How we used rewards to see Hamilton in NYC, learn to cook in Italy and fly home free

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Sarah Gage

Published on April 16, 2024 | 6 min read

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Courtesy of Holly Johnson

Many rewards enthusiasts focus on getting entirely free vacations with points and miles, but that has never been my style. My family has a specific bank account we use for travel, which we fund monthly with automatic bank transfers. We mostly use airline miles, hotel points and flexible travel points from our travel rewards cards to cover flights, get more value for our travel dollars or splurge for things we wouldn’t normally want to pay for.

This is exactly how we utilized points, miles and travel loyalty programs for our fall break vacation to New York City and Italy a few years back. Due to my children’s modified year-round school schedule, we were able to take our two kids — then ages 10 and 12 at the time — on a whirlwind trip for 16 days in October.

We paid for some components of our trip with money from our travel budget and travel credits leftover from the pandemic. For example, we used leftover flight credits from Delta to fly from New York City to Rome. However, we also covered quite a bit of our trip with rewards points — for a total savings of more than $6,500. Here’s how we did it.

Flights from Indianapolis to Newark, plus airport pickup (valued at $800+)

I wanted to surprise my kids with tickets to see Hamilton on Broadway, so my first goal was to get us to New York City from Indianapolis with miles. But award flights were scarce for our date, particularly because we wanted to fly at night — after our kids got out of school.

Fortunately, I was able to book four one-way flights through the Chase travel portal to Newark, N.J., with 47,306 Chase Ultimate Rewards points. While those flights would normally cost more than $709, I was able to get them on points with 50 percent more value, due to the fact I have the Chase Sapphire Reserve®.

Since we wouldn’t get into Newark until almost midnight, I used 6,052 more Chase Ultimate Rewards points to book airport pickup and a ride to our hotel. Total cost for this part of our trip (airport pickup and hotel) worked out to 53,358 Chase Ultimate Rewards points, which netted me a savings of $800.

Note that you can search for similar redemptions directly in the Chase travel portal whether you have a cash back credit card from Chase or one of the brand’s travel credit cards. Just remember that the Chase Sapphire Reserve® is the one that lets you get 1.5 cents per point in value for travel through the portal, whereas the Chase Sapphire Preferred® Card lets you book travel at 1.25 cents per point. If you have a cash back credit card from Chase, you’ll get one cent per point in value instead.

Two nights in New York City with Hyatt (valued at $1,000+)

Next, I needed a place to stay in New York City, preferably a hotel close to Times Square and Broadway. Unfortunately, we were there over the weekend and needed a room that slept four. This meant prices were sky high, so I hoped to use hotel loyalty points to cover the cost.

I was able to find an award room with two queen beds at the Hyatt Centric Times Square New York for 25,000 Chase Ultimate Rewards points per night. World of Hyatt is a Chase transfer partner, so I transferred 50,000 UR points to my Hyatt account to make the booking.

While that’s a lot of points to fork over for two nights, the rate at this hotel (and other local hotels) over our dates was well over $500 per night. This means we got more than 2 cents value for our Chase UR points, and I’m happy with that.

Also note that today’s World of Hyatt rates for this hotel are showing slightly higher at 29,000 points per night, but on dates that also show a cash rate of $503. This means that making this redemption today might get you slightly more than 1.7 cents per point in value.

Either way, this leg of our journey was far from cheap even after taking the free hotel stay into account. We splurged for Hamilton tickets, which I had bought online very early on to avoid resale markup. We had a pretty nice dinner out before the show and did some shopping at the Hershey store and Zara. Getting to see the Big Apple through my children’s eyes was well worth it!

Using rewards points in Italy (valued at $700+)

Once we were done in New York, we hopped on our Delta flight to Rome, Italy. For our airport pickup at the Leonardo da Vinci International Airport in Fiumicino (FCO), I forked over 5,363 Chase UR points for private airport pickup in a minivan. We could have taken a train or taxi, but I love the convenience of having someone waiting at the airport holding a sign with my name on it — especially when I’m landing in a foreign country and jet-lagged from an overnight flight.

