Hawaii on points
A weeklong Hawaii vacation runs $4,000-6,000 in cash. The same trip on points is closer to $400-700 — flights nearly free, luxury resorts at half-price, and elite benefits that turn good hotels into great ones. Here’s exactly how to plan it.
By the end of this guide
- The total cost comparison: $5,000 cash trip vs. $500 points trip — concrete math
- Which Hawaiian island is best for your trip style (Maui, Oahu, Big Island, Kauai)
- The four best programs for booking flights to Hawaii — ranked by point cost
- Six specific properties to target on points, with cash vs. point rates for each
- The full Hawaii points playbook — exact sequence, start to finish
- When to go for the best award availability and lowest point pricing
- A sample 7-day Maui itinerary built entirely on points
- The five mistakes new points travelers make on Hawaii trips
The Hawaii math is wild
Hawaii is one of the best points-and-miles destinations on the planet for U.S. travelers, and the reason is simple: cash prices are punishing. Flights routinely run $600-1,200 round-trip even from the West Coast. Mid-range hotels start at $300/night. Top-tier resorts run $700-1,500/night during peak season. A typical family of four can easily spend $6,000-10,000 cash for a week.
Now look at the same trip on points. Round-trip flights at 20,000 miles per person. Hyatt Cat 4-6 properties at 15,000-25,000 points per night. The savings aren’t incremental — they’re structural. You’ll pay less than a tenth in cash, and the experience is often better than the cash version because elite status unlocks upgrades, breakfast, and waived resort fees that paid customers don’t get.
Sample 7-day Hawaii trip — cash vs. points
Couple, late September shoulder season, Maui
What you’d actually pay
- Round-trip flights (2)$1,400
- 6 nights, Andaz Maui$3,900
- Resort fees (6 × $50)$300
- Rental car (7 days)$420
- Meals + activities$1,000
- Total cash cost$7,020
What you’d actually spend
- 40K Chase UR → United~$22 fees
- 180K Chase UR → Hyatt$0
- Resort fees (Globalist)$0
- Rental car (cash)$420
- Meals + activities$1,000
- Total out-of-pocket$1,442
Total savings: roughly $5,580. The points used (220K Chase UR total) can be earned from welcome bonuses on the Sapphire Preferred plus the Sapphire Reserve — and once you’re Globalist with Hyatt, those waived resort fees alone save another $300+. This is the points-and-miles dream realized in one trip.
Choose your island
Hawaii has four main islands accessible to most travelers — and they’re genuinely different experiences. Picking the right island for your trip type and points stash makes a meaningful difference.
Maui — the all-rounder
The most popular island for first-time visitors. Beautiful beaches, the Road to Hana, Haleakalā volcano, and easy access to whale-watching, snorkeling, and fine dining. The Andaz Maui at Wailea is the marquee Hyatt property — one of the best hotel redemptions in points and miles.
Oahu — Waikiki and beyond
Honolulu and Waikiki Beach offer urban energy, but the island’s North Shore and windward coast deliver real wilderness. Best variety of points hotel options including the cheap-but-reliable Hyatt Place Waikiki (Category 1) — making it the most accessible island for budget points travelers.
Big Island — diverse and dramatic
Active volcanoes, black sand beaches, lush rainforests, and astronomical observatories on Mauna Kea. Less developed than Maui or Oahu — fewer points hotel options but the experiences are unique. Good for travelers who want adventure over resort relaxation.
Kauai — the Garden Isle
Lush, quiet, and dramatically beautiful — Na Pali Coast, Waimea Canyon, secluded beaches. Smaller resort selection means fewer points options, but the Grand Hyatt Kauai is one of the best points properties anywhere in Hawaii. Best island for nature-focused travelers who want fewer crowds.
If this is your first Hawaii trip: start with Maui or Oahu. They have the most points hotel options, the easiest flight access, and the broadest range of activities. Save the Big Island and Kauai for return visits — they reward travelers who already know what Hawaii offers.
