HURRY! Southwest Adds New Hawaii Routes From Just $29 Interisland Or $99 To/From The Mainland Each Way!

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Southwest is adding several new Hawaii routes in January. You can view all the lowest fares via the low fare calendar links below, but each flight only has a limited number of seats on sale!

All fares include 2 free checked bags and free changes!

These flights are also on sale with points and Chase points transfer instantly to Southwest at a 1:1 ratio.

Chase premium cards with transferable points include:

  • Chase Sapphire Reserve®
    • $450 annual fee, $300 in annual travel credit, 50K points signup bonus, earn 3 points per dollar on dining/travel, 50% bonus value on using points for paid travel redemptions, Global Entry/Pre-check, Priority Pass lounge access.
  • Chase Chase Sapphire Preferred® Card® Card
    • $95 annual fee waived for first year, 50K points signup bonus, earn 2 points per dollar on dining/travel, 25% bonus value on using points for paid travel redemptions.
  • Chase Ink Business Preferred
    • $95 annual fee, 80K points signup bonus, earn 3 points per dollar on select business spending and travel, 25% bonus value on using points for paid travel redemptions.

Chase no annual fee cards with transferable points if you, a spouse, or an additional user have one of the premium cards above include:

You can also earn Southwest points on Southwest branded cards:

Want to read more about Hawaii?

My love of Hawaii began 13 years ago when I posted and grabbed a deal paying just $87 for airfare and hotel.  Since then I’ve been lucky enough to spend several months between the stunning islands, which each offer a unique and wonderful experience.  You can’t go wrong with any of them, there are just 2 things is to be careful of.

Always a good day in Maui #MauiNoKaOi

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1. Don’t get stuck in Honolulu. I’ve heard from too many people who spent an entire week and never left the city limits.  That’s just a shame, they may as well have gone to Miami Beach.  While I prefer The Big Island, Kauai, and Maui to Oahu, there is still plenty to see and experience on Oahu as long as you leave Honolulu behind.
2. Don’t try to “do” several islands in a week. If you just have 4-7 days of vacation then you should stick to one island. There will be plenty to do to keep you busy and it will allow for some time to relax. There’s no need to add the stress of interisland travel just for the sake of “doing” another island. With 9 days or more to play with, it does make sense to experience more than 1 island.

As for which island is best, read on and decide for yourself!  If you ask 5 people you’ll probably get 6 different answers 😀

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#Paradise #Kauai @grandhyattkauai

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DansMeals: Hawaii For The Kosher Traveler:

Trip reports and posts on Hawaii:

DDF forum threads:




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31 Comments On "HURRY! Southwest Adds New Hawaii Routes From Just $29 Interisland Or $99 To/From The Mainland Each Way!"

All opinions expressed below are user generated and the opinions aren’t provided, reviewed or endorsed by any advertiser or DansDeals.


which california airport is best to fly out of? coming from Chicago anyway.


Just booked two provisional trips in February, with partial overlap to school vacation. All that’s left is telling DW about it…. thanks, Dan!


very few $99 one way tickets using any of the above 5 links for Jan


How’s the weather there in Jan? is it worth going for the first time or wait until a more optimal season?

Mark Davis

In January, it’s still going to be 80 degrees.


Maui will probably have rain, but not all day.

Walter W Stumpf Jr

I didn’t find anything at these low prices:(

Anyone have any luck?


can use 7.5K AA for interisland flight (free luggage) or $39 for southwest. Which better?


all these fares are for people who don’t have kids in school. $99 are mostly on Tuesday.


Are these tickets refundable?


Is there any way to use southwest to book from NY/NJ or Philadelphia (obviously it will cost more)? I just get “unavailable” on all dates?


I am only getting $99 both ways not roundtrip and with fees its well over $200 – any idea?



It goes a long way


To make any sense

This comment must be read backwards


Have 9-10 days for trip with arrival in OGG on Sunday and keeping 2 days Shabbos. Will be flying out of KOA on Tues (likely), so should I switch over from Maui to Big Island on Sun or Mon afternoon?


You hold of the opinion of keeping 2 shabbos days in hawaii. Good luck!

Gordon L

We enjoyed several islands in a week by taking the cruise. It was great for our first time and when we return, we know where we want to go. On the cruise, you hang up your clothes one time and then enjoy the sites.


They have a route from BWI to HNL and OGG on one ticket, but no returns


Southwest Air? I’ll pass. My experiences on Spirit have been better than SW on my last few flights. Boarding zones A,B, and c can line up like a Walmart checkout- I’ll be flying elsewhere.


Is there anyway whatsoever to get Southwest to reinstate recently expired points?


Can’t find any of those fares today!!!