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How to save on a holiday trip to New York City

Summary

It’s tough to beat the Big Apple when it comes to holiday cheer. Here’s how you can book a holiday trip to New York City without cutting into your gift-buying budget.

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It’s tough to beat New York City when it comes to holiday cheer.

It seems everywhere you turn in the Big Apple there’s another Christmas tree, or another decked out store window and flashing lights (and not just the kind in Times Square) belting out Christmas merriment.

My family recently took a jaunt to the City That Never Sleeps to see the Macy’s Thanksgiving Day parade live and in person. It was quite the item to check off the bucket list, though unfortunately we had to go the year it was the coldest parade on record. Still, we enjoyed watching the balloons blown up the night before by Central Park, the Radio City Christmas Spectacular and the city’s many ice skating rinks and holiday markets.

Here are my tips for how to save if you’re considering a trip to New York City over the holidays.

See related: 5 times you should book travel through your card’s travel portal

Airfare 

My family nearly always flies Southwest Airlines because they tend to have some of the cheapest tickets paired with the best customer service, and because every year we earn the Southwest Companion Pass.

By using our Companion Pass, we are getting the best possible value. We’re flying cheaply (actually, we usually book using points) and we do not have to pay any cash or redeem any points for one ticket, which you can’t beat on pure value.

We booked this trip using Southwest points, costing us about 30,000 points total for four of us to fly, with one using the Companion Pass. We earned the points in a variety of ways – spending on our Southwest Rapid Rewards credit cards, transferring Chase Ultimate Rewards points earned using our Chase Sapphire Reserve and Chase Sapphire Preferred Card and shopping at Southwest’s Rapid Rewards Shopping portal.

A key tip with Southwest when booking with points is to repeatedly check back to see if prices have decreased. If they have decreased, you can “change” your ticket by clicking “Change/Cancel” on the Southwest home page, and it will automatically put the additional points back in your loyalty account. We were able to save about 4,500 points by rebooking our ticket twice when prices lowered.

Hotels

For our trip, we wanted to stay in Times Square. While it’s not my favorite place due to its chaos and craziness, it was a good location for all the holiday activities we wanted to do. Surprisingly, we were able to book the Crowne Plaza right in the heart of Times Square for 60,000 IHG points per night over Thanksgiving.

One of my other favorite New York hotels is EVEN Hotels Times Square South, which really is not in Times Square despite its name and is health focused from top to bottom. There is also a new Crowne Plaza HY 36 close to the new Hudson Yards development and Madison Square Garden that is uber-cool and has a fun, hip restaurant called TGA. Both are IHG properties and are bookable for 50,000 IHG points per night.

See related: 6 smart-money lessons from holiday movies

Activities

There is so much to do in New York at the holidays. A great free activity is to visit the city’s many different holiday markets like the ones at Union Square and Bryant Park. Bryant Park also has an ice skating rink that makes for a wonderful holiday outing, sipping rich hot chocolate from one of the market vendors while watching others skate – or trying it yourself.

You’ll also want to check out Saks Fifth Avenue, which has a magnificent light display set to music. (It plays every evening as soon as it starts to get dark.) Directly across is Rockefeller Center where, of course, you’ll want to see the famous gigantic Christmas tree and maybe take a stroll through FAO Schwarz. Be forewarned – you have to wait in line to shop there!

For sightseeing, I recommend getting the Gray Line Sightseeing Flex Pass, a multi-attraction pass that grants you hop-on, hop-off bus access. This can be a great way to see the city when it’s cold. You can also choose to purchase tickets to between two and 10 attractions and you’ll save up to half off versus buying each ticket directly from the attraction. Plus, the pass lets you skip the long ticket lines.

Lastly, you can’t visit New York City at Christmas without seeing the Radio City Christmas Spectacular, but these tickets are pricey. After asking several locals for tips on getting discounted tickets, we found the best savings at BroadwayBox.com, where we netted half off. We sat on the main level to the left and had a great view.

Transportation

There are lots of ways to get around New York City, from walking to cabs to Uber to the subway. The best deal depends on the weather, of course – though I like to walk whenever possible – and the number of people traveling with you.

When I visit the city with my family, cabs or Uber end up being cheapest, as we can spread the cost across four people. If I’m alone or it’s just my husband and me, I like to take the subway, where you can buy one-way tickets for as low as $2.75.

Keep in mind transportation counts as a travel expense on cards like Chase Sapphire Preferred and Chase Sapphire Reserve, so we like to use those cards to pay for transportation, enabling us to earn two and three points per dollar.

With a little strategy in hand, you can enjoy a wonderful holiday in New York City and keep more of your money for your Christmas gift list.

See related: How to use rewards points to travel to hard-to-reach destinations

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Published: December 11, 2018

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