Cheap flights from MDW to LUP (Midway Intl. to Kalaupapa)

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Hotel Ideas near Kalaupapa

Airport Hotels near Kalaupapa

Hotel Moloka'i

Hotel Moloka'i

3 out of 5
1300 Kamehameha V Hwy Kaunakakai HI
$224 nightly
The price is $266 total per night from Jun 13 to Jun 14
$266 total
Jun 13 - Jun 14
Total with taxes and fees
Book a stay at this beach hotel in Kaunakakai. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (679 reviews)
"This hotel is very charming and old-fashioned in the best way. The rooms are spacious and modern, but the outside look and feel of the hotel is very quaint. The extremely helpful young woman at the front desk seemed to know everything about the island and was able to answer every question we asked. ..."

Reviewed on Jun 5, 2026

Hotel Moloka'i
Castle at Moloka'i Shores

Castle at Moloka'i Shores

3 out of 5
109 Ala Malama St Kaunakakai HI
Book a stay at this beach condo in Kaunakakai. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Molokai Harbor and Molokai War Memorial ...
7.2/10 Good! (182 reviews)
"In all it was good. A toaster would have been nice and air conditioning"

Reviewed on Jun 2, 2026

Get rates
Castle at Moloka'i Shores
Ocean Front Retreat W/Kitchen-Molokai Shores A308

Ocean Front Retreat W/Kitchen-Molokai Shores A308

Kaunakakai HI
$555 nightly
The price is $650 total per night from Jun 12 to Jun 13
$650 total
Jun 12 - Jun 13
Total with taxes and fees
Stay at this condo in Kaunakakai. Enjoy balconies and an in-room coffeemaker. Popular attractions Molokai War Memorial and Molokai Harbor are located ...
8/10 Very Good! (3 reviews)
"Very nice stay!"

Reviewed on Sep 1, 2025

Ocean Front Retreat W/Kitchen-Molokai Shores A308
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.

Hotels In Kalaupapa

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy Lahaina HI
$309 nightly
The price is $367 total per night from Jun 12 to Jun 13
$367 total
Jun 12 - Jun 13
Total with taxes and fees
Book a stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in ...
8.8/10 Excellent! (4,127 reviews)
"Everything was amazing! The room was clean and spacious! We stayed in a two bedroom on the PH floor, amazing views! The staff was friendly and helpful. Renting snorkel gear, beach chairs, umbrellas and boogie boards was a breeze and Ray was kind and personable down at his little tiki hut! The restaurant ..."

Reviewed on Jun 11, 2026

Aston Kaanapali Shores
Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

4 out of 5
104 Ka'anapali Shores Place Kaanapali HI
$295 nightly
The price is $350 total per night from Jun 21 to Jun 22
$350 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this beach hotel in Kaanapali. Enjoy a beach locale, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,034 reviews)
"I liked how the rooms were kept up. A restaurant is needed on the property. The breakfast included in my package was ok. But not worth the price."

Reviewed on Jun 11, 2026

Hilton Vacation Club Ka'anapali Beach Maui
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive Kapalua HI
$958 nightly
The price is $1,137 total per night from Jun 12 to Jun 13
$1,137 total
Jun 12 - Jun 13
Total with taxes and fees
Book a stay at this luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
9.2/10 Wonderful! (1,003 reviews)
"We loved this hotel. While it's not a classic 'on the beach' resort, beaches are close by and the overall setting is beautiful. We had one of the 'fire lanai' rooms which turned out to be a great choice. The staff was great too. Next time we go to Maui, we plan to stay here again!"

Reviewed on Jun 2, 2026

The Ritz-Carlton Maui, Kapalua
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.

MDW to LUP Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
LUP Address & GPS
Address:
Kalaupapa HI,
United States
IATA Code:
LUP
Longitude:
-156.974444
Latitude:
21.211111
Time Zone:
Pacific/Honolulu

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.