Family Fun in New York City Using Southwest Points

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Lyn writes about flying on Southwest for her blog and has flown her family all over the US almost entirely free on Southwest.  I’ve asked her to share how families can visit New York City on the cheap, from flights to activities to accommodations.

Lyn:  New York City is one of my favorite places.  I love the buzz and energy of the city where there is literally always something going on, and it seems everyone is going somewhere important!

I’ve been visiting the Big Apple since I was in high school as a dancer and my love of the city lives on.  🙂

Last summer, we took our boys to the city for the first time and enjoyed a completely different experience, traveling as a family.

Planning A Family Trip To New York City With Southwest Points
New York City Is a Great Destination for Families!

I’ll show you how we got Big Travel for Small Money in New York City along with some tips for families.

Planning a Family Trip to New York City With Southwest Points

New York City is actually one of the most affordable cities for flights booked using Southwest points.  And there are plenty of free and affordable things to do, though hotels can be expensive if you are paying cash.

My family has been flying almost entirely free, largely on Southwest, since fall 2015.  New York City was high on our list of places to visit, because from our home base of Indianapolis, it’s typically less than 7,500 Southwest points per person to fly round-trip, which is a real bargain!

Planning A Family Trip To New York City With Southwest Points
We Took Our Boys to New York City for the First Time Using Southwest Points and Had Lots of Fun

By using our Southwest Companion Pass, which lets 1 person in our family always fly free (you can download my free guide to find out how easy it is to earn), we were able to fly our family of 4 to New York City for ~23,000 Southwest points.

If you don’t have enough Southwest points, you can also move Chase Ultimate Rewards points to Southwest, which transfer instantly.  We love Chase Ultimate Rewards points that we earn from our Chase Sapphire Preferred Card and Chase Sapphire Reserve cards and make this transfer a lot!

Southwest has great perks for families like 2 free checked bags per person, so you can bring snacks and all the gear you need as a family.  Plus, there’s free in-flight entertainment, no change fees, and no blackout dates for booking with points.

Southwest flies into both LaGuardia (LGA) and Newark (EWR) airports.  We have always flown into LaGuardia, which is not far from Manhattan.  But it’s currently undergoing renovation.  It feels a bit crowded and old.

LaGuardia also does NOT have a dedicated TSA PreCheck line if you hold this advanced security clearance, so plan to wait in the regular security line.

Planning A Family Trip To New York City With Southwest Points
If You Fly Into LaGuardia, You’ll Need to Take a Taxi, Uber, or Shuttle Bus Into Manhattan

From LaGuardia, you will need to take a taxi (~$25 to $30 to get to Manhattan), Uber, Lyft, shuttle bus (which takes a while, because they stop at many hotels), or private service to get into the city.

We used GoGreenRide, which was comfortable, more affordable than a taxi, private (no worries about stopping at a bunch of hotels), and could be scheduled in advance for hotel and airport pick-up.

Newark is further from the city, but you can take a train directly to midtown Manhattan.  Hop on the AirTrain, which stops at all terminals 24 hours a day, to get to the NJ TRANSIT train airport station.  Then, take a train to Penn Station in the heart of the city.  From Penn Station, you can take other subways to get to different parts of Manhattan.

Getting Around the City

While New York City is very walkable, when traveling with kids, everyone is likely to wear out quickly.  Limit your walking to a particular section of the city rather than walking from one part of the city to another.

When traveling with a family, we found that taking taxis was the most affordable and convenient way to get from place to place.  You can hail a taxi from any spot in the city (though you should try and make your way to a busy street), and share the cost across however many people in your family fit in the car.

Plus, riding a taxi in New York City is an experience unlike any other! 🙂  Read my tips for How to Hail a Taxi in New York City.

Planning A Family Trip To New York City With Southwest Points
Taxis Can Be an Affordable and Convenient Way for Families to Get Around the City

We rarely paid more than $12 by taxi for any place we traveled in Manhattan, which compared to the cost of the subway for each person was more affordable.  You can also pay your taxi driver easily by credit card via a machine in the backseat and use a card like Chase Sapphire Preferred or Chase Sapphire Reserve, which earns bonus points on travel expenses.

We’re also not keen on trying to find an Uber driver in busy cities.  It can be difficult to locate the correct driver, talk with them on the phone on a busy street to direct them to where you are, etc.

Of course, it’s a fun experience to take the subway as well, and if you’re traveling by yourself or as a couple, this may be the quickest (no worries about busy New York traffic) and most affordable.

You can easily purchase subway tickets at machines in any subway station and cost $3 for a single ride.  As you can see, for a family, that adds up quickly.  Alternately, you can purchase a 7-day Unlimited Ride MetroCard for $32 per person.  Google Maps is a fantastic tool to tell you which train to take and at which stations you’ll need to get off.

Saving on Family Activities in New York City

1.   Broadway Theater for ~75% Off!

A highlight and memorable moment for our family in New York City was taking the boys to their first Broadway show, “School of Rock,” based on the movie starring Jack Black.  This is a wonderful show for kids of any age and one we were able to secure for cheap, using SPG Moments and our Starwood Preferred Guest® Credit Card from American Express credit cards.

Planning A Family Trip To New York City With Southwest Points
We Used Our Starwood Preferred Guest Credit Cards From American Express to Book Cheap Second-Row Tickets to “School of Rock”

Here are the complete details of how I booked 4 tickets “School of Rock” on Broadway for the price of 1 and sat in the 2nd row!

