ahoyne9New York City: The Positioning Stop That Made It All Possible 🗽🇺🇸
September 12-13, 2025
Sometimes getting to the good stuff requires a bit of bouncing around first. The main goal of this trip was to fly lie flat business class to Europe and back on points, and to make that happen the first stop was New York City. Rather than risk missing a transatlantic connection, my wife and I spent the night in Manhattan to give ourselves a comfortable buffer before the big flight out of JFK the next morning. This is a lot less stressful when booking all one-way tickets.
✈️ Getting There: United to EWR
We flew into Newark on United for $233 each. I had $225 in United Travel Bank funds from the Amex loophole which covered most of the fare. When checking in for the plane plane was mostly full and they had us in the last row by the toilet. Luckily, I was able to upgrade both of us to first class for $225 each. At first glance that sounds expensive but when you break it down it made financial sense. Seat selection to move out of the middle seats and back row would have been $70 each, checked luggage was $45 each, and first class included food on the flight. The upgrade covered all of that and then some. Effectively this upgrade was $110 more than I was expected to pay.
🚗 EWR to Manhattan: The Uber Shuttle That Got Away
I had planned for us to take the Uber Shuttle from Newark into the city, which runs a fixed route into Midtown at a significantly lower price than a standard Uber. Unfortunately we missed it and the next one was an hour away. With traffic and timing I caved and booked a regular Uber directly to the hotel. It was a bit annoying because with the first class upgrade we were supposed to have priority on the checked luggage and they came out near the last, which made us miss the shuttle.
A word of warning if you are flying into EWR and heading to Midtown Manhattan: budget for it. Between the tunnel, bridge tolls which added nearly $30 alone, surge pricing, and traffic, the total came to more than expected. The last 4.5 miles into Manhattan took 40 of the 60 minutes total. New York City traffic is its own category of painful.
Pro tip: If you do want to take the Uber Shuttle from EWR, book it in advance through the Uber app before you land and confirm your departure time. Missing it is an expensive mistake. You can miss the shuttle and just take the next one if seats are available but in this case it was already an hour to the hotel and I didn’t want to sit around for another hour.
🏨 Hyatt Herald Square: Location Over Luxury
We stayed at the Hyatt Herald Square booked for 20,000 Hyatt points, which saved us roughly $550 for the night. A solid redemption for a quick overnight.
The hotel itself is fine. It is not going to blow you away but it does not need to. The location is the whole point. Penn Station and Madison Square Garden are within easy walking distance, Times Square is a short stroll, and the subway is right there.
A few things worth knowing if you stay here:
- The hotel automatically adds an 18% gratuity to all food and drink orders, so factor that into your budget
- The rooftop bar has a genuinely great view of the Empire State Building and is worth a visit in the evening
- The rooms are compact but quiet, which matters more than anything after a travel day
New York is one of the most expensive cities in the world and the hotel pricing reflects that. At 20k points for what would have been a $550 cash night it is a decent use of Hyatt points if you need a central Manhattan base.
🎯 Times Square: Checked Off the List
We walked down to Times Square that evening and I will be honest, it was smaller than I expected. After seeing the screens in Las Vegas on the sides of skyscrapers, Times Square felt a bit more contained than its reputation suggests. Still worth seeing and now firmly on the bucket list as done. There is an energy to it that is uniquely New York even if the novelty wears off quickly.
Interesting fact: Times Square gets its name from the New York Times newspaper which moved its headquarters there in 1904. The famous New Year’s Eve ball drop has been a tradition since 1907.
🗽 September 13: A Morning in Manhattan
We had a solid 8 hours to explore the city before heading to JFK for our evening flight to Warsaw. The morning started with rain, which threw a wrench in the plans, but New York managed to deliver anyway.
I headed out solo first on the subway to the Financial District. The Charging Bull on Wall Street is smaller than most people picture it but iconic nonetheless, and the surrounding area has a great energy even early in the morning. From there I walked up to Battery Park to try to spot the Statue of Liberty through the rain and fog. Visibility was rough but you could just make her out.
Interesting fact: The Charging Bull sculpture was not commissioned by anyone. Artist Arturo Di Modica installed it illegally on Broad Street in 1989 as a guerrilla art piece and the city eventually allowed it to stay permanently. It has become one of the most photographed spots in New York.
Once the rain eased I headed back to the hotel to pick up my wife and we took the subway together for $3 each way per person down to the 9/11 Memorial and One World Trade Center. The memorial is one of the most moving public spaces I have visited anywhere in the world. The two reflecting pools sit in the exact footprints of the Twin Towers and the sheer scale of them is hard to fully appreciate until you are standing there.
One World Trade Center disappeared into the clouds that day, we could not see the top of the building at all, but it was still an impressive sight from the ground. We then walked back through to Battery Park where the fog had lifted slightly and got a better view across the water to the Statue of Liberty near the Quay.
Interesting fact: One World Trade Center stands at exactly 1,776 feet tall, a deliberate reference to the year of American independence. It is the tallest building in the Western Hemisphere.
💰 Cost Breakdown
- ✈️ United flight to EWR: $233 each ($225 covered by United Travel Bank)
- ✈️ First class upgrade: $225 each (replaced $70 seat selection + $45 baggage + food)
- 🚗 Uber EWR to Manhattan + Manhattan to JFK: $184 ($15 Amex credit applied)
- 🏨 Hyatt Herald Square (1 night): 20,000 Hyatt points (~$550 value)
- 🚇 Subway: $18 total for two
- 🍽️ Dinner and breakfast: $120
Total out of pocket: ~$1,000 after credits applied
What I would have paid without points and loopholes: Approximately $1,510 accounting for seat selection, baggage fees, and hotel cash rate.
🤔 Was It Worth It?
New York as a standalone destination for one day is expensive by any measure. But the whole point of this stop was not really New York. It was the lie flat business class seats waiting on the other side of the Atlantic that justified the positioning trip. When you factor in what those seats would have cost in cash versus what we redeemed in points, the math shifts dramatically in our favor. Not the cleanest apples to apples comparison but the kind of math that makes the points and miles game worth playing.
New York is a cool city. Times Square is a little overrated but worth seeing once. The 9/11 Memorial is genuinely unmissable. And the subway at $3 each way is one of the best deals in any major city in the world. Would I come back to do a New York Trip alone, yeah probably but I certainly would make sure to come with just a back pack, focus on public transit and use points for the hotels.
Next stop: Warsaw, Poland
Have you used a positioning flight to unlock a better redemption? Drop a comment below, I would love to hear how you structured it.