Hawaii Round Trip from $541: Houston, Chicago, and Newark!

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My current favorite family vacation destination is Hawaii (in fact, if I wasn’t due to have a baby any day, we would be there on a trip right now that I had to cancel!).  The biggest downside to Hawaii, aside from it being pretty far for some of us, is that it is usually not cheap to get there or stay there.  This is where miles and points often come into play, but occasionally there are airline “fare wars” that make purchased tickets temporarily drop into the realm of reasonable prices from select cities.  These deals never last very long, so you must move quickly when they appear.

The Garden Isle of Kauai

The Garden Isle of Kauai

Via The Flight Deal, if you act quickly you can get round trip tickets to Hawaii on American/US Airways from $541 from the following cities:

  • Newark [EWR]
  • Chicago [ORD]
  • Houston [IAH]

You can fly to the following Hawaiian cities:

  • Honolulu [HNL]
  • Maui [OGG]
  • Kauai [LIH]
  • Kona [KOA]

Prices on these routes are routinely several hundred dollars higher than this, so don’t wait if you want in.  With American Airlines you can put flights on hold for 24 hours while you decide if you want to keep them, so at the very least do that if you are interested in these prices

These prices are valid on select dates from mid-August – May, 2016.  If you happen to be eying flights from Houston, I even saw spring break available at these prices!  As shown below I used ITA Matrix to use a calendar search for the lowest fares, and then went to American Airlines to actually price out the tickets and purchase or put on hold the flights that look best for you.

Cheap Flights to Hawaii

Congrats if you are able to get in on one of these discounted fares to one of my favorite spots in the world!

Sunset in Kauai

Sunset in Kauai

If this has caused you to start planning a trip to Hawaii, then check out my video with the Travel Channel on how to Save Big on a Trip to Hawaii and lots of hotel reviews I have written on points-friendly properties in Hawaii here.

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. Hawaii is my favorite vacation destination as well. Our family has visited for the past 5 summers! When planning our summer vacation others often inquire about why we don’t visit a new tropical destination. We can’t describe why Hawaii has become such a special place for our family but I just feel invigorated and at peace while I’m there. We cherish our time here and can’t wait to return next summer. We have been extremely fortunate with finding a window of time right when our kiddos (3 of them) begin summer break when flights and lodging are less expensive. We have considered visiting at other times of the year but can’t justify paying more when we know we will save if we visit at our usual time. Good luck with the baby and hopefully you will get back to the Aloha state real soon.

  2. Am I too late to plan a trip in November? I still don’t know from where I start my journey (could be ORD, SFO or SEA). I plan to use AA miles though. I don’t have hotel points. Can I bank on Airbnb or VRBO at Hawaii? I do have Arrival+.

    • Sam, it’s not too late to plan a trip for tomorrow depending on your situation, so November can work. You can certainly rent a house or similar there if you wish – can be a really good deal actually. Award availability can be hit or miss, but as long as you aren’t talking about Thanksgiving week hopefully award availability will be on your side!

  3. Just got back from my honeymoon in Maui in June and I already want to plan a trip back! It’s a magical place!!

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