Couples Hawaii Vacation Package — Islands of Oahu and Maui

We have contracts nationwide — request a customized quote for your departure airport and travel dates.

Resorts we book

Hotel pictures, room details, and resort pages for this couples itinerary. Open either hotel for more rooms, dining, and photos.

Hilton Hawaiian Village Waikiki Beach Resort — Ocean View King

Check in Hilton Hawaiian Village Waikiki Beach Resort — Waikiki Beach. 5 nights. Sample stay January 24 – January 29, 2027, inside the 01/10/2027 – 06/10/2027 travel window.

• Room 1 — 2 adults
• Room type — Ocean View 1 King Bed, lanai, refrigerator, access to 4 pools
• Welcome lei greeting with round-trip airport transfers
• Flight to Maui included
• Save up to 25% — the discount is already reflected in the vacation price

The Ocean View king is a couples room with a private lanai and a refrigerator. Four pools are in the village, plus Duke Kahanamoku Lagoon and the beach.

Royal Lahaina Resort & Bungalows — Partial Ocean View King

Check in Royal Lahaina Resort & Bungalows — Kaʻanapali Beach. 4 nights. Sample stay January 29 – February 2, 2027.

• Room 1 — 2 adults
• Room type — Partial Ocean View King
• Full-size rental car and taxes included
• Daily breakfast for two and the Myths of Maui luau for two (3-night minimum; this stay is 4 nights)

The Partial Ocean View King is a Lahaina Kai Tower room with a private lanai and a mix of ocean, palm, and West Maui Mountain views. Maui rental car and taxes are included.

Itinerary

Travel window 01/10/2027 – 06/10/2027. Sample dates January 24 – February 2, 2027 — 9 nights, 10 days for 2 adults. Flight from O'Hare nonstop is included. West Coast flights are included from LAX, SFO, SEA, SAN, SJC, and OAK. The sample below is one published schedule so you can see dates and times — we quote your gateway. Airline names and flight numbers are omitted on purpose. Price is based on space availability.

Days	Stay	Notes
Day 1	Fly to Honolulu · Hilton Hawaiian Village	Sunday, January 24, 2027 · 9:30 a.m. – 2:58 p.m. · 9 hr 28 min · O'Hare nonstop
Days 1–5 · Check in	Oahu · Hilton Hawaiian Village	Ocean View 1 King Bed · Waikiki transfers with lei greeting
Day 3	Pearl Harbor from the hotel	Deluxe Arizona Memorial coach tour · hotel pickup · downtown Honolulu pass-by
Day 6	Honolulu to Maui · Royal Lahaina	Friday, January 29, 2027 · 12:40 p.m. – 1:24 p.m. · 44 min
Days 6–9	Maui · Royal Lahaina Resort & Bungalows	Partial Ocean View King · full-size rental car
Day 10	Fly home from Maui	Tuesday, February 2, 2027 · 5:05 p.m. · arrives Wednesday, February 3, 2027 · 5:03 a.m. · 7 hr 58 min

Day 1 — Sunday, January 24, 2027 · Arrive Honolulu

Flight from O'Hare nonstop included. West Coast flights included from LAX, SFO, SEA, SAN, SJC, and OAK. Sample inbound schedule:

• Leaves Sunday, January 24, 2027 · 9:30 a.m. · Chicago O'Hare (ORD)
• Arrives Sunday, January 24, 2027 · 2:58 p.m. · Honolulu, Oahu (HNL)
• Travel time: 9 hr 28 min

Meet your round-trip Waikiki transfer with a welcome lei greeting, then check in Hilton Hawaiian Village Waikiki Beach Resort — 5 nights, check-out January 29.

• Room 1 — 2 adults
• Room type — Ocean View 1 King Bed, lanai, refrigerator, access to 4 pools

Save up to 25%. The discount is already reflected in the vacation price.

Day 2 — Monday, January 25, 2027 · Waikiki at Hilton Hawaiian Village

Ease into the village — Duke Kahanamoku Lagoon, four pools, and Waikiki Beach outside the Ocean View king lanai. Walk Kalakaua Avenue, take a sunset catamaran from the pier, or stay in for Friday-style fireworks later in the week if you are still on Oahu.

Day 3 — Tuesday, January 26, 2027 · Pearl Harbor with hotel pickup

Your third day on Oahu is the Deluxe Pearl Harbor Arizona Memorial and Visitor Center Tour. Hotel pickup is included from Hilton Hawaiian Village — Grand Islander Bus Depot at 8:05 a.m. on this sample morning. Aboard air-conditioned coach, you pass Iolani Palace, the King Kamehameha statue, and Punchbowl National Cemetery with live commentary from your driver-guide. The morning covers the USS Arizona Memorial, the Visitor Center museums, and a downtown Honolulu pass-by, then returns you to the hotel. Upgrade to include the USS Missouri battleship and/or the Pearl Harbor Aviation Museum. Leave bags in the room; none are allowed at the Visitor Center.

Days 4–5 — Wednesday & Thursday, January 27–28, 2027 · More Waikiki

Two open days for the beach, Diamond Head, a snorkel off Waikiki, or a quiet dinner. Ask us to add any Oahu outing to the quote.

Day 6 — Friday, January 29, 2027 · Honolulu to Maui

Check out of Hilton Hawaiian Village and fly to Maui. Flight to Maui included. Sample inter-island schedule:

• Leaves Friday, January 29, 2027 · 12:40 p.m. · Honolulu, Oahu (HNL)
• Arrives Friday, January 29, 2027 · 1:24 p.m. · Maui (OGG)
• Travel time: 44 min

Pick up the included full-size rental car (taxes included) at Kahului Airport, then check in Royal Lahaina Resort & Bungalows — Kaʻanapali Beach. 4 nights, check-out February 2.

• Room 1 — 2 adults
• Room type — Partial Ocean View King
• Daily breakfast for two and the Myths of Maui luau for two
• Maui rental car and taxes included

Days 7–9 — Saturday–Monday, January 30 – February 1, 2027 · Kaʻanapali

Breakfast at Royal Ocean Terrace is included each morning. Use the full-size car for Whalers Village, Black Rock snorkeling, or a drive to Lahaina town. The Myths of Maui luau for two is on property — Hawaiian buffet, open bar, and a Polynesian show. Three pools (two oceanfront) sit between the tower and the sand.

Day 10 — Tuesday, February 2, 2027 · Fly home from Maui

Check out of Royal Lahaina and return the car at Kahului. Sample return schedule (overnight):

• Leaves Tuesday, February 2, 2027 · 5:05 p.m. · Maui (OGG)
• Arrives Wednesday, February 3, 2027 · 5:03 a.m. · Chicago O'Hare (ORD)
• Travel time: 7 hr 58 min

Additional baggage charges may apply. West Coast returns are quoted on the same dates when that gateway is a better fit. Price is based on space availability.

What’s included

• 5 nights Ocean View 1 King Bed at Hilton Hawaiian Village — lanai, refrigerator, access to 4 pools, welcome lei greeting with round-trip airport transfers, flight to Maui included
• 4 nights Partial Ocean View King at Royal Lahaina Resort & Bungalows
• Full-size rental car and taxes included
• Daily breakfast for two and Myths of Maui luau for two
• Maui rental car and taxes included
• Flight from O'Hare nonstop included, West Coast flights from LAX, SFO, SEA, SAN, SJC, OAK included
• Deluxe Pearl Harbor Arizona Memorial and Visitor Center Tour with hotel pickup

Price is based on space availability. We have contracts nationwide — request a customized quote for your departure airport and travel dates.