Roundtrip Airfare to Hawaii As Low As $315

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Head to Hawaii for an Epic Vacation! 🌺

Several travel booking sites such as ExpediaPriceline and Orbitz are offering up HOT deals on travel to Hawaii from various US cities with travel dates throughout 2018 and in to January 2019. As one idea, I spotted tickets from San Diego, CA to Maui, HI for as low as $315 roundtrip!

Hip Tip: To get the best prices, head here and use Google Flight Search to find the lowest priced days for travel. Just enter your to/from destinations and click on the calendar icon to select your flight dates. The prices listed in green are the lowest prices. Make note of those dates, but don’t purchase tickets on Google. Instead, head over to ExpediaPriceline or Orbitz to book your flights on those low fare days.

Check out these deals I spotted:
  • Portland, OR to Maui, HI $373 Roundtrip
  • San Diego, CA to Maui, HI $315 Roundtrip
  • San Jose to Kahului, HI $397 Roundtrip
  • Denver, CO to Kahului, HI $467 Roundtrip
  • Phoenix, AZ to Kahului, HI $327 Roundtrip
Live on the East Coast? I spotted these deals…
  • Ft. Lauderdale, FL to Kahului, HI $432 Roundtrip
  • Boston to Kahului, HI $374 Roundtrip
  • Richmond, VA to Kahului, HI $697 Roundtrip
Join The Discussion

Comments 51

  1. Tracey

    Maybe I’ll go to Hawaii for summer vacation.

    • Amber (Hip2Save Sidekick)

      What a fun summer vacation Tracey! 😉

      • Ila

        I am enjoying my grandchildren and watching t h email grow.


      Those prices are nice that is my dream trip Hawaii

  2. Donna

    This is just an amazing price!

    • Craig

      Yeah, if you live on the West Coast. 🙁

  3. Jennifer

    I can’t find the Ft. myers to Hawaii trip for $ is showing $772 as the cheapest for me. Do you know what airline that was?

    • Kellie

      I think they meant to put Ft Lauderdale instead of Ft Myers. Try FLL as the airport.

      • Amber (Hip2Save Sidekick)

        Thanks Kellie! That has been updated!

    • Amber (Hip2Save Sidekick)

      Sorry for the confusion! Be sure to check “Ft. Lauderdale, FL to Kahului, HI”. That has now been updated!

  4. Emily

    Has anyone heard about when Southwest will fly to Hawaii??

    • Ang

      My brother flies for Southwest and they will be adding flights to Hawaii this year I believe.

    • Rená

      I don’t know either, but I’ve been checking for an update monthly! Ready to use that companion pass.

  5. Andrew Falkowski

    If you book through Momondo it’s even less. Especially with Star Alliance Carriers (United, Air Canada, Lufthansa). I just booked round trip tickets to Italy from Minneapolis last week for $407 per person in September/October.

    • alesia

      Thanks Andrew. I’ve never used momondo before but I’m downloading the app now.

    • 2009baby

      I just downloaded the app. It is really nice! I was wondering if anybody know any app similar to this for hotels? TIA

  6. ShopHopper

    American Airlines and Alaskan Airlines have some of the cheapest flights to Maui if you are travelling from the Midwest – connecting flights to Phoenix AZ or Dallas TX with short flight times and quick connections. You will often find round trip pricing under $500.

  7. Denise Lemke

    I only fly to Hawaii from the west coast on Alaska AIr because I have a companion ticket so I get one RT for $129 with taxes so we are flying on May 31 for $587 for two people- BUT….as much I hate flying United….. I did see RT on United from San Fran to Maui for $397 RT – that is an amazing price…..San Fran is typically never cheaper than Oakland or San Jose and it is right now…. Look in May/June…

    • Divya

      Me too don’t prefer United. We travelled to India with my infant and also reserved an bassinet n also confirmed just before boarding. While in the flight their either bassinets are fitting into the hook. While asking if we can move to a different bassinet head seat they refused and were very rude to us. Entire 15hrs flight I wasn’t able to sleep a bit. It was really an horrible journey for me and my lil one. In addition I had my 5year old too. It was so exhausting.

  8. Kate

    wow boston to hawaii under $400, wish I could make that happen!

  9. Emily

    What are the dates to find airfare that cheap from Boston? The cheapest I can find is $572.00

    • jeanette

      the only date i found this low was from oct. 24 to oct. 30, it came out to $374 roundtrip from boston, i looked on google flights

      • Emily

        Thank you Jeanette!

