Hawaii is the ultimate points and miles destination. It’s far enough to make paid tickets expensive ($500-1,000+ round-trip), but close enough that award availability is usually decent. Plus, multiple programs offer sweet spots that make the islands incredibly accessible with the right strategy.
Whether you’re planning a honeymoon in Maui, a family trip to Oahu, or a solo adventure to the Big Island, here’s exactly how to get there using points and miles in 2026.
Key Takeaways
- Best economy value: Southwest at 20-30K round-trip with no blackout dates
- Best business class: Hawaiian Airlines 787 lie-flat from 80K round-trip via Virgin Atlantic
- Most flexible: United MileagePlus with multiple daily flights
- Best for families: Southwest Companion Pass = 2-for-1 flights
Overview: Hawaii Award Flight Options
| Program | Economy RT | Business RT | Best For |
|---|---|---|---|
| Southwest | 20-35K | N/A | Value, families |
| United | 45K | 160K | Availability |
| American | 45K | 160K | West Coast flyers |
| Delta | 40-80K | 150K+ | Flexible dates |
| Hawaiian (via Virgin) | 40K | 80K | Lie-flat experience |
| Alaska | 40K | 100K | Partner options |
1. Southwest Rapid Rewards (Best Value)
Economy round-trip: 20,000-35,000 points
Southwest is hands-down the best value for Hawaii economy flights. Here’s why:
Why Southwest Wins
- No blackout dates: Any seat you can buy, you can book with points
- Revenue-based pricing: Points cost mirrors cash price
- Free changes: Cancel or change anytime, points go back to your account
- Two free checked bags: Even on award tickets
- Companion Pass eligible: Bring someone free!
How Many Points?
Southwest pricing varies by cash fare:
- Cheap fares: 15-20K one-way
- Average fares: 20-30K one-way
- Peak/holiday: 35-50K one-way
A good redemption is anything under 18K one-way from the West Coast.
Routes to Hawaii
Southwest flies to all major Hawaiian islands:
- Honolulu (HNL)
- Maui (OGG)
- Kona (KOA)
- Lihue, Kauai (LIH)
From: Oakland, San Jose, Sacramento, San Diego, Los Angeles, Phoenix, Las Vegas
Companion Pass Strategy
The ultimate Hawaii hack is the Southwest Companion Pass. Once you earn it:
- Designate one person as your companion
- They fly free (just pay ~$5.60 taxes) whenever you book
- Works on points AND cash bookings
- Valid through the calendar year you earn it + the following year
For Hawaii, this essentially cuts your points cost in half. A 30K round-trip becomes 15K per person.
Current offer: Southwest cards are offering Companion Passes as part of welcome bonuses through March 2026.
2. Hawaiian Airlines (Best Business Class)
Economy round-trip: 40,000 miles Business class round-trip: 80,000 miles (via Virgin Atlantic)
Hawaiian’s new 787 Dreamliner lie-flat business class is genuinely excellent — and there’s a trick to booking it cheap.
The Virgin Atlantic Sweet Spot
Hawaiian miles are hard to earn (no credit card transfer partners). But Virgin Atlantic Flying Club transfers 1:1 to Hawaiian Airlines, and you can book:
- Business class to Hawaii: 40,000 miles each way
- Round-trip: 80,000 miles + low taxes
Compare to Hawaiian’s own pricing of 80K+ each way, and you’re saving 50%+.
How to Book
- Search availability on HawaiianAirlines.com
- Transfer Chase, Amex, Capital One, or Citi points to Virgin Atlantic
- Call Virgin Atlantic to book (online booking sometimes works)
- Pay ~$50-100 in taxes
The Product
Hawaiian’s 787 business class features:
- Lie-flat seats in a 1-2-1 configuration
- Hawaiian-inspired cuisine and cocktails
- Premium amenity kits
- Overnight flights perfect for sleeping
This is the best business class product to Hawaii, and 80K round-trip is a steal.
3. United MileagePlus (Best Availability)
Economy round-trip: 45,000 miles (saver) Business/Polaris: 160,000 miles
United operates the most flights to Hawaii, making them the best choice when you need specific dates.
Award Pricing
| Class | One-Way | Round-Trip |
|---|---|---|
| Economy Saver | 22,500 | 45,000 |
| Economy Everyday | 35,000+ | 70,000+ |
| Business Saver | 80,000 | 160,000 |
Why Choose United?
- Multiple daily flights from hubs (SFO, LAX, DEN, ORD, IAH)
- No fuel surcharges on award tickets
- Partner flights bookable via United (Hawaiian, ANA connections)
- Excursionist Perk: Free stopover in another destination
Best Routes
United’s most frequent Hawaii routes:
- San Francisco → All islands (10+ daily flights)
- Los Angeles → Honolulu, Maui
- Denver → Honolulu
- Chicago → Honolulu
Tips for United Awards
- Book 330 days out for peak season
- Check for “saver” availability — costs half of “everyday”
- Transfer from Chase at 1:1
4. American AAdvantage
Economy round-trip: 45,000 miles Business round-trip: 160,000 miles
American’s Hawaii flights are solid, especially from their hubs.
Routes
- Los Angeles (LAX) → All islands
- Phoenix (PHX) → Honolulu, Maui
- Dallas (DFW) → Honolulu (seasonal)
Pricing
Same as United:
- Economy web special: 22,500 miles each way
- Standard economy: 32,500 miles each way
- Business: 80,000 miles each way
When American Makes Sense
- You have a stash of AAdvantage miles
- Flying from Phoenix or Dallas
- Premium cabin availability is better than United
5. Delta SkyMiles
Economy round-trip: 40,000-80,000+ miles Delta One: 150,000+ miles
Delta’s dynamic pricing makes Hawaii awards unpredictable, but deals exist.
The Good and Bad
Good:
- Decent economy availability at 20-25K one-way
- No fuel surcharges
- Comfortable 767 widebody on some routes
Bad:
- Prices swing wildly (same route can be 20K or 50K)
- Premium cabin redemptions rarely worth it
- Limited routes compared to United
Routes
- Los Angeles → Honolulu, Maui
- Seattle → Honolulu
- Salt Lake City → Honolulu (seasonal)
Strategy
- Be flexible on dates
- Search multiple departure cities
- Avoid peak holiday periods when prices spike
6. Alaska Mileage Plan
Economy round-trip: 40,000 miles First class round-trip: 100,000 miles
Alaska is a solid option, especially for West Coast flyers.
Routes
- Seattle → All islands
- Portland → Honolulu
- Los Angeles → Honolulu, Maui
- San Francisco → Honolulu (limited)
Award Chart
| Class | Each Way |
|---|---|
| Main Cabin Saver | 20,000 |
| Main Cabin | 25,000 |
| First Class Saver | 50,000 |
| First Class | 60,000 |
Alaska First Class
Alaska’s first class to Hawaii features:
- Recliner seats (not lie-flat)
- Pre-departure drinks
- Multi-course meals
- Solid for a 5-6 hour flight
Worth it at saver rates (50K each way), less so at standard pricing.
Strategy: How to Choose
If you want the best value:
Southwest — Points stretch furthest, especially with Companion Pass
If you want lie-flat business class:
Hawaiian via Virgin Atlantic — 80K round-trip for excellent product
If you need specific dates:
United — Most flights, best availability
If you’re flying from Phoenix/Dallas:
American — Direct flights from their hubs
If you’re flexible and patient:
Delta — Watch for 20K one-way flash deals
Booking Tips
When to Book
- 11 months out: Peak season (December, spring break, summer)
- 3-6 months out: Shoulder seasons often have good availability
- Last minute: Southwest releases inventory as flights approach
Best Time to Visit Hawaii
- Cheapest awards: September-early December (excluding Thanksgiving)
- Best weather: April-May, September-October
- Avoid: Christmas/New Year, spring break, summer peak
Which Island?
| Island | Best For |
|---|---|
| Oahu | First-timers, nightlife, history (Pearl Harbor) |
| Maui | Honeymoons, beaches, Road to Hana |
| Big Island | Volcanoes, adventure, seclusion |
| Kauai | Nature, hiking, dramatic scenery |
Current Deals & Offers
- Southwest: Companion Pass in welcome bonuses through March 2026
- Chase: Transfer bonuses occasionally available to United, Hyatt (for hotels)
- Hawaiian: Check Virgin Atlantic Promo Rewards for discounted awards
Sample Itinerary: Family of 4 to Maui
Using Southwest + Companion Pass:
- Parent 1: 30,000 points round-trip
- Parent 1’s Companion: FREE (just $11.20 taxes)
- Parent 2: 30,000 points round-trip
- Parent 2’s Companion: FREE (just $11.20 taxes)
Total: 60,000 Southwest points + $22.40
For a family of 4, that’s effectively 15,000 points per person to Hawaii. Try beating that value anywhere else!
Final Thoughts
Hawaii is one of the most rewarding uses of points and miles. The key is matching your program to your priorities:
- Value seekers: Southwest (especially with Companion Pass)
- Comfort seekers: Hawaiian 787 business class via Virgin Atlantic
- Flexibility seekers: United MileagePlus
Start by checking what points you already have, then work backward to find the best redemption. And remember — the best award is the one that gets you to the beach!
Planning a Hawaii trip? Share your redemption in the comments!
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