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
$246 nightly
The price is $292 total per night from Sep 14 to Sep 15
$292 total
Sep 14 - Sep 15
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 ...
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 ...
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
$524 nightly
The price is $613 total per night from Sep 11 to Sep 12
$613 total
Sep 11 - Sep 12
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
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$858 nightly
The price is $1,019 total per night from Sep 11 to Sep 12
$1,019 total
Sep 11 - Sep 12
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! (1,000 reviews)
"Stay was comfortable staff very attentive & accomodating, We stayed in the fire lanai deluxe room (ocen-view) it was amazing. Be prepared to get your steps in going from your room to the main lobby if you’re staying over there, but you will have easy access to the pool and the exclusion will be very ..."
Reviewed on Sep 7, 2026
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
$204 nightly
The price is $242 total per night from Sep 18 to Sep 19
$242 total
Sep 18 - Sep 19
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! (4,302 reviews)
"Clean room, fully equipped, laundry set with complimentary laundry detergent, ice maker, and spacious. Only thing is the salon restroom could be more equipped for those with late flights, such as lotion, toiletries to use, hair dryers, and a sturdy shower curtain. Mine fell on me a few times while ..."
Reviewed on Sep 9, 2026
Napili Shores Maui by OUTRIGGER
5315 Lower Honoapiilani Rd Lahaina HI
$246 nightly
The price is $292 total per night from Sep 14 to Sep 15
$292 total
Sep 14 - Sep 15
Total with taxes and fees
Book a stay at this beach aparthotel in Napili. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,871 reviews)
"Not a bad view, but no direct access to ocean. Has a cliff with rocks. Beach access is further away to the right. Room had ants coming in n out of back sliding door and also small tiny bugs/lice. Which are probably harmless but kinda gross cuz they were even inside the microwave and were resistant ..."
Reviewed on Sep 9, 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
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Destination Airport | |
Number Of Airlines Serving | |
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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.