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
$280 nightly
The price is $332 total per night from Sep 6 to Sep 7
$332 total
Sep 6 - Sep 7
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
$521 nightly
The price is $610 total per night from Sep 7 to Sep 8
$610 total
Sep 7 - Sep 8
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
$199 nightly
The price is $237 total per night from Sep 10 to Sep 11
$237 total
Sep 10 - Sep 11
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! (4,291 reviews)
"horrible bar staff, just rude people that work at the bar and restaurant, I also got a call at 11pm while it was quiet hours, from the front desk, then got accused for smoking while it's 11pm.... horrible lol"
Reviewed on Sep 3, 2026
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$858 nightly
The price is $1,019 total per night from Oct 5 to Oct 6
$1,019 total
Oct 5 - Oct 6
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! (1,003 reviews)
"Loved this property. Views were amazing."
Reviewed on Aug 30, 2026
Napili Shores Maui by OUTRIGGER
5315 Lower Honoapiilani Rd Lahaina HI
$231 nightly
The price is $275 total per night from Sep 6 to Sep 7
$275 total
Sep 6 - Sep 7
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! (1,867 reviews)
"Love this place!"
Reviewed on Sep 1, 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 | |
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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.