"How do you have time for this?": Tools to Travel on Points Without the Hassle
The time commitment is smaller than you think and fits into a graduate student's busy schedule. Plus a cashback (or points) deal that requires minimum effort!
Often when I start talking about points and the strategies behind them, the first question I get is, "How do you have time for this?" For graduate students who are already overwhelmed with research, coursework, and everything in between, it can seem impossible to add yet another thing to the mix.
My answer? Just like anything in grad school, there are tools that make the process faster, easier, and more efficient. In this post, I’ll share some of my favorite tools, how to use them, and how they can help put your points strategy on autopilot.
(Some of the links are affiliate links, which means I might earn a commission if you click through. I’ll note which tools are free, freemium, or paid and whether I think they’re worth it.)
Finding Flights on Points
Navigating credit card transfer partners and airline alliances can quickly become overwhelming. The complexity multiplies when considering options like transferring points to both Virgin Atlantic and Air France for the same flights, while dealing with American Express transfer partnerships. Manually searching each airline's site for optimal redemption values becomes a significant time investment.
I use PointsYeah (affiliate link, free to use) after comparing it with alternatives like Point.me, Seats.Aero, and Roame.Travel. While Seats.Aero offers free 60-day searches with a $10/month premium for year-ahead viewing, American Express cardholders get free access to a dedicated Point.Me service.
PointsYeah lets you search date ranges, select your credit cards, and choose cabin preferences to find optimal point transfers and bookings. The free version works well for standard trips, though I opted for premium features for complex itineraries like my honeymoon.
The platform's standout features include:
Flexible airport and date range searches
Credit card program integration
Transfer partner analysis, including partner-to-partner options (like booking JetBlue with Etihad points)
Custom alerts for specific routes (e.g., Northeast US to Italy via various connections)
Note that PointsYeah doesn't cover all partners and has a learning curve. For simpler searches, amex.point.me might be more suitable (and free with an Amex Card).
Using PointsYeah allows you to scope out some destinations and decide how many points you’ll need and what airline partners work best for your itinerary!
Redeeming Hotel Points at Top Properties
A common frustration in the points and miles game comes when travelers discover their large point balances don't guarantee bookings at premium properties. Even with a treasure trove of Hilton points, securing reservations at top-tier hotels can prove challenging as many restrict their number of rooms allowed to be booked with points.
This issue primarily affects elite properties with limited award room availability. The demand has led to specialized tools, including paid services that send alerts when rooms become bookable with points.
Consider the Waldorf Astoria Los Cabos Pedregal in the Hilton portfolio. Rooms typically exceed $2,000 per night but cost only 140,000 Hilton points – an exceptional value at one of the world's top-ranked resorts, known for its cliffside restaurant El Farallon (A favorite of celebs including Kim Kardashian). However, only 2% of dates offer point availability, making bookings rare.
While manually checking availability each morning is possible, this becomes impractical when planning multiple trips. MaxMyPoint offers a solution, with both free and paid versions showing year-round availability. The paid version includes calendar refresh options and text alerts for specific dates.
MaxMyPoint's blue 140k bars indicate room availability. The calendar refresh and alert features are crucial for securing in-demand properties, as availability can disappear within minutes. For example, the tool's alerts helped me book the Park Hyatt Paris for my honeymoon and notified me when I could apply a Hyatt Suite Upgrade Award.
By combining PointsYeah with MaxMyPoint, you can automate both flight and hotel point searches, streamlining the booking process once you've determined your travel dates.
Double Stack: Getting Extra Cash Back (or Points) on Regular Spending
Rakuten offers cashback rewards through its browser extension and app when shopping at participating sites. After signing up, you'll receive notifications of available cashback offers ranging from 1% to 30% during promotions. These rewards stack with your credit card's existing 2-5% rewards program. Even for those not interested in points maximization, Rakuten provides an easy way to earn cashback on purchases you're already making.
Sign up here: www.rakuten.com/r/BHENRI33?eeid=28187
If you make a purchase within 90 days with Rakuten on, you’ll get $30 cashback and I’ll get $30 as well! Converting to Amex points, this means 3000 points for both of us!
Why Rakuten is a Game-Changer for Amex Cardholders
What makes Rakuten even more powerful is its partnership with American Express. If you have an Amex card that earns Membership Rewards points (like the Green, Gold, or Platinum Card), you can choose to receive your cashback as Amex points instead of cash.
Why choose points over cash? It depends on your financial goals, but for frequent travelers, points can often be redeemed at a higher value than their cash equivalent. Since I regularly use my points for flights and high-value redemptions, I find this option way more lucrative.
Real-World Example: HelloFresh + Rakuten + Amex Gold
Let’s break it down with a real example. Right now, Rakuten is offering 30% cashback on HelloFresh, a grocery and meal kit delivery service. If you opt to receive your cashback in Amex points, that’s 30 points per dollar spent.
Now, if you pay with the Amex Gold Card, which earns 4 points per dollar on groceries, you’re stacking rewards:
30 points per dollar from Rakuten
4 points per dollar from Amex Gold
Total: 34 Amex points per dollar spent
If you value Membership Rewards points at just 1 cent per point, that’s 34% cashback. But if you redeem points at a higher value (2-5 cents per point)—which is very possible for business class flights—you could be getting 68-170% value back on your spending. If you’re using Amex points for premium travel redemptions, opting to take Rakuten cashback as points is a huge multiplier. It’s one of the easiest ways to boost your rewards without spending extra—just by clicking a button before you shop.
Amazing Rakuten Deal :
Make $125/$250 off a $500 direct deposit!
Step 1: Make an account with Rakuten here for a free $30
Step 2: Search for One and you should see this offer for $250 (or $125) when you direct deposit $500 within 45 days. For those who linked Amex-Rakuten, this is 25,000 points which I’d value at $500+. (EDIT: This has now dropped to $125, still valuable but might be worth checking a different day if it’s back to $250)
Note:
One is a financial technology company and all deposits are FDIC insured.
I’ve done this before and got 25,000 points
Most companies allow you to change your direct deposit setting easily online and I change mine often for deals like this. One might be more attractive if you shop at Walmart as they offer me a lot of cashback deals for them ranging from $15 to 3-10% cash back.
To review (all links are referral links):
We use PointsYeah to find the best Business Class points deals for flights
We use MaxMyPoint to search calendars of point availability for hotels and get text alerts
We get extra points with everyday spending with Rakuten to get us more free flights (or cash!)
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