Getting to Hawaii on points
Flights to Hawaii are where the cash savings are most dramatic. A cash ticket from the West Coast typically runs $400-800 round-trip; from the East Coast, $700-1,200. Both can be booked for 20,000-25,000 miles round-trip on the right program.
Here are the four best programs for booking Hawaii flights, ranked by typical point cost and availability:
United MileagePlus — the workhorse
20,000-25,000 miles round-trip economy from the West Coast; 30,000 from the East Coast. The most reliable availability on Hawaii routes. Transfer from Chase Ultimate Rewards at 1:1. United operates most Hawaii routes year-round.
Hawaiian Airlines — destination expert
Operates the most routes to and within Hawaii. HawaiianMiles transfer from Amex Membership Rewards at 1:1. Inter-island flights from 7,500-10,000 miles one-way — useful if you want to island-hop on a single trip.
Alaska Airlines Mileage Plan
Strong West Coast routes to all major Hawaiian airports. 20,000 miles round-trip economy from West Coast cities. Stopovers allowed on awards — book a one-week stay in Hawaii with a stopover en route to or from Asia or beyond.
Southwest Rapid Rewards — wildcard
Variable pricing tied to cash fare — sometimes excellent (12,000-18,000 points round-trip) when cash prices are low; less competitive when fares spike. Transfer from Chase UR at 1:1. Companion Pass holders can bring a partner for free.
The flight strategy: book first, then hotels
Award flight availability to Hawaii is more constrained than hotel availability — particularly during peak seasons. Book your flights first, then build your hotel stay around the dates that worked. Don’t lock in hotel dates and then try to find flights — that’s how new points travelers end up paying cash for flights because no awards exist on their target dates.
Where to stay on points — six specific properties
These are the properties our team has either stayed at or repeatedly recommends to readers. Cash rates are based on typical peak-season pricing (late June through early September and December holidays). Off-peak pricing in shoulder seasons can be 20-30% lower on both cash and points.
Andaz Maui at Wailea — the marquee
The Hyatt property points travelers obsess over. Beachfront location in Wailea on Maui’s southwest coast, four pools cascading down to the ocean, exceptional dining, and the kind of service that makes you understand why people return year after year. Cash rates routinely exceed $900/night in peak season; 30,000 points/night standard. Globalist breakfast at Ka’ana Kitchen is one of the best hotel breakfasts in Hawaii.
Grand Hyatt Kauai — the romantic choice
Sprawling resort on Kauai’s south shore. Saltwater lagoon pools, a quiet beach, and lush gardens that make it feel like a separate world. Smaller than Andaz Maui but with the same Globalist benefits. The luau here is one of the best hotel-hosted ones in Hawaii. 30,000 points/night vs. cash rates of $700-1,000.
Hyatt Regency Maui Resort & Spa
Located on Ka’anapali Beach on Maui’s northwest coast. Larger and more family-friendly than the Andaz, with more pools, a 130-foot waterslide, and a 0.5-acre swimming complex. Better value at 25,000 points/night standard. Note: check operations status given regional impacts from the 2023 fires.
Hyatt Place Waikiki Beach — the budget hero
The unsung hero of points-based Hawaii travel. Off-peak: 3,500 points/night. Standard: 5,000 points/night. Free breakfast, walking distance to Waikiki Beach, and reliable Hyatt service. Cash rates run $200-280/night. For a week-long Oahu trip, you can book 7 nights here for under 35,000 points — the best per-point value in any Hawaii Hyatt property.
The Ritz-Carlton Maui, Kapalua
Marriott’s premier Maui property on the northwest coast. Larger property, more amenities than Andaz, with a different vibe — more traditional luxury versus Andaz’s modern feel. Marriott’s dynamic pricing means point costs vary widely (typically 80,000-130,000 points/night), but the property is consistently exceptional. Free 5th night when redeeming with points.
Sheraton Maui Resort & Spa
Mid-tier Marriott property at Black Rock on Ka’anapali Beach. Lower point cost than the Ritz (typically 50,000-80,000 points/night), great snorkeling right off the beach, and the famous nightly cliff-diving ceremony. Best Marriott property in Maui at this point level if dynamic pricing is favorable.