In summary, we used points earned for signing-up for the personal and small business Starwood Preferred Guest® Credit Cards From American Express to purchase tickets using cash and points through the Starwood Audience Rewards program.

This ended up costing us less than 1 full-price ticket.  Other family-friendly shows in the Audience Rewards program include “Aladdin,” “The Lion King,” “Cats,” and “Charlie and the Chocolate Factory.”

2.   People-Watch and Enjoy Green Space for Free!

My favorite FREE activity in New York City is to walk the High Line.  The High Line, located in the hip Chelsea neighborhood, is a former elevated railway line that has been transformed into the most amazing park!  There’s great people-watching, fantastic architecture, and even Empire State Building views along the way.

Planning A Family Trip To New York City With Southwest Points
Walking the High Line Is One of My Favorite New York City Activities – and It’s Free!

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3.   Save on Multiple Attractions When You Buy a Pass

To save on all the other millions of things there are to do in the city from Madame Tussaud’s Wax Museum and the NBC Studio Tour (book this one in advance, because it fills up!) to the Metropolitan Museum of Art, visiting the top of 30 Rockefeller Plaza and Big Bus Tours (one of our favorite ways to get a quick overview of a city), I highly recommend multi-attraction passes that can save you 50% or more versus trying to buy each attraction separately.

These passes include the Go New York Card, CityPASS New York, and the New York Pass.  All work slightly differently, but save tons of time in research and advance purchase and allow you to skip long ticket lines.  Several also include Big Bus Tours as part of the pass.

Planning A Family Trip To New York City With Southwest Points
You Can’t Beat the Views of New York City on a Spirit of New York Cruise

4.   Treat Yourself to Amazing Views With a Cruise

For a splurge, I’d highly recommend seeing New York by water on a cruise with Spirit of New York.  You cannot beat the views of the city and the Statue of Liberty!  Choose from brunch, lunch, or dinner cruises.

A cheaper option to see the city by water would be to take the FREE Staten Island Ferry from the Whitehall Ferry Terminal, also known as South Ferry, to Staten Island and back.

Where to Stay in New York City

1.   Save by Using Points for Free Hotel Nights

There are plenty of hotels in New York City to choose from, including all major hotel brands, where you can use points from hotel credit cards or programs like Chase Ultimate Rewards to reserve rooms.

Or consider using points or free nights from cards like The Hyatt Credit CardHilton Honors™ Surpass® Card from American Express, IHG® Rewards Club Select Credit Card, or Marriott Rewards® Premier Credit Card to reduce the cost of your stay.

One of my favorites in New York City for families is IHG hotelsEVEN Hotels Times Square SouthHere’s my full review of the hotel.

Times Square is not an ideal location for families (a lot of craziness goes on there that you may not want your kids to see, like people walking around naked but with painted bodies, creepy costume Elmos, etc.).

This hotel’s location is close to Madison Square Garden, which is several blocks south of Times Square and out of the chaos, but convenient to all that Times Square offers.

Planning A Family Trip To New York City With Southwest Points
EVEN Hotels Times Square South Is Wellness-Themed and a Good Home Base for Families

EVEN Hotels is a brand that focuses entirely on wellness.  So everything from the state-of-the-art workout facility, restaurant, and rooms is designed to help you stay on track with your health while traveling.  The rooms all feature workout zones with yoga mats, stability balls, resistance bands, and more, as well as stand-up desks, cork flooring, comfy bedding, and mood lighting.

It’s ideal for families, because rooms come with refrigerators, free filtered water on select floors, and a ping-pong table on the main floor that my kids loved when ready for a break from the city.  Plus, it’s super-convenient to restaurants and activities like the High Line and Times Square.

EVEN Hotels also has locations in Midtown East close to Grand Central Station, making it easy to get anywhere in the city, as well as Brooklyn.

Planning A Family Trip To New York City With Southwest Points
Take a Break From the Action and Enjoy a Game of Ping Pong at EVEN Hotels Times Square South

We also spent several nights at boutique Hotel Elysee in a quieter area of town northeast of Times Square in Midtown East.  We loved the in-room DVD player and movie library, fold-out bed for the kids, and generally quiet respite from the city.  It has an elegant Old New York feel that makes for a great change of pace.

2.   Consider Renting a Whole Apartment for Your Famiy

Families may also want to consider options like, that has more than 2 million vacation rentals worldwide.  You can book homes and apartments with handy amenities like washer / dryers, kitchens, and separate bedrooms for more comfort in the city.  I found plenty of great options under $300 for a June stay in all different areas of town.

3.  Avoid Manhattan and Spend Less!

You could also opt to stay across the river in Newark, New Jersey, for less.  Then take the trains into the city each day.

Bottom Line

There’s no shortage of fun things to do in New York City!  And it’s certainly affordable when you use Southwest points to fly, hotel points for overnights, and enjoy free activities like walking the High Line, the Staten Island Ferry, and just checking out the city.

We even spent several hours just relaxing in Washington Square Park one afternoon at the kids’ play area!

Multi-attraction passes can also help with cost and the stress of planning, as well as taking advantage of programs like SPG Moments to book once-in-a-lifetime moments in New York City.

Do you have any tips for saving money on a family trip to New York City?  Please share in the comments!

Million Mile Secrets features a team of points and miles experts who have traveled to over 80 countries and have used 60+ credit cards responsibly to accumulate loyalty points and travel the world on the cheap! The Million Mile Secrets team has been featured on The Points Guy, TIME, Yahoo Finance and many other leading points & miles media outlets.

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! :)

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