With Brynn kicking off her sophomore season as an athlete on the Northeastern University volleyball team, we had one eye on the calendar and the other on the team’s schedule release. When it finally dropped, one weekend stood out immediately. They’d be playing in an early September tournament in New York City, hosted by Columbia University. Three matches in two days, all set against the backdrop of one of the world’s most iconic cities. How could we resist?

We jumped at the chance to cheer her on and explore the city in between games. Our travel crew includes Annie, her mom, and me. The two of them are seasoned NYC visitors, but for me, it’s a first-time adventure. Between matches, we’re carving out time to explore the city’s iconic sights, see a play, and maybe eat a slice (or three) of classic New York pizza.

We’re flying to New York on Thursday afternoon and returning home Sunday afternoon. It’s a whirlwind blend of family, sports, and sightseeing, and here’s how we planned our NYC getaway.

Airfare

Chicago to New York

Thanks to some leftover flight credits from previous trips, the plan was to fly United on at least one leg of the journey. The best fit turned out to be the outbound flight to New York City. Annie’s mom had her own stash of travel credits, so I booked her on a separate reservation. After applying the credits for Annie and me, the additional cost was only $16. Not a bad way to kick off a weekend in the Big Apple.

Of course, that $16 price tag is a bit of a mirage. The travel credits I used were originally purchased earlier in the year, so in reality, I’d already paid $145 for those tickets. Still, there’s something satisfying about putting those credits to good use before they expired.

New York to Chicago

For the flight home for all three of us, I paid cash for tickets on American Airlines.

Booking

When I first booked the tickets in early July, the total cash price was $625. I applied all of my $160 in travel credits to knock the price down to $465. However, later in the month, I found tickets for the exact same flight for $60 cheaper. So I cancelled the original booking and now have a $60 credit to use on future flight.

Just like with the United leg, I was able to apply some leftover travel credits to offset the upfront cost when booking. Technically, that lowered the out-of-pocket expense, but that money was already spent. So it didn’t actually make the tickets cheaper in any real sense.

What did help, though, was staying disciplined about checking fares weekly. That persistence paid off when I caught a $60 drop and immediately rebooked. Not groundbreaking, but a small win that reinforces the value of keeping tabs on pricing trends.

Hotel

New York Hilton Midtown

When it came to booking a hotel, Annie had a Hilton free night award that she received when applying for the Hilton Honors Surpass® Card. Plus, we also had tons of Hilton Honors points to use for the other nights.

For this stay, we focused on Manhattan and specifically the area just south of Central Park. There were plenty of options to choose from, but the New York Hilton Midtown stood out as the most practical and rewarding pick. It’s an upscale property with a prime location that worked well for our free night and points redemption strategy. Directly across from MoMA and surrounded by subway and bus lines, it’ll make getting around effortless. Rockefeller Center and Radio City Music Hall are just two blocks away, and Central Park is an easy walk. All in all, it checked the boxes for convenience, value, and proximity to iconic spots.

We originally were going for two nights, but had to add a third night once we saw the volleyball schedule. If I paid cash for three nights, the total would’ve been $1,332. From a points perspective, Hilton was asking for 95,000 points per night.

To use a free night award certificate with Hilton, you have to call them to book it. Annie provided the agent with her award certificate number, the stay dates, and a request to use points for the other night. Then after the fact, we added another night paying cash.

In total, we booked our 3-night stay using one free night award certificate, 95,000 Hilton points and we’ll pay $444 at the hotel. That’s a total savings of $889, plus we get to stay in the perfect location in the cultural, culinary and commercial hub of Manhattan.

New York 2025 Redemption Table

	Retail Cost	Our Cost	Miles and Points Used	Points Source
2 one-way tickets from Chicago (ORD) to New York (LGA)	$80 per person ($161 total)	$16	$145 United travel credit	- Travel credit earned from rebooking prior trip for less money
3 one-way tickets from New York (LGA) to Chicago (ORD)	$189 per person ($565 total)	$405	$160 American travel credit	- Travel credit earned from rebooking prior trip for less money
3 nights at New York Hilton Midtown	$444 per night + taxes ($1,333 total)	$444	1 free night certificate and 95,000 Hilton points	- Amex Hilton Surpass card
Total	$2,059	$865	- $145 UA travel credit - $160 AA travel credit - 1 free night certificate - 95,000 Hilton points	- $1,194 in total savings - 58% off retail cost

Bottom Line

With Brynn’s tournament anchoring the weekend, this trip is more than just a quick getaway. It’s a chance to support her on the court while soaking in the energy of New York City. All in all, I saved about 58% off the retail cost of this trip by using points, miles and credit card perks.

Trip Report Index

1. Using Points and Miles to get to New York City
2. New York Hilton Midtown