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
$308 nightly
The price is $366 total per night from Sep 2 to Sep 3
$366 total
Sep 2 - Sep 3
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 ...
7/10 Good! (187 reviews)
"There’s no jacuzzi as advertised. The unit is a bit run down. It was clean and had the basic amenities but needs better maintenance. Overall it was a nice stay."
Reviewed on Aug 24, 2026
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
$525 nightly
The price is $614 total per night from Sep 1 to Sep 2
$614 total
Sep 1 - Sep 2
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
$234 nightly
The price is $278 total per night from Sep 1 to Sep 2
$278 total
Sep 1 - Sep 2
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 ...
Napili Shores Maui by OUTRIGGER
5315 Lower Honoapiilani Rd Lahaina HI
$351 nightly
The price is $417 total per night from Sep 5 to Sep 6
$417 total
Sep 5 - Sep 6
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! (1,866 reviews)
"Our second time at Napili Shores. We were last here in 2014. We came back to celebrate our 30th Anniversary. We had booked a studio but were presently surprised with a one-bedroom unit. Whenever we had a request for more supplies like coffee or shampoo, the Front desk was extremely responsive. We ..."
Reviewed on Aug 31, 2026
Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'anapali Shores Place Kaanapali HI
$259 nightly
The price is $307 total per night from Sep 7 to Sep 8
$307 total
Sep 7 - Sep 8
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! (1,006 reviews)
"Loved almost everything about the hotel. Maybe we got lucky. Partial ocean view and large balcony. Furniture was in good shape. Great location, Times Supermarket (much better than Safeway prices) and ABC Store with Deli (delicious, reasonably priced, cooked Prime Rib lunch or dinners to go) are walking ..."
Reviewed on Aug 31, 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 | |
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Destination Airport | |
Number Of Airlines Serving | |
Distance | |
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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.