Maui Kahului Airport.
Jun
from ₹ 34,988
Jul
from ₹ 33,628
Aug
from ₹ 20,729
Sep
from ₹ 26,235
Oct
from ₹ 31,267
Nov
from ₹ 27,059
Dec
from ₹ 50,199
Jan
from ₹ 35,183
Feb
from ₹ 47,003
Mar
from ₹ 49,423
Apr
from ₹ 46,983
May
Find prices

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 ₹ 52,415. 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, 1 September 2026. Overall, the cheapest month to fly from Chicago to Kīhei is usually September.
If you're flying from Chicago, the cheapest airport near Kīhei is Maui Kahului – which is 15.9 km away from the centre of Kīhei. We've found flights into this airport from ₹ 52,415.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Kīhei on Tuesday, 1 September 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 15.9km from Kīhei, Kapalua Airport is 32.3km from Kīhei, and Hana Airport is 45.8km from Kīhei.
Maui Kahului Airport is closest to Kīhei, at around 15.9 km away.
The cheapest airline that flies to Kīhei is Delta. And the cheapest airline that flies to Kapalua Airport is United.