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Cheap flights from Chicago to Kapalua from $469

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Kapalua departing on 3/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Kapalua

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:06 pm - 1:50 pm
ORD
-
JHM
23h 44m3 stops
Multiple Airlines Logo
2:10 pm - 5:10 pm
JHM
-
ORD
23h 00m2 stops
$822Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
6:06 pm - 1:50 pm
ORD
-
JHM
23h 44m3 stops
Multiple Airlines Logo
2:10 pm - 1:10 pm
JHM
-
ORD
19h 00m2 stops
$964Multiple Airlines
Fri, Jan 30 - Thu, Feb 5
Multiple Airlines Logo
5:29 pm - 1:50 pm
ORD
-
JHM
24h 21m3 stops
Multiple Airlines Logo
2:10 pm - 2:11 pm
JHM
-
ORD
20h 01m2 stops
$1,053Multiple Airlines
Mon, Feb 16 - Sun, Mar 1
Multiple Airlines Logo
6:50 pm - 1:50 pm
ORD
-
JHM
24h 00m3 stops
Multiple Airlines Logo
2:10 pm - 2:21 pm
JHM
-
ORD
19h 11m2 stops
$1,098Multiple Airlines
Mon, Mar 23 - Mon, Mar 30
Multiple Airlines Logo
6:08 pm - 1:50 pm
ORD
-
JHM
23h 42m3 stops
Multiple Airlines Logo
2:10 pm - 1:10 pm
JHM
-
ORD
19h 00m2 stops
$1,521Multiple Airlines
Thu, Jan 1 - Thu, Jan 8

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 December 4, 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

Tue 2/3

6:06 pm-1:50 pm

3 stops23h 44m

Kapalua West Maui

Tue 2/10

2:10 pm-5:10 pm

2 stops23h 00m

$822

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Fri 1/30

6:06 pm-1:50 pm

3 stops23h 44m

Kapalua West Maui

Thu 2/5

2:10 pm-1:10 pm

2 stops19h 00m

$964

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Mon 2/16

5:29 pm-1:50 pm

3 stops24h 21m

Kapalua West Maui

Sun 3/1

2:10 pm-2:11 pm

2 stops20h 01m

$1,053

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Mon 3/23

6:50 pm-1:50 pm

3 stops24h 00m

Kapalua West Maui

Mon 3/30

2:10 pm-2:21 pm

2 stops19h 11m

$1,098

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Thu 1/1

6:08 pm-1:50 pm

3 stops23h 42m

Kapalua West Maui

Thu 1/8

2:10 pm-1:10 pm

2 stops19h 00m

$1,521

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Sun 3/29

9:38 pm-1:50 pm

2 stops45h 12m

$469

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Sun 3/29

9:38 pm-1:50 pm

3 stops45h 12m

$476

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Kapalua from

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 41% 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

Fastest flight time

23h 42m

Direct flights

None
The fastest flight from Chicago to Kapalua takes 23h 42m
There are no direct flights from Chicago to Kapalua. There are no popular flight routes from Chicago to Kapalua.
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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 23h 42m.

  • 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.

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