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
1300 Kamehameha V Hwy Kaunakakai HI
$251 nightly
The price is $298 total per night from Jun 11 to Jun 12
$298 total
Jun 11 - Jun 12
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! (678 reviews)
"Clean and functional room, although not luxurious. A terrific view from upper unit. Minimal amenities (no restaurant on site but a new one is in the plans for summer 2026). The property evokes “Old Hawaii” nostalgia and vibes. It’s the only hotel on the island."
Reviewed on May 27, 2026
Castle at Moloka'i Shores
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
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
$524 nightly
The price is $613 total per night from Jun 5 to Jun 6
$613 total
Jun 5 - Jun 6
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
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
Hilton Vacation Club Ka'anapali Beach Maui
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! (1,017 reviews)
"Room is very clean, wonderful staff. Our room floor had laundry too. Perfect for family vacation"
Reviewed on Jun 3, 2026
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$958 nightly
The price is $1,137 total per night from Jun 4 to Jun 5
$1,137 total
Jun 4 - Jun 5
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
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
$444 nightly
The price is $527 total per night from Jun 4 to Jun 5
$527 total
Jun 4 - Jun 5
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! (4,118 reviews)
"What truly sets the resort apart is its exceptional staff, who provide genuinely warm, anticipatory service. It is a flawless, highly recommended slice of paradise that is worth every penny."
Reviewed on Jun 2, 2026
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
- O'Hare Intl. Airport (ORD)
- Chicago Executive Airport (PWK)
- Dupage Airport (DPA)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- General Mitchell Intl. Airport (MKE)
- Waukesha County Airport (UES)
- Goshen Municipal Airport (GSH)
- Purdue University Airport (LAF)
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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.