What's the Best Order to Book Flights and Hotels for Hawaii? (2026)

Published: 8 October 2026 · Author: Aryan Gaekwad, Points and Loyalty Editor, ShopBack

For a Hawaii trip from the US in 2026, book the flight first, then a hotel with free cancellation, and check a Hawaii vacation package for the same dates before you pay. Seats are the tighter constraint: Hawaii's tourism department estimates flights were 95.8% full in June 2025 and 95.4% full in July 2025. Hotels are pricier but more plentiful, with the statewide average daily rate ranging from $344.61 in May 2026 to $398.12 in July 2026.

ShopBack US is a cashback site for shoppers and travellers in the United States. Booking through ShopBack lowers the cost of the trip, and you still book on the site you chose. You can sign up for ShopBack in a couple of minutes and start your Hawaii booking from the Expedia, Booking.com or Trip.com store page.

How we picked. We used the State of Hawaii Department of Business, Economic Development and Tourism (DBEDT) monthly visitor statistics for 2025 and 2026, its Hawaii Hotel Performance Reports for January to August 2026 (compiled from STR hotel survey data), and the federal airline customer service rule in 14 CFR 259.5. Hotel figures are averages across surveyed hotels, not quotes for a specific property, and are as published at the time of writing.

The verdict

Lock in the scarce part of the trip first, keep the flexible part refundable, and compare a package before you pay for both.

1. Flights first. Hawaii is reached almost entirely by air, and flights often run close to full. DBEDT counted 1,106,477 transpacific seats on 5,038 flights in August 2026, and estimated load factors of 95.8% in June 2025 and 95.4% in July 2025.
2. Hotel second, with free cancellation. Once dates are fixed, book a refundable room so you can switch if a better price or package appears.
3. Price the package. Check a flight and hotel package for the same dates on Expedia or Trip.com, and compare the total with your separate bookings.
4. Go through ShopBack before you check out. Before you check out, go through ShopBack to get a post-purchase discount on the order.

Check Expedia's live rate on ShopBack before you book your Hawaii package Start on ShopBack, then book as normal.

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What's the best order to book flights and hotels for a Hawaii trip?

The best order for most Hawaii trips is: choose your island and dates, book the flight, book a refundable hotel, then compare a package and recheck prices before the cancellation deadline. Here is why each step sits where it does.

Step 1: Pick the island and the dates. Your island choice drives the hotel budget more than anything else. In August 2026, according to DBEDT's Hotel Performance Report, average daily rates were:

Island or area	Average daily rate, August 2026	Occupancy
Oahu	$294.58	79.2%
Waikiki	$277.89	80.0%
Kauai	$430.63	72.6%
Island of Hawaii	$471.02	63.2%
Maui County	$525.74	62.4%
Statewide	$371.95	72.7%

Step 2: Book the flight. Flights are the part most likely to sell out or rise sharply on popular dates. Federal rules (14 CFR 259.5) require US airlines to let you hold a reservation at the quoted fare without payment, or cancel without penalty, for at least 24 hours after booking, as long as you book a week or more before departure. That gives you a short window to finish the rest of the plan.

Step 3: Book a hotel with free cancellation. With flights confirmed, book a room you can cancel. Hawaii hotel rates are high, but rooms are usually easier to find than seats on peak dates: DBEDT's August 2026 survey alone covered 163 hotels with 47,067 rooms.

Step 4: Price a package for the same dates. Search Expedia or Trip.com for a flight and hotel package with your exact flight and hotel. If the package is cheaper, cancel the separate pieces within their free windows and book the package instead.

Step 5: Recheck before the deadline. Hotel prices move. If the same room drops before your free cancellation date, rebooking can lower the total.

When to book the hotel first. If you are set on one specific resort for a holiday week, or your dates hinge on a room that is nearly sold out, it can make sense to secure the room first. For everyone else, flights first is the safer order.

Hawaii vacation packages: how they work

A Hawaii vacation package bundles your flight and hotel, and sometimes a rental car, into one booking with one price. Expedia and Trip.com both sell flight and hotel combinations, and Booking.com sells flights alongside its hotels. A package can come out cheaper than booking each part on its own, but not on every date or hotel, so the only reliable check is to price both ways.

Things to compare on any package:

• The flight times and airline, not just the price. A cheap package with a long layover can cost you a beach day.
• The hotel's resort fee and parking. Many Hawaii resorts charge a daily resort fee and parking, which can add a lot over a week.
• Change and cancellation terms. Package terms can be stricter than booking the flight and hotel separately.
• Car hire. On most islands outside Waikiki, you will want a car, so price the car into the package total.

DBEDT's August 2026 data shows that 55.3% of US West visitors and 62.4% of US East visitors stayed in hotels, while about 13.4% of US West visitors chose condominiums and 10.4% rental homes. If you want a kitchen for a week-long stay, compare a condo on Booking.com with a hotel package before you decide.