I also love how easy it is to book airport pickups through the Chase Ultimate Rewards portal. You can do this by searching for travel, then for “activities.” After that, you can filter search options to find “ground transportation” or “travel and transportation services” depending on the destination.

During our time in Italy, we stayed in Airbnbs that I paid for with cash from our travel budget. Over the course of two weeks, we visited Rome, Orvieto, Assisi, Florence, Lake Garda (Sirmione), Verona, Iseo and Lake Como. The entire trip was spectacular. We ate lots of good food, saw so much stunning scenery and had plenty of quality family time.

We also had a rental car during the second half of the trip, paid for with my Chase Sapphire Reserve card in order to use its rental car insurance. This coverage is primary and free when you pay for the rental with the card, good for up to $75,000 of theft and collision damage for rental cars in the U.S. and abroad.

We also forked over 42,994 Chase Ultimate Rewards points for a pasta cooking tutorial and dinner with a Cesarine (a certified home cook) in Verona, Italy. Since this cooking class would have cost over $600 had we paid in cash, it was a splurge in points as well, but absolutely worth it! Not only did our teacher take us out to several local markets to buy fresh ingredients, but she invited us into her home where we learned to make pasta and had an excellent meal.

My kids helped her roll the dough for tagliatelle, which we devoured along with eggplant parmesan, local cheeses, radish pie and homemade tiramisu. We washed it all down with Valpolicella, a local wine from Veneto.

Finding our way home (valued at $4,000+)

We spent the rest of our trip near Lake Como, in a village called Varenna. I didn’t want to have to travel before our early flight home, so I started looking for a hotel in Milan for the night before departure.

I used another 15,187 Ultimate Rewards points for one night at the Hilton Garden Inn Milan Malpensa, located a quick ride from the airport with a free airport shuttle that runs every 30 minutes.

This hotel would have cost me anywhere from 28,000 to 60,000 points if I’d booked with rewards within my Hilton Honors account. Booking through the Chase portal was a much better deal since that’s the kind of points I had most of at the time.

To get home from Milan to Indianapolis, I transferred 120,000 Ultimate Rewards points to United MilagePlus, another Chase travel partner, to pay for four one-way flights with the airline. This was a steal for the dates we were flying since each one-way flight was going for over $1,000 in economy.

One-way economy flights from North America to Europe cost slightly more these days, typically starting at around 40,000 miles plus taxes and fees one-way. However, award availability is pretty good if you’re flexible with your destination and dates.

In addition to the 120,000 United miles I burned, I also paid $211 in airline taxes and fees.

However, I paid those airline taxes and fees with my Chase Sapphire Reserve, and I’m glad I did. While we made the first leg of our flight to Newark, N.J., on time, the second to Indianapolis was canceled. We found ourselves stranded in Newark for 24 hours. While United covered our hotel stay, I filed a claim for our meals and Uber rides to and from the airport through my Chase card, using its travel insurance.

With the trip cancellation/interruption coverage from the Chase Sapphire Reserve, travelers get reimbursed for meals and lodging when a trip is delayed by 12 hours or more or requires an overnight stay. This benefit is worth up to $500 per ticket, which is more than we need since our hotel stay was covered by the airline. But we did pay well over $150 out-of-pocket in total over a 24-hour period, and that’s exactly what this coverage is for!

The bottom line

Paying for trips entirely with rewards sounds awfully nice, but I would rather use points and miles to stretch my travel budget further. We like to travel off the beaten path and prefer to stay in condos or Airbnbs instead of hotels. Most importantly, we like to plan our trips our way, without focusing on rewards or being steered toward whatever is free.

This fall break trip was definitely expensive, but points and miles from our rewards cards helped us avoid spending $6,500 we would have otherwise. Either way, spending this precious time with my husband and kids in New York City and Italy was priceless.