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3 Very Easy Ways to Book Free Flights to Your Cruise Port (or Any US City!) With Chase Ultimate Rewards Points

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Cruises are a wonderful cost-effective way to travel.  I’ve been on 5 and my parents have been on over 30!  On a cruise you can relax and eat too much, or explore a new place and eat too much… all without the stress of doing all the planning yourself.  So why should the flight to the port departure city be difficult and expensive?  It shouldn’t!

Before you just accept the Cruise and Airfare package from the cruise line or your travel agent, check out how to book free flights with Chase Ultimate Rewards points! 

To do this, you’ll need at least one of the following terrific travel credit cards: Chase Sapphire Preferred® Card, (the best card for beginners to using travel points instead of money!  I have this card and love it!), Chase Sapphire Reserve® (many on our team have this one), or Ink Business Preferred℠ Credit Card (this card has the biggest Chase Ultimate Rewards points sign-up bonus!)

There are lots of ways to fly free with Chase Ultimate Rewards points, but here I’ll cover the 3 simplest — and there are no blackout dates with any of them!

I Used Chase Ultimate Rewards Points for a Free Flight to New York City to Meet My Family for Our Cruise to the Bahamas on the Norwegian Breakaway.  The Water Was Pretty Warm in February!  Not as Warm as the Kiddie Pool on the Ship Though.

I’ll start with how to book any airline you want.  But if you live near an airport served by Southwest or JetBlue, you just may want to read further to see how to get an even better deal!

1.   Book Any Flight You Want With Chase Ultimate Rewards Points at a Serious Discount

The Chase Travel Portal.  This is the absolute easiest way to use your Chase Ultimate Rewards points for flights.  It’s just like Expedia and the prices are the same.  Book a flight here with points from your Chase Sapphire Preferred or Chase Ink Business Preferred and you’ll get a 25% discount!

For example, your 50,000 Chase Ultimate Rewards points are worth $625 for any flight you want.  (Otherwise your 50,000 points are worth $500 cash.  I love cash, sure, but travel is better.  Money CAN buy happiness.  It’s called going on a cruise!  I saw that on a t-shirt once.)

If you have the Chase Sapphire Reserve, it’s even better.  Using this premium credit card, each point is worth 1.5 cents.  So your 50,000 points are worth $750 for any flight you buy on the site.

This Is the Chase Travel Portal.  It Automatically Tells You What Your Points Are Worth!  With the Chase Sapphire Reserve, Each Point Is Worth 1.5 Cents.  So 15,000 Points Gets You $225 Worth of Flights!  That’s a Great Deal, Because Ordinarily 15,000 Chase Points Are Worth $150.

Now let’s go from the super easy method to the nearly-as-easy-but-more-valuable way…

2.   Transfer Your Chase Ultimate Rewards Points to Fly on Southwest

Note to folks with the Chase Sapphire Reserve:  Southwest points are worth roughly 1.5 cents each.  So if you have the Chase Sapphire Reserve, you might be better off buying your Southwest flights through the Chase portal rather than transferring your points. The “catch” is Southwest refuses to put their flights online anywhere except Southwest.com.  No worries.  Just look up the flight you want on Southwest.com, then call the nice folks at Chase travel to book that exact flight with your Chase points: 866-951-6592.

If you have the Chase Sapphire Preferred or Chase Ink Business Preferred, transferring your points to Southwest is a great move.  And it’s so simple.  With a couple of clicks you can turn your Chase points into Southwest points.  It’s magical, much like the midnight chocolate crepe station on the ship.

What I do is first is move all the Chase points from my no annual fee  Chase Freedom® over to my Chase Sapphire Preferred.  Because then I’m allowed to send my points to Southwest.

Then all you do is log into your Chase.com account and click the big “Transfer to Travel Partners” button:

After you move your Chase points into Southwest’s program, you can go ahead to Southwest.com to book!  That’s it!

Southwest doesn’t play any games, so if the flight is for sale, you can buy it with points.

What’s more… on Southwest you always get 2 free checked bags per passenger!  That’s a HUGE savings when you’re headed out to a cruise.  Bring all the sun hats, big bottles of lotions, shoes, and outfits you want!  Personally, I bring my skinny jeans for Day 1, baggy jeans for Day 2, and by Day 7 of the buffet I’m in a MuuMuu with flip-flops headed over to the midnight chocolate crepes station.

