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
$292 nightly
The price is $346 total per night from Oct 25 to Oct 26
$346 total
Oct 25 - Oct 26
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! (697 reviews)
"The hotel grounds were veery well kept. Walking around the property had that authentic Hawaiian feel."
Reviewed on Oct 1, 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! (190 reviews)
"good unit right on water. - bad internet - needed some repairs. screens. refrid, stove. lot of bugs"
Reviewed on Oct 7, 2026
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
$525 nightly
The price is $614 total per night from Oct 14 to Oct 15
$614 total
Oct 14 - Oct 15
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
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
$256 nightly
The price is $304 total per night from Oct 28 to Oct 29
$304 total
Oct 28 - Oct 29
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 ...
Aston Mahana at Kaanapali
110 Ka'anapali Shores Place Kaanapali HI
Book a stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition ...
9/10 Wonderful! (1,849 reviews)
"The location is amazing, right on the beach, very quiet, and serene. Steps to the beach where it’s best for snorkeling and swimming. We got to see sea turtles in the ocean. The rooms are outdated and unfortunately ours had roaches. We enjoyed our stay but would prefer updated/renovated furniture ..."
Reviewed on Oct 13, 2026
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$958 nightly
The price is $1,137 total per night from Oct 14 to Oct 15
$1,137 total
Oct 14 - Oct 15
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 ...
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
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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
Other Flights from Midway Intl. Airport (MDW)
- 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.