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Cheap flights from Chicago to Kapalua from $1,046

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Kapalua departing on 9/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Kapalua

Cheap round-trip flights

Logo
3:20 pm - 1:50 pmORD-JHM
27h 30m2 stops
Logo
2:10 pm - 1:11 pmJHM-ORD
18h 01m2 stops
$1,046
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Thu, Sep 11 - Thu, Sep 18
Logo
5:10 pm - 1:50 pmORD-JHM
24h 40m3 stops
Logo
2:10 pm - 1:04 pmJHM-ORD
18h 54m2 stops
$1,115
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Sat, Dec 6 - Sat, Dec 13
Logo
2:07 pm - 1:50 pmORD-JHM
28h 43m2 stops
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2:10 pm - 1:11 pmJHM-ORD
18h 01m2 stops
$1,384
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Thu, Sep 11 - Thu, Sep 18

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Kapalua that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 30, 2025.
Use the filters below to find and compare flights from Chicago to Kapalua that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Thu 9/11

3:20 pm-1:50 pm

2 stops27h 30m

Kapalua West Maui

Thu 9/18

2:10 pm-1:11 pm

2 stops18h 01m

$1,046

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Sat 12/6

5:10 pm-1:50 pm

3 stops24h 40m

Kapalua West Maui

Sat 12/13

2:10 pm-1:04 pm

2 stops18h 54m

$1,115

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Thu 9/11

2:07 pm-1:50 pm

2 stops28h 43m

Kapalua West Maui

Thu 9/18

2:10 pm-1:11 pm

2 stops18h 01m

$1,384

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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How to get the cheapest flight ticket from Chicago to Kapalua

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What airlines fly to Kapalua?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Kapalua from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Kapalua. Keep in mind that there are 6 different airlines that fly to Kapalua on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago to Kapalua

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Kapalua according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Kapalua (CHI to JHM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Kapalua

Best Price Found

$1,046

Fastest flight time

24h 40m

Direct flights

None

Airports in Kapalua

1 airport
The best flight deal from Chicago to Kapalua found on momondo in the last 72 hours is $1,046
The fastest flight from Chicago to Kapalua takes 24h 40m
There are no direct flights from Chicago to Kapalua. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Kapalua West Maui Airport.
There is 1 airport near Kapalua: Kapalua West Maui (JHM)
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  • How far is Chicago to Kapalua West Maui by plane?

    The distance between Chicago and Kapalua West Maui is about 4197.4 mi. In terms of flight time, this usually takes a little over 24h 40m.

  • When did momondo last update prices for flights from Chicago to Kapalua West Maui Airport?

    Prices for flights from Chicago to Kapalua West Maui Airport are updated daily.

  • How old do you have to be to fly from Chicago to Kapalua West Maui Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Kapalua West Maui Airport.

  • What documentation or ID do you need to fly to Kapalua West Maui Airport?

    The necessary travel and health documents for your Kapalua West Maui Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Kapalua?

Book flights to Kapalua if you plan to visit one of these locations
Lahaina
Kaanapali

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kapalua?

It is quick and easy to find Chicago to Kapalua flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Kapalua that suits you.

Can I find flights from Chicago to Kapalua with flexible booking policies on momondo?

momondo does allow users to show only those flights to Kapalua from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Kapalua?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Kapalua from Chicago.

I’m not ready to book a flight from Chicago to Kapalua right now. Can momondo alert me if prices change?

Price alerts on flights to Kapalua from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Kapalua trip

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