2 Days in Boston: Using Credit Card Points & Perks
Published: December 9 Written by Julie Davis
Thanks to some savvy travel hacking, I joined my husband on his business trip to Boston—and turned it into a mini getaway. Even though this wasn’t technically a “points trip,” I love showing you how to maximize credit card perks and benefits to make travel more affordable and fun.
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Flights to Boston with Southwest Companion Pass
My husband flew Southwest for work, and since he earned the Southwest Companion Pass, I tagged along for just $11.20 in taxes and fees. His company covered his flight, and my ticket was practically free. If you’re not familiar, the Companion Pass lets you bring a travel buddy on any Southwest flight for only the cost of taxes—a game-changer for couples and families.
👉 Want to learn more about the Southwest Rapid Rewards Credit Card -> Southwest Rapid Rewards Priority Card
Hilton Diamond Status at DoubleTree Boston
At first, we considered Hyatt (we love Hyatt points!), but then I remembered we had Hilton Diamond Status thanks to the Hilton Aspire Card. That perk gave us a $30 daily food and beverage credit, which I happily used while my husband was at meetings.
We stayed at the DoubleTree by Hilton Boston, a walkable location near:
Boston Common 🌳
The Freedom Trail 🏰
Chinatown’s amazing restaurants 🍜
👉 If you’re looking for a Boston hotel, Hilton Aspire perks like free breakfast, upgrades, and credits make the stay even sweeter. Check out the card that stays in my wallet to give me all these perks -> Hilton Aspire Card Benefits
Lounge Life: Chase Sapphire Lounge Boston Logan
On our actual anniversary, we flew home—but not before enjoying the Chase Sapphire Lounge at Boston Logan Airport. With wine, food, and a relaxing atmosphere, it was the perfect way to end our quick trip. We get complimentary use of the Lounge with my Chase Sapphire Reserve card. Learn why this card keeps a place in my wallet -> Benefits Chase Sapphire Reserve.
👉 Access these lounges with the Chase Sapphire Reserve®, which also offers Priority Pass benefits, travel protections, and points that transfer to airlines and hotels.
Anniversary Travel Hack: Mixing Business with Pleasure
This trip wasn’t planned as a big celebration, but by combining my husband’s work travel with our perks, we enjoyed:
A nearly free flight ✈️
Daily food credits 🍴
Lounge access 🍷
Walkable sightseeing 🏙️
It’s proof that even short trips can feel special when you maximize credit card benefits.
🗺️ Things to Do in Boston (Walkable Highlights)
If you only have a couple of days, here are easy attractions near Chinatown:
Boston Common – America’s oldest public park
Freedom Trail – A 2.5-mile walk through historic sites
Faneuil Hall Marketplace – Shopping and dining in a historic setting
Chinatown Eats – Dumplings, noodles, and bubble tea galore
Final Thoughts
Boston is a city full of history, charm, and walkable adventures. By leveraging credit card perks like the Southwest Companion Pass, Hilton Diamond Status, and Chase Sapphire Lounge access, we turned a simple business trip into a stylish anniversary getaway.
Love travel hacks, cruise deals, and clever ways to explore more for less? You’re in the right place. I’m Julie—founder of No Point Left Behind, where I share smart strategies for earning points, miles, and unforgettable adventures. Whether you're just starting out or already stacking rewards like a pro, I’d love to help you travel savvier.
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