Hawaii 🏝️ in $270s-$290s RT

This deal is a tale of two islands, and you've got a tough choice ahead of you.

Don't get us wrong—Hawaii is Hawaii, and both Maui and Kauai are a total dream. But they're two different flavors of paradise.

If you close your eyes and think of "Hawaii," you're probably picturing Maui. It's got the waterfalls, it's got the snorkeling, it's got the beaches (boy, does it ever have the beaches). It's also the best place around to do a little surfing, if that's on your bucket list.

Kauai is like Maui's quieter cousin. The beaches are a little less spectacular, but they're a lot less crowded, so you'll have even more room to relax and sip mai tais in the sun. Kauai also holds the edge for hikers, offering stunning views that... well, just see for yourself.

Then again, you can always skip the hard choice and just visit both :-)

P.S. Hawaii is a beautiful place to visit, but overtourism can be a burden on the people who live there. Check out the Sustainable Tourism Association of Hawai'i site for some tips on minimizing your footprint.

Taking off ✈️

Tip Published: Apr 11, 2025

To:

  • Kahului (OGG) - $278
  • Kauai (LIH) - $298
From:

  • San Diego (SAN)
Flight Details

Travel Dates

Login or Register to view

Airline

Login or Register to view

Standard Fare

$500 (non-stop, peak summer)

Bags & Fees

Login or Register to view

Book By

Login or Register to view

Flight Notes

Login or Register to view

How to Book

    This is a Premium deal for Jack's Flight Club members only. For step by step instructions on how to book it you'll need to login or upgrade to Premium membership.