Cheap flights from MDW to LUP (Midway Intl. to Kalaupapa)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
Hotel Ideas near Kalaupapa
Airport Hotels near Kalaupapa
Hotel Moloka'i
1300 Kamehameha V Hwy Kaunakakai HI
$254 nightly
The price is $299 total per night from Dec 17 to Dec 18
$299 total
Dec 17 - Dec 18
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! (642 reviews)
Plenty of safe, free parking. The staff was friendly and helpful.
Reviewed on Dec 3, 2025
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! (170 reviews)
better clean room,
Reviewed on Oct 22, 2025
Ocean Front Retreat W/Kitchen-Molokai Shores A308
Kaunakakai HI
$404 nightly
The price is $470 total per night from Dec 17 to Dec 18
$470 total
Dec 17 - Dec 18
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
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$854 nightly
The price is $1,007 total per night from Dec 19 to Dec 20
$1,007 total
Dec 19 - Dec 20
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 ...
9/10 Wonderful! (1,001 reviews)
The breakfast menus were fresh everyday.
Reviewed on Dec 5, 2025
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
Lahaina HI
$761 nightly
The price is $887 total per night from Dec 23 to Dec 24
$887 total
Dec 23 - Dec 24
Total with taxes and fees
Book a stay at this beach condo in Kaanapali. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Kaanapali Beach and Black Rock are located ...
10/10 Exceptional! (207 reviews)
Wonderful unit, great communication by Sandy, and unparalleled views. We had a great experience all around!
Reviewed on Nov 25, 2025
Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'anapali Shores Place Kaanapali HI
$309 nightly
The price is $365 total per night from Dec 18 to Dec 19
$365 total
Dec 18 - Dec 19
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 ...
8.8/10 Excellent! (1,003 reviews)
Everything! Everyone was so friendly and professional ! Shantell was super helpful and knowledgeable in helping us book our excursions. Our Housekeeper was amazing and left our room immaculate ! The Bellmen super nice and helpful and friendly. Overall , I give the Hotel a 10 !
Reviewed on Dec 12, 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.
MDW to LUP Route Info
Origin Airport | |
|---|---|
Destination Airport | |
Number Of Airlines Serving | |
Distance | |
Shortest Flight Departure Time | |
Shortest Flight Departure Date |
- Route Reviews
- Airport Locations
- More Popular Flights
- Top Trending
- Flights from Other Cities
- Flights From Other Airports
- Great Travel Ideas
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)
Top Trending
Flights
- LGA to OGG
- SAN to OGG
- Cheap Charlotte to Milwaukee flights
- Flights to Lanzarote
- Cheap Washington to Ann Arbor flights
- MUM to MWA
- ONT to OGG
- LAX to OGG
- Cheap Chicago to Florida Keys flights
- Cheap Miami to Montreal flights
- Cheap San Francisco to Edmonton flights
- PDX to OGG
- Cheap Denver to Gunnison flights
- Cheap Toronto to Panama City flights
- LGB to OGG
- SFO to OGG
- MSP to OGG
- Cheap Washington to Rio de Janeiro flights
- OGG to KOA
- HNL to OGG
- SMF to OGG
- Cheap Tucson to Detroit flights
- SNA to OGG
- Cheap Ndola to Lusaka flights
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.