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
$257 nightly
The price is $305 total per night from Oct 13 to Oct 14
$305 total
Oct 13 - Oct 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 ...
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
$525 nightly
The price is $614 total per night from Sep 13 to Sep 14
$614 total
Sep 13 - Sep 14
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 13 to Sep 14
$1,019 total
Sep 13 - Sep 14
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! (1,001 reviews)
"Outstanding property. Five star in every way. Exceptional hospitality in the true Ritz Carlton style."
Reviewed on Sep 10, 2026
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
$204 nightly
The price is $242 total per night from Sep 17 to Sep 18
$242 total
Sep 17 - Sep 18
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! (4,306 reviews)
"Nice grounds and location."
Reviewed on Sep 12, 2026
Napili Shores Maui by OUTRIGGER
5315 Lower Honoapiilani Rd Lahaina HI
$247 nightly
The price is $294 total per night from Sep 14 to Sep 15
$294 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! (1,872 reviews)
"Property was nice but is more like a condo rental than "resort". The view from my room was beautiful and not too far from free parking. The room is very large with a stand up shower, decent kitchen, tv, and lanai. However the Murphy Bed was super hard and uncomfortable. I had a back ache every day ..."
Reviewed on Sep 12, 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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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.
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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.