As Brynn’s junior volleyball season at Northeastern University got underway, we found ourselves making multiple trips to Boston this fall. Annie, her mother, and I traveled east over Labor Day weekend for a three-day home tournament. I also made a return visit in late October with my parents to watch the Huskies face Stony Brook. These weren’t the kinds of trips that generate spectacular points-and-miles stories, but with a mix of points, free night certificates, and credit card benefits, I was still able to trim the overall cost.

Airfare

September 2026

Considering it was Labor Day weekend, I was pleasantly surprised to find round-trip flights between Chicago and Boston for just $326 per person. At that price, paying cash was the clear choice and allowed me to save my points and miles for a more valuable redemption later.

October 2026

The October trip was a bit pricier, with round-trip airfare coming in at $387. Even so, I opted to pay cash rather than redeem points at a less-than-ideal value. To reduce the cost, I applied $150 in American Airlines gift cards that I’d accumulated through my Hilton Honors Aspire® Card strategy.

The card offers up to $50 in airline statement credits each quarter, for a total of up to $200 annually. While these credits are intended for incidental charges such as checked bags, seat assignments, and change fees, they have historically also been triggered by the purchase of American Airlines gift cards.

As a result, I make it a habit to purchase a $50 gift card at the start of each quarter and save it for future travel. After applying three of those gift cards, the out-of-pocket cost for my October flight dropped from $387 to just $237.

Hotel

Canopy by Hilton Boston Downtown

Boston hotel rates aren’t exactly known for being budget-friendly, so I was determined to keep our lodging costs in check. Fortunately, Annie had a Hilton Free Night Reward that she earned after spending $15,000 on her Hilton Honors Surpass® Card, which covered our first night. For the second night, we redeemed Hilton Honors points, making this a very affordable stay in an otherwise expensive hotel market.

For this trip, I wanted a hotel that would allow us to enjoy Boston between Brynn’s volleyball matches, and the Canopy by Hilton Boston Downtown checked all the boxes. The hotel’s modern design, comfortable rooms, and welcoming atmosphere made it a great home base for the weekend. Even better, its location put us within easy walking distance of Faneuil Hall, Quincy Market, and the North End’s renowned Italian restaurants. With excellent service and one of the most walkable locations in the city, the Canopy made it easy to experience some of Boston’s best historic sites and dining options whenever we had a break in the tournament schedule.

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 and a request to use 90,000 points for the other night.

In total, we booked our 2-night stay using one free night award certificate and 90,000 Hilton points. That wiped out the entire cost for a total savings of $1,545.

Residence Inn Boston Back Bay-Fenway

For my October stay, I needed to use an expiring Marriott Free Night Award, so location wasn’t nearly as important as finding a hotel with award availability. I ultimately booked the Residence Inn Boston Back Bay-Fenway, a property that consistently earns praise for its spacious suite-style rooms and complimentary breakfast.

While it’s not as centrally located as some other hotels, it’s relatively close to Brynn’s campus, making it a convenient choice for this trip. Since sightseeing wasn’t on the agenda, the extra space and included amenities made it an easy decision.

The cash rate for my stay was a staggering $491 per night, making it a perfect opportunity to put a free night certificate to use. Plus my certificate was expiring soon, so this was my last opportunity to use it. As I mentioned earlier, I earned the certificate as a cardholder of the Marriott Bonvoy Business™ American Express® Card. While the card carries a $125 annual fee, I routinely receive far more value than that each year by redeeming the annual free night award for stays that would otherwise cost several hundred dollars out of pocket.

The annual free night certificate is valid for stays costing up to 35,000 Marriott Bonvoy points, but Marriott allows members to top off the certificate with additional points when needed. In this case, the room required 59,000 points total, so I redeemed the free night certificate and added 24,000 points to complete the booking.

Using a conservative valuation of 0.7 cents per Marriott point, those 24,000 points were worth about $168. When you factor in the card’s $125 annual fee, my total “cost” for the stay was roughly $293. Considering the room was selling for $491 that night, the redemption still provided excellent value over paying the cash rate.

Boston Fall 2026 Redemption Table

	Retail Cost	Our Cost	Miles and Points Used	Points Source
September: 2 round-trip tickets from Chicago (ORD) to Boston (BOS)	$326 per person ($652 total)	$652	N/A	- N/A
September: 2 nights at Canopy by Hilton Boston Downtown	$628 per night + taxes ($1,545 total)	$0	1 free night certificate and 90,000 Hilton points	- Hilton Honors Aspire Card - Hilton Honors Surpass Card
October: 1 round-trip ticket from Chicago (ORD) to Boston (BOS)	$387	$237	$150 American Airlines gift cards	- Hilton Honors Aspire Card
October: 1 night at Residence Inn Boston Back Bay-Fenway	$422 per night + taxes ($491 total)	$0	1 free night certificate and 24,000 Marriott points	- Marriott Bonvoy Business Amex credit card
Total	$3,075	$889	- $150 AA gift cards - 2 free night certificates - 90,000 Hilton points - 24,000 Marriott points	- $2,186 in total savings - 71% off retail cost

Bottom Line

While these trips to Boston were all about watching Brynn compete for Northeastern rather than chasing outsized travel redemptions, they were a great reminder that points, miles, and credit card benefits can still deliver meaningful savings on everyday travel. By paying cash for reasonably priced flights, using American Airlines gift cards earned through card perks, redeeming a Hilton Free Night Reward and Hilton Honors points, and putting a Marriott Free Night Award to work before it expired, I was able to significantly reduce the cost of two separate trips without sacrificing convenience or comfort.

The real lesson is that maximizing travel rewards isn’t always about booking first-class flights or luxury resorts. Sometimes it’s simply about using the right tool at the right time to make family trips more affordable. And when those trips involve spending a weekend in Boston cheering on Brynn and making memories with family, that’s a redemption every bit as rewarding as the most aspirational points-and-miles booking.

Trip Report Index

1. Using Points and Miles to get to Boston