Fly in October & December-May to Hawaii in $420s-$570s RT with Southwest, American and more.

Jack's Flight Club

Premium Deal Alert: 18 July 2022

You can't hold on to a midweek slump for long when you've got a Hawaii trip to plan :-)

The best news is that most these fares cover dates in late 2022 and early 2023, the most in-demand time to visit Hawaii. If you're booking with American you'll get some Main Cabin extras like seat selection included. And you lucky Chicagoans get your bags included with Southwest.

Click on your destination city below to search availability and fares on Google Flights or Southwest. Use their calendar tool to find the best travel dates for your route by locating the dates with the lowest fares (highlighted in green on Google Flights). 

 

Here's the deal

Routes

Round trips from New York (JFK):

Kahului (OGG) - $466-$488 (December-May)

Kailua-Kona (KOA) - $514 (January-May)

Kauai (LIH) - $514 (January-May)

Round trips from Orlando (MCO):

Kauai (LIH) - $569 (January-February)

Round trips from Chicago (MDW):

Kahului (OGG) - $425-$433 (October)

Details

Travel Dates

October & December 2022 - May 2023 (varies by route)

Airline

Southwest Airlines, American Airlines, Hawaiian Airlines, Delta Air Lines

Standard Fare

$600-$700

Bags & Fees

Checked bag is $60 RT or free (x2) with Southwest. Seat selection varies by airline.

Book by

This deal may only last a day or two.

Dedicated to the Deal: Our only incentive is helping you land a great deal, so we don't accept any sponsored links or advertising content in our deal alerts.

Essential travel info:

Check your airline for their flexibility policy. Be aware of Basic Economy tickets, as they often have limited flexibility if you need to change your trip later on.

Questions about Covid? Check out our FAQ!

How to book it

Step1

We recommend Google Flights to find this deal because it has an easy-to-use calendar tool to browse dates and fares. See an example itinerary by pressing the blue button below or click on your desired destination above.

Select one of the date boxes to expand the calendar view and see fares for each departure date. The fares shown will update if you pick a longer or shorter trip - trying different lengths can reveal more options.

Once you find dates at the deal price we listed, get a link to book directly with the airline by selecting the outbound and return flights.

Note: To find the Southwest deal fares, you'll need to use their Low Fare Calendar.

Type in your departure, destination and travel month and press β€˜Search’. On the next page, you’ll see the cheapest days to fly on a calendar view.

Once you’ve selected dates, complete your booking with Southwest.

Find on Google Flights

 

Example Itinerary