    • kate

      I saw early and late April too for under $400 from Boston!

  10. T

    Thank you for the tip about Google Flight Search , didn’t know about it

    • Collin (Mrs. Hip)

      You’re very welcome! SO glad to help you grab the best deal!

  11. laura fuller

    We live in Portland and are going to Hawaii July 31. I’ve been fiddling on these sites and I don’t see any tix for $300. We are doing a multi city trip. Pdx to Honolulu, then Honolulu to Maui, Maui back to Pdx.

    • Lynn

      Skiplagged is also a great place to look for flights. It helped me find a Pdx to Hnl flight last year with United (the worst! but tolerable) in July for $180 each way.

  12. Amymae1100

    Anything out of DFW or Bush? I need a vacation from my littles, LOL!

  13. je

    I use to do my searches. For me, it’s a bit more straightforward than Expedia, Travelocity, etc. I use it as a search tool only though, so no experience booking through them. I like to book directly through the airline and hotel. With that said, for anyone from Seattle wanting to go to Hawaii, there are RT fares on United for $300+. We’re going to Kauai in August and got RT for $373.

    • riss

      I booked with kayak in the past and have had no problems at all. Even Travelocity, expedia, orbitz, cheaptickets and priceline, no problems so far (knock on wood!)

    • Esme

      What are the dates from Seattle I live on the east side of Washington looking for take off from Seattle or Spokane

      • je

        Esme… we’re going end of August. If you search through Kayak, they usually have little green dots next to the dates of the cheapest flights. You won’t know the exact price until you search, but that gives you an idea of what dates have the lowest fares.

  14. Kri

    I can’t find how to get the green dates – it is making me pick specific dates and I just want to browse the calendar to find the cheapest days to travel – how can I do this?

    • Monique

      There is an app called hopper that shows green/yellow/red dates to travel for flights

  15. Madelyn

    BAAHHAAA! Just booked four flights for June to the tune of $4100! Murphys law!
    Thanks you guys, though, I feel a little better considering we can’t control the dates AND we are headed to the Big Island. So cheap flights are harder to come by – but these are AWESOME – like y’all!

    • Holly (Hip2Save Sidekick)

      Aww, bummer! I hope you enjoy your trip!

    • mamahosh

      Depending on the airline, you may be able to get a price adjustment on your tickets if the price drops before you travel. I purchased 3 tickets to Portland on Alaska Airlines back in November and within a few weeks, the price had dropped almost $100 each. With just a few clicks on Alaska Airlines website, I was able to get refunded almost $300!


    My people!

    My family is still there. I’d love to go visit but the normal fare is WAY out of budget for a household of four! It would have been around $5K for us to go in December.

  17. Ila

    Enjoy your summer vacations.

  18. Ashley

    We booked a round trip to Hawaii ( Monday-Monday) in September for 445$ round trip per person last month! Can’t wait!

    • Jackie

      That sounds like a great deal! What website do you use?

  19. Moni B.

    Thank u (mahalo) for the heads up! I’m actually hoping to fly OUT of Hawaii this year for several short vacays. My situation is different from most peeps…I live on Oahu and need to get “off the rock”. 😀 Hoping to find deals on my outbounds & then take advantage of these deals to return home!

    • Krisi

      Can we trade lives for a while 😜
      I live in southeast Texas if you’ve ever wanted to visit Houston I’ll trade houses for a week (or forever)

  20. Shannon

    Why nothing out of dfw or kc??? I looove Hawaii. It’s the best place ever!

  21. Gloria

    Hi all ! Since we are in the subject of flying, my husband and I would like to visit my son in SanDiego in June. From BWI – SanDiego . Does anyone have any idea how we can get a good deal on round trip tickets for two. I miss my son so much , I have to get a good price or we can’t go 🙁 . Please help TY

    • Stephanie

      Sign up the for the southwest credit card and get the bonus….I can refer you…..You guys should be able to fly free! I can send you a link if you want more info on it…

    • Gloria

      Yes please

  22. Susie

    Thank you so much!! Booked our tickets from Columbus,Ohio to Maui for 444.00 per person. I paid 750.00 in 1999 and 750.00 in 2010.

  23. Megan

    Never any good flights leaving Des Moines… and the coldest part of country needs to be the cheapest 🤷‍♀️

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