AI Trip Planner
Plan a trip with
credit card points
Pick origin + destination + month → see best award flights, top hotels bookable on points, attractions, signature events, and the cards whose welcome bonus would cover the trip. 41 US origin airports, no bank link required.
US
Maui, Hawaii
Whales, waterfalls, Road to Hana — Pacific paradise within the US
Pay in cash
$4,200
$700 flight + $3,500 hotel
Pay with points
165,000 pts
+ $30 taxes & fees
Best card for this trip
Chase World of Hyatt
60K bonus + free night cert = ~2 nights at Andaz Maui (~$2,200 value)
Weather in June
🌤️ Shoulder season — decent weather, fewer crowds
Air temp
69°–84°F
21°–29°C
Water temp
78°F
26°C
Rainfall
low
Crowds
Moderate
Warm and dry
Flights — JFK → OGG
EconomyAlaska Mileage Plan
JFK → OGG — long haul — connect via LAX, SFO, or SEA. Alaska miles, JFK-OGG via SEA — best US-Hawaii sweet spot
40,000
roundtrip
+ $30 taxes
American AAdvantage
JFK → OGG — long haul — connect via LAX, SFO, or SEA. AA economy via LAX or DFW
50,000
roundtrip
+ $30 taxes
Open to cover:Sapphire Preferred
Top hotels for your points
Picked for best points value — Hyatt has the only fixed award chart left in major US hotels, so your points stretch the furthest here. Tap each option below for why it stands out.
Hyatt Regency Maui Resort & Spa
Hyatt·Families, big resort vibeCat 5 — large family resort with pools and waterslides.
21K/25K/29K
off / std / peak · Hyatt Cat 6
$700/night cash
5 nights = 125,000 pts (~$3,500 value)
Andaz Maui at Wailea Resort
Hyatt·Luxury beachfront, romanceCat 7 peak; off-peak 35K. Hyatt flagship in Hawaii.
35K/40K/45K
off / std / peak · Hyatt Cat 8
$1100/night cash
5 nights = 225,000 pts (~$5,500 value)
More hotels on points
The Ritz-Carlton Maui, Kapalua
Marriott Bonvoy·Luxury alternative if no Hyatt availabilityDynamic, off-peak 70K. Northern Maui golf resort.
100,000/night
$900/night cash
5 nights = 500,000 pts (~$4,500 value)
Trip Strategy — open these cards and the trip is mostly free
Open World of Hyatt (60K bonus + free Cat 1-4 night cert) + Chase Sapphire Preferred (75K UR transfers to Hyatt + flights). Covers RT flight + 3-4 hotel nights at Andaz Maui.
60K bonus + free night cert = ~2 nights at Andaz Maui (~$2,200 value)
$95/yr annual fee
75K UR → 2 more Hyatt nights OR RT economy flight (40K Alaska)
$795/yr annual fee
Your out-of-pocket budget for this trip
🚗 Car rental needed · vs. $4,200 full cash trip
What to see & do in Maui, Hawaii
Road to Hana
Outdoor64-mile coastal drive with waterfalls, beaches, and rainforest. Allow a full day; rental car required.
Haleakalā Sunrise
Only hereWatch sunrise above the clouds from 10,000 ft volcano summit. Reservations required.
Snorkeling at Molokini Crater
BeachHalf-day boat trips to crescent-shaped marine reserve — turtles and tropical fish.
Lahaina Town
NeighborhoodHistoric whaling town with galleries and oceanfront dining. Recovery ongoing after 2023 fires.
Iao Valley State Park
OutdoorLush valley with iconic 1,200-ft Iao Needle. Short hikes, great photos.
Mama's Fish House
FoodLegendary Pacific Rim seafood right on Kuau Cove. Book months in advance.
Events to know about
- Jun
Maui Film Festival
HappeningWailea Beach in early June; star-studded outdoor screenings.
- Dec · Jan · Feb · Mar · Apr
Maui Whale Watching Season
Humpback whales migrate from Alaska — peak Jan-Mar. Boat tours and shore sightings daily.
- Sep
Aloha Festivals
Statewide cultural celebrations of Hawaiian heritage, music, hula.