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Cheap Flights from Chicago to Lahaina

Compare Chicago to Lahaina flight deals

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

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Flight deals from Chicago to Lahaina

Looking for a cheap last-minute deal or the best return flight from Chicago to Lahaina? Find the lowest prices on one-way and return tickets right here.
Kapalua.743 € per passenger.Departing Mon, 23 Feb, returning Thu, 5 Mar.Return flight with Frontier Airlines and Southern Airways Express.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 23 Feb, arriving in Kapalua.Inbound indirect flight with Southern Airways Express, departs from Kapalua on Thu, 5 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From 743 €, select.
Kapalua.788 € per passenger.Departing Mon, 2 Mar, returning Fri, 6 Mar.Return flight with Frontier Airlines and Southern Airways Express.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 2 Mar, arriving in Kapalua.Inbound indirect flight with Southern Airways Express, departs from Kapalua on Fri, 6 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From 788 €, select.
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Chicago to Lahaina: Flight information

The things to know before you go.
Fly intoKapalua Airport
Distance to Lahaina9.6 km
Cheapest flight743 €
Cheapest month to flyFebruary

Find the cheapest month to fly from Chicago to Lahaina

We always keep an eye on fares, so you can find the best flight deal in seconds. It looks like Chicago to Lahaina flights are currently cheapest in February. We’ve based this on flights into Kapalua Airport.
Feb
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Mar
from 788 €
Apr
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May
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Jul
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Aug
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Jan
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Finding cheap flights from Chicago to Lahaina: Frequently asked questions

There are 3 airports near Lahaina: Kapalua Airport, Maui Kahului Airport and Lanai City Airport.
The best price we found for a return flight from Chicago to Lahaina is 743 €. 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.
Currently, there are no airlines that fly direct from Chicago to Lahaina. But we found flights with one or more stops from 743 €.
We've checked every Chicago to Lahaina fare we could find, and the cheapest upcoming date to fly seems to be on Monday, 23 February 2026. Overall, the cheapest month to fly from Chicago to Lahaina is usually February.
If you're flying from Chicago, the cheapest airport near Lahaina is Kapalua – which is 9.6 km away from the centre of Lahaina. We've found flights into this airport from 743 €.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Lahaina on Monday, 23 February 2026.
No airlines currently offer direct flights between Chicago and Lahaina. 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 Lahaina 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 Lahaina is around 40 days in advance, so don’t leave your flight to the last minute.
Kapalua Airport is 9.6km from Lahaina, Maui Kahului Airport is 26.0km from Lahaina, and Lanai City Airport is 29.6km from Lahaina.
Kapalua Airport is closest to Lahaina, at around 9.6 km away.
The cheapest airline that flies to Lahaina is Frontier Airlines .