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
$250 nightly
The price is $297 total per night from Jul 27 to Jul 28
$297 total
Jul 27 - Jul 28
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! (690 reviews)
"Love this property and will keep staying here 💕🙌"
Reviewed on Jul 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 ...
7/10 Good! (186 reviews)
"We arrived in Molokai at 3:00 p.m. Our rental car had a flat tire so they brought us a new one by the time this happened we missed the check-in time at Molokai Shores by 4:00 p.m. she went home and I could not find our room we had no cell phone service so we could not contact her. A local girl ended ..."
Reviewed on Jul 24, 2026
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
$525 nightly
The price is $614 total per night from Aug 23 to Aug 24
$614 total
Aug 23 - Aug 24
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
$236 nightly
The price is $281 total per night from Jul 31 to Aug 1
$281 total
Jul 31 - Aug 1
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! (4,202 reviews)
"Clean, everything you need right there! Our family of 5 stayed in a 2 bedroom suite that was gorgeous and had a kitchen and washer/dryer. The restaurant food wasn't the best but it was so ice to have it right there onsite as an option! We rented snorkels and beach gear right at the resort! The beach ..."
Reviewed on Jul 26, 2026
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$858 nightly
The price is $1,019 total per night from Jul 31 to Aug 1
$1,019 total
Jul 31 - Aug 1
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)
"The stay was comfortable with different dining options and activities (i.e., pool, beach, hiking trails, etc.) near by. It's definitely a place to relax."
Reviewed on Jul 26, 2026
Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'anapali Shores Place Kaanapali HI
$267 nightly
The price is $317 total per night from Aug 23 to Aug 24
$317 total
Aug 23 - Aug 24
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 ...
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.