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
$236 nightly
The price is $280 total per night from May 28 to May 29
$280 total
May 28 - May 29
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 ...
8.2/10 Very Good! (677 reviews)
"Location on ocean is beautiful. Comfortable room, altho bedding and furniture are worn. Restaurant is closed so only vending machine drinks and snacks are available."
Reviewed on May 17, 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 ...
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
$517 nightly
The price is $606 total per night from May 27 to May 28
$606 total
May 27 - May 28
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
Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'anapali Shores Place Kaanapali HI
$276 nightly
The price is $327 total per night from Jun 14 to Jun 15
$327 total
Jun 14 - Jun 15
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! (1,015 reviews)
"Average resort"
Reviewed on May 25, 2026
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
$342 nightly
The price is $406 total per night from May 29 to May 30
$406 total
May 29 - May 30
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! (4,109 reviews)
"The property was very nice and staff very friendly. Was disappointed you had to pay additional fees to use work out gym. I knew there would be parking fees but any other place I’ve stayed the gym was included."
Reviewed on May 26, 2026
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$958 nightly
The price is $1,137 total per night from May 27 to May 28
$1,137 total
May 27 - May 28
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! (1,002 reviews)
"We are frequent visitors to Kapalua and have always loved the Ritz Carlton. Everything there is superb and close to everything in Kapalua. It is a higher end stay for sure but worth every penny. Could give a higher recommendation!"
Reviewed on May 24, 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.