A Daughter’s Dream: Wicked on Broadway, JAX to NYC

A Daughter’s Dream: Wicked on Broadway, JAX to NYC


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Trip Information

PointsAway reader Brian wants to take his wife and daughter from Jacksonville to New York City, on a Friday to Sunday sometime during October, to see Wicked on Broadway.

Current Program Status

Brian is an American Express member, and recently used most of his Membership Rewards® in order to book a trip to Europe and for a roundtrip flight to San Francisco.

His current point balance is around 3,000. He does not currently hold any airline or hotel-specific cards or memberships with significant point balances.

Our Take

This sounds like the type of trip a girl will never forget. Since its debut in 2003, Wicked has remained one of the world’s most popular Broadway productions. While the show now tours across the country and was even in Jacksonville last year, I’m sure nothing beats seeing the real thing in New York City.

NYC can be a challenging destination for points users. While flights are readily available and often fairly cheap, most hotel chains add a category or two to what a property might earn in another city due simply to its location. [quote_right]NYC provides a great opportunity to score massive value from free night offers, making for an itinerary fit for a princess.[/quote_right]This makes it difficult to use points in a way that doesn’t feel wasteful for most chains. The listed rates are often quite steep, as well. Properties with basic amenities cost several hundred dollars per night on average to be in a centrally located part of town.

Far from being bad news, however, the economics of lodging in NYC provides a great opportunity to score massive value from free night offers, the type only possible in such a world capital. This provides a great opportunity to make an itinerary that’s not simply far cheaper than cash alone could provide, but one that’s fit for a princess and ties the whole trip together into an unforgettable experience.

How to Fly

Two airlines provide the best value from JAX to the greater New York City area, depending on which weekend in October is selected.

Southwest Airlines

Southwest offers the most points-effective roundtrip flight, from October 11th to October 13th, at just 35,457 points & $30.00 for all three roundtrip tickets.

Southwest’s program is one of our favorites because they offer a revenue-based points program. For flights where Wanna Get Away® fares are available, it takes just 60 points per dollar for redemptions. In other words, you get about 1.67 cents of value per point, which is pretty fair for a domestic flight. This escalates to 100 points per dollar on Anytime tickets and 120 points per dollar for Business Select®, so Wanna Get Away® fares are definitely the best opportunity to redeem miles with Southwest.

There are two departure possibilities that make sense on October 11th. The one for the least amount of miles requires a plane change and doesn’t arrive until late Friday evening, so in this case it may be worth springing the extra points for the earlier, shorter itinerary without a plane change.

One return flight offers outstanding points value at 5,040 per person. Unfortunately, the next cheapest return flight later in the day is 12,120 points per passenger, or more than double the one leaving early on Sunday morning with a stop in Midway.

At just 35,457 points for the whole trip, or a few thousand more if Brian wants to take an earlier flight to New York, all of the flights can be easily covered by the 50,000 point sign-up bonus offered by the Southwest Rapid Rewards Plus® Credit Card. This card has a $69 annual fee that is not waived for the first year, and pays out its bonus after $2,000 in spending in the first 3 months. All the details are available on our Sign-Up Links page.

If Brian really wants the family to have a full Sunday in the city before returning home, the best bet is to take the 9:20PM flight on JetBlue out of JFK, returning to JAX at 11:54PM. That flight costs 10,400 TrueBlue points + $2.50, or $151 per ticket according to Kayak. More on TrueBlue points soon.

Southwest and JetBlue reward tickets are booked as one-way trips, so it’s possible to mix points redemptions with cash fares or even other airlines effectively. Not all airlines work this way; Delta SkyMiles, for example, which charges one-way trips at the full roundtrip points amount!


Flying JetBlue for the entire trip is the other possibility, from October 18th to October 20th at just 37,800 points & $15.00 for all three roundtrip tickets.

JetBlue offers direct service to and from Jacksonville, so the travel time is about half that of Southwest, even though it costs more points. On its face, this would appear to be the winning itinerary, but it’s more difficult to acquire JetBlue’s TrueBlue points than it is to acquire Southwest Rapid Rewards points.

As a participant in Membership Rewards, Brian can transfer his points to JetBlue’s TrueBlue program at a 5:4 ratio. That means every 10,000 points he transfers count as 8,000 TrueBlue miles. Because points can be transferred in increments of 250, Brian would need 47,250 Membership Rewards points to cover all three points.