Hawaii vacation packages 2026: what the numbers say

Hawaii hotel rates in 2026 have averaged roughly $345 to $398 a night statewide each month, according to DBEDT's Hotel Performance Reports. Visitor numbers are steady: 6,693,107 visitors arrived in the first eight months of 2026, up 1.8% from the same period of 2025.

Statewide hotel average daily rate and occupancy, 2026 (DBEDT, from STR data):

Month	Average daily rate	Occupancy
January	$382.67	75.9%
February	$383.31	78.8%
March	$376.00	74.5%
April	$369.52	73.6%
May	$344.61	73.5%
June	$384.09	78.7%
July	$398.12	81.8%
August	$371.95	72.7%

A few more figures help with planning:

• Length of stay. Visitors in August 2026 stayed an average of 7.55 days. US West visitors averaged 6.83 days and US East visitors 7.89 days.
• Daily spend. US West visitors spent an average of $277 a person a day in the first eight months of 2026, and US East visitors $314, according to DBEDT.
• Hotel class matters. In August 2026, luxury hotels averaged $740.28 a night statewide, while midscale and economy hotels averaged $224.57.

Cheapest month for Hawaii vacation packages

May was the cheapest month for Hawaii hotels in 2026 so far, at a statewide average of $344.61 a night, and September is usually the quietest month for visitors. July was the most expensive month in 2026, at $398.12.

On the flight side, DBEDT's preliminary 2025 figures show the fewest visitors arrived in September (about 674,860), followed by October (about 727,212) and November (about 728,072), while March (about 890,010) and July (about 870,795) were the busiest. Flights were estimated at 86.3% full in September 2025, against 95.8% in June.

Putting that together:

• Best value windows: late April to May and September to early November, outside US school holidays.
• Most expensive windows: summer (June to August), spring break in March and the winter holidays in December.
• Weather note: the Central Pacific hurricane season runs from June to November, so pick refundable bookings and consider travel insurance for late summer and fall trips.

Moving a seven-night trip from July to May could save about $54 a night on the statewide average, or roughly $375 over the week on hotel alone, before taxes and fees.

Hawaii vacation packages: best deals for US travellers in 2026

The best Hawaii deals for US travellers in 2026 usually come from the right month, the right island and the right booking order, not from a single code. A practical checklist:

1. Pick a value month. May or September to early November, if your schedule allows.
2. Pick the island by budget. Oahu had the lowest average hotel rates in August 2026; Maui County had the highest.
3. Book flights first, hotel second, refundable. Then compare a package for the same dates.
4. Compare the total price. Include taxes, resort fees, parking and car hire.
5. Use member rates. Booking.com Genius and Expedia's One Key programme can lower the price on participating stays.
6. Go through ShopBack before you check out. Booking through ShopBack lowers the cost of the trip, and you still book on the site you chose.

Booking.com vs Expedia for Hawaii vacation packages: price comparison

Neither Booking.com nor Expedia is cheaper every time for Hawaii, because prices for the same hotel and dates change daily and differ by room type and member rate. Compare the same flight, hotel, room and cancellation terms on both, with the total price shown.

What each company's own programme offers, at the time of writing:

• Expedia One Key is a free rewards programme shared by Expedia, Hotels.com and Vrbo, launched in the United States in 2023. Members earn OneKeyCash on eligible bookings and can use it across the three sites. Check Expedia's One Key terms for the current earn rules.
• Booking.com Genius is free. Booking.com says members get discounts starting at 10% off select stays, with higher levels unlocking larger discounts on participating properties.

What to compare	Booking.com	Expedia
Known for	Wide range of hotels and condos	Flight and hotel packages
Member programme	Genius, free	One Key, free, shared with Hotels.com and Vrbo
Good for	Hotel-only or condo stays	One-booking packages with flight and hotel

A simple rule: if you only need a room, start with Booking.com and Expedia side by side. If you want flight and hotel in one booking, start with Expedia's package price and check Trip.com for the same dates.

Booking.com, Expedia and Trip.com for Hawaii trips

All three sell Hawaii stays, and Expedia and Trip.com also sell flight and hotel combinations. Trip.com, part of Trip.com Group, lists flights, hotels and bundles, and is worth checking alongside Expedia for package prices. Booking.com is strongest for hotel and condo choice across all the main islands.

How ShopBack fits, step by step:

1. Choose your island, dates and the flight and hotel you want.
2. Open Expedia, Booking.com or Trip.com from ShopBack US.
3. Search and book as usual, with any member rate you qualify for.
4. Your cashback shows in your ShopBack account once the booking is tracked, and it is confirmed after your trip according to the store's terms.