The pattern that emerges: Hyatt properties consistently deliver 2.5-4.5¢ per point of value in Hawaii — at the very high end of what’s possible in points-and-miles redemptions. Marriott properties in Hawaii hover around 0.7-0.9¢ per point because of dynamic pricing. If you have any access to Chase Ultimate Rewards points, transfer them to Hyatt for your Hawaii hotel stays — the math is unbeatable.
The complete Hawaii points playbook
Here’s the exact sequence for executing a points-based Hawaii trip. Follow this order — getting it out of sequence creates problems that compound.
Earn the points first (4-8 months out)
You need roughly 220-280K Chase Ultimate Rewards points for a solid Hawaii trip — flights for two plus a week of Hyatt nights. The fastest path: open a Chase Sapphire Preferred ($95 fee, 60K welcome bonus) and a Chase Sapphire Reserve ($795 fee, but most of that offset by credits), hit the minimum spend on both, and you’ll have 150-220K UR before counting any normal earnings. Add a Freedom card for everyday spending to top off.
Pick your dates with flexibility (3-4 months out)
The sweet spot is late April through late May or September through early November — shoulder seasons with the best award availability, lowest off-peak point pricing on hotels, and still-excellent weather. Avoid the school holiday windows (mid-June through August, Thanksgiving week, Christmas through New Year). Stay flexible across a 2-3 week window for best results.
Search and book your flights (3-4 months out)
Use our award travel guide to search availability across United, Hawaiian, Alaska, and Southwest. Book flights before hotels — flight availability is the bigger constraint. Once you have specific flight dates confirmed, you can search hotels for those exact nights.
Confirm hotel availability (2-3 months out)
Search Hyatt’s website directly for your chosen property and dates. Confirm the points cost (categories shift occasionally, and peak/off-peak pricing applies). Note the exact points needed before transferring anything. Don’t transfer UR points until availability is confirmed at the rate you’re targeting.
Transfer Chase UR to Hyatt and book (immediately)
Transfer the exact number of points needed (1:1 ratio) — don’t over-transfer. Once points hit your Hyatt account (usually instant), book immediately. Pay any taxes/fees with a card that offers trip insurance (Sapphire Reserve, Sapphire Preferred).
Add the optimizations (1-2 months out)
If you have Globalist status, your stay automatically includes free breakfast for 2, suite upgrades when available, waived resort fees on points stays, and 4 PM late checkout. If you don’t have Globalist yet, see if any of the Hyatt credit cards can fast-track you. Book rental car in cash; book activities directly with operators.
The best time to go (for points travelers)
For cash travelers, the calculus is mostly about weather and crowds. For points travelers, three additional factors weigh in: award availability, off-peak vs. peak point pricing, and Globalist resort fee waivers.
Shoulder season sweet spots
Late April through late May and September through early November are the two ideal windows. Weather is still excellent (Hawaii’s “wet” season is technically October-March but rarely affects beach vacations meaningfully). Award flight availability is much better than peak season. Off-peak point pricing on Hyatt properties drops the cost of an Andaz Maui night from 30K to about 24-26K. And crowds are noticeably lighter.
Peak season (avoid if possible)
Mid-June through mid-August and the weeks around Thanksgiving, Christmas, and New Year’s are the worst times for points travelers. Award flight availability dries up. Hyatt properties shift to peak pricing (30K → 35K+ at Andaz Maui). Resort fees are at peak rates. Cash rates double. If you can shift your trip by 2-3 weeks, do it — the savings in points (and stress) are substantial.
The whale-watching exception
If whale-watching is important to you, December through April is the only window when North Pacific humpbacks are in Hawaiian waters. February-March is peak season for whale sightings. The points math gets harder in this window, but for a once-in-a-lifetime whale encounter, it can be worth it.
Five common Hawaii mistakes
These patterns trip up new points travelers consistently. Avoid all five and your Hawaii trip will go smoothly.
Booking hotels before confirming flight awards
Award flight availability is the binding constraint on most Hawaii trips. If you lock in hotel dates first and then find no award flights, you’ve boxed yourself in. Always book flights first, then build hotel dates around the flights that worked.