Far and away the easiest method of acquiring the necessary points is signing up for the American Express® Business Gold Rewards Card®, which pays out a 50,000 point bonus after the first $5,000 of purchases. The minimum spend requirement may be steep, but the annual fee is waived for the first year. You can learn more about this card on our Sign-Up Links page.

As discussed in our review of business credit cards, Brian may be eligible for a business credit card, even if he hasn’t considered one previously.

Where to Stay

As mentioned earlier, most hotel chains list their New York City locations several categories higher than a similar property would merit in another city due to the high demand. Most hotels charge a premium rate for cash stays, as well, meaning a fairly standard room can be several hundred dollars per night. That’s what makes stays in NYC a fantastic time to take advantage of free night certificates in lieu of points.


The Hilton HHonors® Reserve Card from Citi® awards 2 free weekend night certificates instead of points after $2,500 in purchases within 4 months (Learn more on the Sign-Up Links page). These can be used at almost any Hilton property worldwide, except those on this list.

That means these certificates can be used towards the historic New York Waldorf Astoria, at which rooms are presently listed on our favorite hotel booking site, Hotels.com, at a whopping $429 per night!

The Waldorf is just a couple blocks away from the Gershwin Theatre, where Wicked is currently playing, so it’d make for a nice stroll to the show and back!


Hyatt manages to one-up even this tremendous deal by way of their Hyatt Visa Signature® This card nets 2 free nights at any Hyatt property worldwide after $1,000 in purchases in the first 3 months. It has an annual fee of $75, but as discussed on our Sign-Up Links page, there’s a way to get a $50 statement credit that largely offsets this cost.

These free nights would be best used at the Andaz 5th Avenue. Its rates on our favorite hotel booking site, Hotels.com, are listed at an astounding $605 per night before taxes! That sums up to $1,395.48 after taxes and fees for two nights.

Our Recommendation

For the best value, we recommend that Brian sign up for the Hyatt Visa Signature® and Southwest Rapid Rewards Plus® Credit Card, using the Southwest flight itinerary recommended above and staying at the Andaz 5th Avenue by Hyatt.

The Southwest card requires $2,000 of spending and the Hyatt $1,000 of spending before paying out their promotional bonuses, but for a husband and wife working as a team and placing as many of their everyday expenses as possible on one of these two cards, this should be doable for most families within the first month.

To be most effective, we’d recommend either he and his wife both open one card each, or that he open both cards in his name only. This preserves the ability for a husband and wife to work as a team to earn twice as many bonuses.

For example, both Brian and his wife can apply individually for Southwest cards for a total of 100,000 bonus points, or they can apply together for just 50,000 points. Even if they don’t wish to apply for multiple cards a piece right now, it’s always possible to add an authorized user later on and applying individually doesn’t eliminate the possibility of doubling bonuses in the future.

Trip Component Cash Price Points + Cash Savings
Southwest: JAX to LGA Roundtrip, 2 Adults, 1 Child: 10/11/13-10/13/13 $697.80 35,457 + $30 flight fees + $69 annual fee $598.80
Andaz 5th Ave: 2 Night Stay, 2 Adults, 1 Child: 10/11/13-10/13/13 $1,395.48 $0 fees + $75 annual fee – $50 statement credit $1,370.48
Total: $2,068.28 $124 + Points $1,944.28

This doesn’t take into account that, based on the flights selected, Brian will still have at minimum 17,043 Rapid Rewards miles left over for future travel. That’s assuming he meets the 50,000 bonus with $2,000 of spending at only 1 point per $1 for all spending, and that he receives his 500 Rapid Rewards miles for signing up for a Southwest account.

At 1.67¢ per dollar on Wanna Get Away® fares, that’s an additional $284.61 of remaining value that can be applied toward a future trip! Brian would also have at least 1,000 Hyatt Gold Passport points, which I value at 2¢ a piece, or $50. So, Brian’s true savings should be at minimum $2,278.89 based on this itinerary.

Of course, availability is always limited and can change, and this trip is only a few months away, so we’d recommend Brian get started as soon as possible in order to ensure this trip can become reality.

Happy travels!

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About PointsAway
Casey Ayers is a consultant and entrepreneur with a passion for travel. After amassing enough miles and points to travel anywhere in the world for almost free in less than six months, he developed PointsAway as a way to help others make travel dreams big and small come true.
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