Chicago to Maui Package Deal

Fly from Chicago to Maui on Nov 1 – 8th. 7 night package deal from $2465 per couple!

outrigger royal kahana maui


Includes round-trip airfare from San Diego, 7 nights in an ocean-view studio condo at Outrigger’s Royal Kahana and a compact rental car.


Rental car  taxes estimated at $76 and a condo cleaning fee $95+ tax.

About the Outrigger Royal Kahana

Nestled between Kapalua and Ka’anapali, these condos include a kitchen. Bordering a beautiful beach, guests enjoy a relaxing oceanfront swimming pool and a fitness center just steps away from a selection of unique shopping and dining.


Your flights are on United combined with Hawaiian Airlines with a change a planes in San Francisco.  It’s an early morning flight on the departure and an overnight flight on the return.

How to Book:

Reserve this package here via my secure online form. Reference Deal 193 when filling out the form.

Call me if you have any questions.  877-34-TRIPS

Other room category upgrades are also available.

This requires a down payment of $1529.98 person. Final payment is due on Sep 10.

Make sure your names and birthdays are submitted on the form exactly as they appear on your driver’s license.

Prices are subject to change at any time.

We can help you arrange your excursions, luau and other activities.

Optional Vacation Insurance

If you’d like optional cancel for any reason vacation insurance, it is an additional $139.99 per person. Without the insurance, the package is non-refundable. Please specify on the booking form whether you’d like the insurance or not.

Why Book With A Travel Agent?

When you book with us, we are your trusted travel agents. We know the properties we sell and we create customized itineraries for you with our favorite suggestions of what to do and where to eat, etc.  If you have any questions, we are real people that can help you with anything you need and have your back in case of any issues. We have relationships with the managers at the resorts we sell.

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Welcome to Hawaii Airfare Deals

Hello, I’m Krista Mayne and I’m a Hawaii obsessed travel agent.  My aim for this website is to get you to Hawaii as often as I can.  Check back often for the best deals.

Airfare deals change often, so if you see something you love, act on it quickly.

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