Transferring Chase UR to Hyatt “in advance”
Don’t transfer points to Hyatt until you have a specific room confirmed and ready to book. Once Chase UR points become World of Hyatt points, they’re stuck there — you can’t transfer them back. If availability disappears or your plans change, your Hyatt points have less flexibility than Chase UR did. Cardinal rule applies.
Choosing Marriott over Hyatt by default
Marriott has more properties in Hawaii than Hyatt, so it feels like the obvious choice. But Marriott’s dynamic pricing eats away at point value — typical Marriott redemptions in Hawaii hover at 0.7-0.9¢ per point, while Hyatt redemptions deliver 2.5-4.5¢ per point. For most points travelers, Hyatt wins decisively in Hawaii — even when it requires staying at the property a 30-minute drive from where Marriott had a closer option.
Underestimating the rental car cost
You’ll need a car on every Hawaiian island except possibly Oahu (where Waikiki is walkable). Rental cars in Hawaii are expensive — frequently $80-120/day during peak season — and there’s no good way to book them on points. Budget cash for the rental and factor it into your trip total. National Car Rental’s Emerald Club tier (free with most premium cards) helps skip the counter.
Trying to do too many islands in one trip
Hawaii’s islands are close enough geographically that travelers try to do 2-3 in a week. Don’t. Each island deserves at least 4-5 days to settle in, and inter-island travel eats more time than people expect (airport security, flights, baggage, car rental switches). Pick one island for your first trip. Save the others for return visits — you’ll have plenty of motivation to return.
A sample 7-day Maui itinerary on points
Here’s a concrete example of how a week-long Maui trip might unfold for a couple traveling in late September. Total cost: roughly $1,400 out of pocket plus 220K Chase Ultimate Rewards points.
7 days, 6 nights — Maui in shoulder season
Couple, late September, Andaz Maui base camp
Arrival & settle in
West Coast morning departure, mid-afternoon arrival at OGG (Kahului). Rental car pickup, 45-minute drive to Wailea. Check in at Andaz Maui — request a suite upgrade if you’re Globalist. Sunset at the pool, dinner at Morimoto Maui.
Beach day + south coast
Globalist breakfast at Ka’ana Kitchen (saves $80). Morning at Wailea Beach. Lunch at Monkeypod Kitchen in Wailea Village. Afternoon snorkel at Makena Beach. Dinner at one of Wailea’s resort restaurants.
Road to Hana (full day)
Early breakfast at the hotel, leave by 7 AM. Stops at Twin Falls, Wai’anapanapa State Park’s black sand beach, lunch in Hana town, the Seven Sacred Pools. Long but spectacular drive — return to Wailea by sunset.
Haleakalā sunrise + recovery
Pre-dawn drive (or organized tour) to Haleakalā summit for sunrise. Back at the hotel by 10 AM for a long pool afternoon. Spa appointment at ‘Awili Spa & Salon. Casual dinner in Wailea.
Snorkel cruise to Molokini
Half-day Molokini crater snorkel cruise (~$150/person — book in advance). Afternoon at the hotel. Sunset cocktails at The Restaurant at Hotel Wailea or in-resort dining.
West side day trip
Drive to Lahaina-Ka’anapali area (about 45 minutes from Wailea). Beach time at Ka’anapali, lunch at Leoda’s Pie Shop, drive the back road past Honolua Bay to Kapalua. Sunset at Merriman’s Kapalua.
Last beach day + departure
Final Globalist breakfast. Pool morning at the hotel — Globalist 4 PM late checkout means no rush. Drive back to OGG for evening flight home. East Coast travelers can use the daytime flight east; West Coast travelers get the red-eye.
Total trip cost: 40K UR for flights + 180K UR for 6 nights Andaz Maui + ~$420 rental car + ~$22 in flight taxes + ~$1,000 meals/activities = ~$1,442 out of pocket plus 220K Chase UR points. The equivalent cash trip: $7,000+.
