Cheap flights from Chicago (CHI) to Kapalua (OGG)

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Lowest round trip fares by airline from Chicago and Kapalua

Cheapest prices ($232 One Way, $414 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Kapalua

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive, Kapalua, HI
The price is $903 per night from Dec 1 to Dec 2
$903
includes taxes & fees
$774 per night
Dec 1 - Dec 2
Stay at this 5-star luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
9/10 Wonderful! (1,000 reviews)
"Had a wonderful stay for our anniversary and we definitely will be back! The service was impeccable and everyone was SO friendly wherever we went in the hotel, even the housekeeping when passing in the halls. It's so rare these days, even in top hotels. Breakfast was a little overpriced for the ala ..."

Reviewed on Nov 17, 2024

The Ritz-Carlton Maui, Kapalua
Napili Sunset on the Beach

Napili Sunset on the Beach

2.5 out of 5
46 Hui Drive, Lahaina, HI
The price is $269 per night from Nov 23 to Nov 24
$269
includes taxes & fees
$228 per night
Nov 23 - Nov 24
Book a stay at this beach aparthotel in Kapalua. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (600 reviews)
"Very Nice Soot! Cozy!"

Reviewed on Nov 18, 2024

Napili Sunset on the Beach
Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

3 out of 5
5315 Lower Honoapiilani Rd, Lahaina, HI
Stay at this 3-star beach aparthotel in Napili. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,531 reviews)
"Lovely peaceful place. Lots of grass for kids to play on. Pool was perfect temperature and the gentleman doing maintenance/cleaning was extremely through and very friendly."

Reviewed on Nov 17, 2024

Napili Shores Maui by OUTRIGGER
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Kapalua

Origin
Chicago
Destination
Kapalua
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Cheap flights from Chicago to Kapalua

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.

Save Even More Time and Money With a Kapalua Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Kapalua vacation that you can't get when you book flights and hotel separately.

Relax in Kapalua With Confidence and Convenience

Going cheap doesn't mean giving up great service. Our agents are available 24/7 to help you find the right cheap flights and hotel, and to answer questions about your trip.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.