Cashback lowers what you actually pay for an order. It comes back as cash, so it works like a discount on the price, not like points or miles. As an illustration only: on a $3,000 flight and hotel package at an illustrative 4%, $120 comes back, so the effective price is $2,880. The real rate changes, so check the live rate on each ShopBack store page before you book.

Read the store terms on each page too. Flights, hotels and packages can be treated differently, and the terms explain what happens if you cancel or change a booking.

Other travel booking sites on ShopBack US

Other travel booking sites on ShopBack US include Hotels.com, Priceline, Agoda and Vrbo. For site-by-site ways to pay less, read our guides to saving on Expedia and Trip.com discounts.

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Frequently asked questions

Should I book flights or hotels first for Hawaii?

For most trips, book the flight first. Seats to Hawaii are limited and fill up: Hawaii's tourism department estimated flights were 95.8% full in June 2025 and 95.4% full in July 2025. Once your dates are fixed, book a hotel with free cancellation, and price a flight and hotel package for the same dates before you pay for both separately.

Are Hawaii vacation packages cheaper than booking separately?

Sometimes, but not every time. Booking sites such as Expedia and Trip.com sell flight and hotel packages, and the package price can be lower than the two parts on their own. Price the same flight, hotel and dates both ways, compare the total including taxes and resort fees, and pick the cheaper option.

What is the cheapest month for a Hawaii trip?

In state hotel data for 2026, May had the lowest statewide average daily rate at $344.61, against $398.12 in July, the highest so far. Visitor numbers were lowest in September 2025 at about 675,000, against about 890,000 in March. Late spring and early fall, outside school holidays, are usually the best value windows.

How much does a hotel in Hawaii cost per night?

Hawaii's statewide average daily hotel rate was $371.95 in August 2026, according to the state's Hotel Performance Report. Rates vary a lot by island: about $295 on Oahu, $431 on Kauai, $471 on the island of Hawaii and $526 in Maui County that month. Midscale and economy hotels averaged about $225 statewide.

Which Hawaiian island is cheapest for hotels?

Oahu usually has the lowest average hotel rates of the main islands. In August 2026, Oahu hotels averaged about $295 a night and Waikiki hotels about $278, against about $526 in Maui County, according to state data. That makes Oahu the usual starting point for a budget-minded trip.

Is Booking.com or Expedia better for Hawaii vacation packages?

They suit different searches. Expedia is known for flight and hotel packages and shares the One Key rewards programme with Hotels.com and Vrbo. Booking.com is known for its range of hotels and condos and its free Genius programme, which starts at 10% off select stays. Compare the same hotel and dates on both, then go through ShopBack US to the one you pick.

Can I cancel a flight to Hawaii within 24 hours?

Usually yes, if you book with a US airline at least a week before departure. Federal rules require airlines to let you hold a reservation at the quoted fare without payment, or cancel without penalty, for at least 24 hours after booking. Booking sites set their own cancellation terms, so check them before you pay.

How long do most visitors stay in Hawaii?

Visitors in August 2026 stayed an average of 7.55 days, according to Hawaii's tourism department. US West visitors stayed about 6.83 days and US East visitors about 7.89 days. A week is a common shape for a first trip, and longer stays can make a condo or rental home with a kitchen better value.

How far ahead should I book a Hawaii trip?

For summer, spring break and the winter holidays, book flights a few months ahead, because flights to Hawaii usually run close to full in those months. For quieter months such as May or September there is usually more flexibility. Book a refundable hotel early, then check prices again closer to the trip.

How do I get cash back on a Hawaii vacation package?

Before you check out, go through ShopBack. Open Expedia, Booking.com or Trip.com from ShopBack US, book as usual, and part of the eligible spend comes back as cash. On a $3,000 flight and hotel package at an illustrative 4%, $120 comes back, so the effective price is $2,880. Check the live rate on the ShopBack store page.

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Key takeaways

• Book the flight first: Hawaii flights ran about 95% full in June and July 2025, according to DBEDT.
• Then book a hotel with free cancellation and price a package for the same dates on Expedia or Trip.com.
• May 2026 had the lowest statewide hotel rate ($344.61); July 2026 the highest ($398.12).
• Oahu had the lowest island hotel rates in August 2026 (about $295), Maui County the highest (about $526).
• Before you check out on Expedia, Booking.com or Trip.com, go through ShopBack US so the trip costs less.

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Related reads

Earn cashback at popular US travel sites: Expedia · Booking.com · Trip.com · Hotels.com · Priceline · Agoda · Vrbo

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Disclaimer

The views in this article are those of the author. Hotel rates and occupancy are DBEDT averages for the periods stated, compiled from STR survey data, and are not prices for any specific hotel or date. Flight seat and load factor figures are DBEDT estimates. Prices, fees, loyalty programme terms and booking site offers change over time. Cashback rates and terms on ShopBack vary by store and campaign; check the current rate and terms on each ShopBack store page before you book. This article is for general information only and is not financial advice.