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
The price is $324 total per night from Apr 1 to Apr 2
$324 total
per night
Apr 1 - Apr 2
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! (660 reviews)
The room was very clean and the staff members were very friendly and helpful. We had a very relaxing few days stay. But the property does need maintenance and repairs.
Reviewed on Feb 26, 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! (178 reviews)
Location, grounds, pool, oceanside great and maintained. Room not so much. Dirty. Unwashed dishes, cabinets, counters, walls and appliances. So many random kitchen items, needs to be simplified so the poor housekeeper can check them. Long time since the floors were washed, especially to the corners. ...
Reviewed on Feb 5, 2026
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
The price is $473 total per night from Apr 1 to Apr 2
$473 total
per night
Apr 1 - Apr 2
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
The price is $385 total per night from Mar 14 to Mar 15
$385 total
per night
Mar 14 - Mar 15
Book a stay at this beach aparthotel in Kaanapali. Enjoy 2 outdoor pools, a full-service spa, and a beach locale. Our guests praise the pool and the restaurant ...
Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'anapali Shores Place Kaanapali HI
The price is $395 total per night from Mar 22 to Mar 23
$395 total
per night
Mar 22 - Mar 23
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! (1,003 reviews)
Room was clean
Reviewed on Mar 10, 2026
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
The price is $1,683 total per night from Apr 1 to Apr 2
$1,683 total
per night
Apr 1 - Apr 2
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)
Partial ocean view as promised. Food good but not outstanding and food prices were ridiculously high ( $60) for breakfast buffet. It was nice but very busy and noisy at times because of so many people. Nice luxury hotel but didnt always feel like the relaxed pace we have expected from Hawaii.
Reviewed on Mar 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
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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.