I Snapped This Photo After My Last Cruise.  Sure, You COULD Squeak by With a Carry-on.  But What Fun Is That?!  Bring All Your Favorite Outfits and Full-Size Shampoos When You Get 2 Free Checked Bags per Passenger on Southwest!

Check your local airports to see if Southwest flies out.  But I can tell you right now that Southwest flies into these major cruise port departure cities plus others!

3.   Transfer Your Chase Ultimate Rewards Points to JetBlue

Again, if you have the Chase Sapphire Reserve, you might be better off booking with Chase Ultimate Rewards points through the Chase travel portal.  But for folks like me with the Chase Sapphire Preferred or Chase Ink Business Preferred, transferring to JetBlue is the better deal.

Here I Am as We Docked in the Bahamas!  (I Edited Out the Chocolate Stains of Glory on My Shirt.)

JetBlue has no blackout dates.  So if there are still seats on the plane, you can book with points instead of money!  I’m a big fan of JetBlue.

I don’t like that they charge for checked luggage, but everyone does these days, except for Southwest.

Being a person of height, I’m thankful for the extra legroom in the regular economy seats.  They have live satellite TV which is great for watching sports, news, movies, etc.  And they’ve got great snacks. 🙂

In Addition to Satellite Radio, on JetBlue You Also Get Live TV!  But Most of All, I Appreciate the Comfortable Seats and Legroom.  And on the Way Back Home I Appreciate How Much Those Seatbelts Loosen

JetBlue flies to these major cruise port cities and more:

If you really want to treat yourself to luxury on the way to your cruise, consider booking JetBlue’s Business Class seat that they call Mint.

JetBlue “Mint” Business Class Is Often a Great Deal With Chase Ultimate Rewards Points!  You Can Sleep in the Bed and Your Checked Bags Are First to Come Out!

This just might be the best domestic Business Class experience in the US!  JetBlue Business Class is available on certain routes to cruise ports such as:

From Boston to these cruise port cities:

Escape Los Angeles and San Francisco to Fort Lauderdale (to get to Port Everglades and Port of Miami)

Get to New York – JFK in style from:

Bonus Section: Earn Chase Ultimate Rewards Points Booking Your Cruise!

Whether you book your cruise with the cruise line, a travel agent, or on a site like Expedia, you’ll earn 2X Chase points when you pay with your Chase Sapphire Preferred.

And you’ll earn 3X points with your Chase Sapphire Reserve or Chase Ink Business Preferred.  (Note: See the application page for the Ink Business Preferred points-earning maximum, but it’s really high.)

So each time you use one of these credit cards to book a cruise, you’re earning points towards your next free flight!

Bottom Line

If Southwest or JetBlue serve one of your home airports, consider transferring your Chase Ultimate Rewards points to those loyalty programs to book comfortable flights.

Or you’ve always got the option to book any flight you want at a significant discount with no blackout dates in the Chase Travel portal.

To book discounted flights like this with Chase Ultimate Rewards points, you’ll need one of these great travel credit cards: Chase Sapphire Preferred, Chase Sapphire Reserve, or Chase Ink Business Preferred.  Everyone on our team including me has either the Chase Sapphire Preferred or Chase Sapphire Reserve.

If you have a small business (you can apply with your social security number if you don’t have a tax ID) I highly recommend the Chase Ink Business Preferred because it has the highest sign-up bonus.

But really, you can’t go wrong with any one of these 3 powerful cards.  They’re nearly as powerful as cruise ship toilets!  But that’s another story.  Lots of our regular readers and folks on our team have the Chase Ink Business Preferred AND either the Chase Sapphire Reserve or Chase Sapphire Preferred.

I also feed my Chase Sapphire Preferred with Chase Ultimate Rewards points that I earn from my 2 no annual fee cards: Chase Freedom and Ink Business Cash℠ Credit Card.  Because then I can use all my Chase points for cheap flights.

In case it wasn’t obvious, Chase Ultimate Rewards points are our favorite type of travel points. 🙂  Because you can use them for fancy international First Class flights or for simple quick discounts to US cities to see family, friends, or to get to your cruise!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)