The fastest path to Hawaii is the Sapphire Preferred
For most readers, the Chase Sapphire Preferred is the right starting card for a Hawaii trip. Its $95 annual fee, 60,000-point welcome bonus, and 1:1 transfer to both United (for flights) and Hyatt (for hotels) make it the most efficient single-card path to a points-funded Hawaii vacation. Pair it with the Sapphire Reserve for the second welcome bonus and you have most of the points you need.
Read our Sapphire Preferred review →Hawaii on points FAQ
How many points do I need for a week in Hawaii?
For two people: roughly 40,000-50,000 miles for flights (United MileagePlus, transferred from Chase UR) plus 100,000-200,000 hotel points (Hyatt) depending on which property and category. A solid baseline is 220-280K Chase Ultimate Rewards points total, which earns out from welcome bonuses on the Sapphire Preferred ($95 fee, 60K bonus) + Sapphire Reserve ($795 fee but mostly offset by credits, plus a 100K bonus). Add the Freedom or Freedom Unlimited for ongoing earning.
Is it worth flying premium cabin to Hawaii?
Most points travelers say no. Domestic premium cabins (United Polaris doesn’t fly Hawaii routes; United First/Hawaiian First are wide but not lie-flat) require 2-3x the points of economy for incremental improvement. Save your premium cabin points for international long-haul. For Hawaii, the better play is economy on points (saving 80% of the cash cost) and putting the saved cash toward the hotel experience.
Can I use points for the rental car?
Mostly no. Capital One and Chase travel portals let you redeem points at 1¢ for rental cars (the worst use of points). The better play: pay cash for the rental car using a premium card that includes primary rental car insurance (Sapphire Reserve, Venture X) and skip the rental car company’s overpriced coverage. Hertz President’s Circle status (included with Venture X) speeds up the counter experience.
What’s the cheapest Hawaii points trip possible?
Two people, one week on Oahu, at the Hyatt Place Waikiki (5K points/night standard, 3.5K off-peak): roughly 35K Hyatt points for 7 nights. Add 40K United miles for 2 round-trip flights, and you’re at 75K total points + ~$20 in taxes. That’s well under one welcome bonus from the Sapphire Preferred alone. The total cash cost equivalent: $2,500-3,000.
Should I get the World of Hyatt credit card before a Hawaii trip?
For a single Hawaii trip, probably not — the Sapphire Preferred or Reserve gets you Hyatt access at 1:1 transfer with broader flexibility. For someone planning multiple Hyatt-heavy trips per year, the World of Hyatt Credit Card ($95 fee) offers an anniversary free night at Category 1-4 (worth ~$150-200), 4x earning at Hyatt, and easier path to Globalist status through 2 elite night credits + 2 more per $5K spent. Worth holding long-term if you’re a Hyatt loyalist.
How does Globalist status change a Hawaii trip?
Substantially. Globalist benefits at any Hawaii Hyatt include: free daily breakfast for 2 (worth $80-100/day at Andaz Maui), waived resort fees on points stays (~$50/night savings), 4 PM late checkout guaranteed, suite upgrades when available, and free parking. On a 6-night stay at Andaz Maui, Globalist typically saves $700-1,000 in real cash beyond the point savings. Our Hyatt guide covers the full Globalist value.
What if award availability isn’t there for my preferred dates?
Try the same dates in April or September — shoulder seasons have much better availability than peak. If you must travel during a specific window, consider booking a less-premium property on points and saving the marquee property for a future trip. The Hyatt Place Waikiki almost always has availability and still delivers a great trip. You can also book the Andaz Maui via cash if availability is gone — and save your points for a future trip with better timing.
Are there any all-inclusive options like Hyatt Ziva on Hawaii?
No. Hyatt Ziva and Zilara properties exist in Mexico, Jamaica, and Dominican Republic but not Hawaii. The all-inclusive concept doesn’t really exist in Hawaii — even the most premium resorts charge à la carte for food and activities. If you want a true all-inclusive on points, look at our Mexico destination guide instead.
Related guides
The pages most useful for actually executing a Hawaii points trip: