Deal Alert: Portland to Osaka for $574 Roundtrip

Another day, another deal! And today’s is a goooood one. So grab your pen and paper, because you’re going to want to take notes. Right now, you can fly roundtrip from Portland (PDX) to Osaka (KIX) for just $574—a solid drop from the usual $644+ fare.

If you’ve been waiting for an excuse to visit Osaka, this is it. Let’s get you there! (And keep in mind, this wasn’t a specific “deal drop,” but you can easily find it by searching availability in your Daily Drop Pro account from PDX to KIX).

Travel Deets

Airline: Hawaiian Airlines
Route: PDX → KIX (with a layover in Honolulu)
Seat Class: Economy
Best Deal Dates: Select dates in August, September, October, and beyond

Why This Deal Is Amazing

Flights from Portland to Osaka usually run between $644 and $831 roundtrip, with anything under $600 considered a solid deal. At $574, this is one of the lowest fares we’ve seen recently.

For context, the last time we saw a deal this good was $575 just a few weeks ago, and fares have hovered around $600+ in recent months.

Want to book with points? Here’s what it would cost:

Chase Ultimate Rewards: ~38,267 points
Amex Membership Rewards: ~57,400 points
Capital One Miles: ~57,400 miles

If you have HawaiianMiles, check award availability—you might find a redemption that beats these numbers.

Where to Stay in Osaka

Osaka is packed with amazing hotel options, whether you want something boujee, mid-range, or budget-friendly. Here are some top picks:

Luxury Stay: Conrad Osaka

If you want breathtaking city views and five-star service, Conrad Osaka is a fantastic choice.

Cash Price: ~$400 per night
Points: ~95,000 Hilton Honors points per night

Mid-Range Stay: Marriott Osaka Miyako Hotel

A sleek, modern hotel with great amenities and easy access to the city’s top spots.

Cash Price: ~$250 per night
Points: ~40,000-50,000 Marriott Bonvoy points per night

Budget Stay: Hotel The Flag Shinsaibashi

A stylish boutique hotel with a prime location near Dotonbori’s lively streets.

Cash Price: ~$120 per night
Points: Not bookable with major loyalty programs, but a great value for cash stays.

How to Book

Flights: Search this deal on Daily Drop Pro (duhhhh 🙂), Google Flights, or Hawaiian Airlines’ website. If using points, check Chase, Amex, or Capital One travel portals.

Hotels: Book through Hilton, Marriott, or Expedia for the best rates and elite perks (but watch out for lost benefits if booking through OTAs).

Pro Tip

Osaka is the ultimate foodie city, so don’t leave without trying takoyaki, okonomiyaki, and kushikatsu (and thank me later!).

If you have extra time, hop on the train to Kyoto for a day trip to see some historic temples or take the bullet train to Tokyo for an extended trip. With flights this cheap, why not make it a whole tour?

Now go book before these fares disappear! ✈️ For real though, this one is insane.