Show HN: Travel Hacking Toolkit – Points search and trip planning with AI | Hacker News Reader

Show HN: Travel Hacking Toolkit – Points search and trip planning with AI

github.com

95 pointsborski41 comments

I use points and miles for most of my travel. Every booking comes down to the same decision: use points or pay cash? To answer that, you need award availability across multiple programs, cash prices, your current balances, transfer partner ratios, and the math to compare them. I got tired of doing it manually across a dozen tabs.

This toolkit teaches Claude Code and OpenCode how to do it. 7 skills (markdown files with API docs and curl examples) and 6 MCP servers (real-time tools the AI calls directly).

It searches award flights across 25+ mileage programs (Seats.aero), compares cash prices (Google Flights, Skiplagged, Kiwi.com, Duffel), pulls your loyalty balances (AwardWallet), searches hotels (Trivago, LiteAPI, Airbnb, Booking.com), finds ferry routes across 33 countries, and looks up weird hidden gems near your destination (Atlas Obscura).

Reference data is included: transfer partner ratios for Chase UR, Amex MR, Bilt, Capital One, and Citi TY. Point valuations sourced from TPG, Upgraded Points, OMAAT, and View From The Wing. Alliance membership, sweet spot redemptions, booking windows, hotel chain brand lookups.

5 of the 6 MCP servers need zero API keys. Clone, run setup.sh, start searching.

Skills are, as usual, plain markdown. They work in OpenCode and Claude Code automatically (I added a tiny setup script), and they'll work in anything else that supports skills.

PRs welcome! Help me expand the toolkit! :)

https://github.com/borski/travel-hacking-toolkit

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As someone who do the whole mileage actual thing for many years (millions of Chase and Amex points) but also a family and a full time job - IE 3 seats vs 1 and can’t leave for a trip at the drop of a hat - I’m always astonished by how worthless my miles seem to be.

I’m not convinced it’s all one big scam but a teensie bit hopeful your solution can help. Looking forward to trying. Thank you.

Oh man, do I hear that. I suspect you’ll like this; let me know what you think! Feedback greatly appreciated

Spoiler alert, it’s basically a scam

It most definitely isn't, but it takes significantly more effort than the bloggers want to make it seem like.

Yes it’s not technically a scam because it’s legal.

But it has scam smells: layering, misdirection, lock-in, very fine print, gamification, adjacent complex social media apparatuses.

I’d place it near MLMs, loot boxes, timeshares, robux, liquidity mining.

It’s not nearly as complicated as you make it out to be, and the literal point of what I posted is to try and simplify it.

An MLM or timeshare it is not.

Yes, it has gotten harder than it was a decade ago. But it is far from a “scam”

Yeah, flying my family of 5 to Hawaii using skymiles accrued on my Amex. Totally a scam.

They’re basically interchangeable with cash. I don’t get the issue. The main frustration I have is that I cant buy myself a ticket with cash and then pay skymiles for my child. If they weren’t of an age that they must be on the same reservation it wouldn’t matter. Feels more like a limitation of Delta’s abacus that sits behind their mobile app.

Agreed. Anyone interested should check out a report out of Vanderbilt, "The Loyalty Trap: How Loyalty Programs Hook Us with Deals, Hack our Brains, and Hike Our Prices."

https://consumerlaw.berkeley.edu/news/price-loyalty-how-rewa... https://cdn.vanderbilt.edu/vu-URL/wp-content/uploads/sites/4...

Small counterpoint: Working in a spot where I had visibility to various loyalty programs, several of them definitely rewarded loyalty. Big spenders would get better conversion rates than the regular consumer.

The difference here is that I’m already earning points. I’m not doing anything new to earn them; I mostly remember “restaurants on this card, online shopping on that one” and apps like CardPointers can assist if needed.

But this isn’t about selecting new loyalty programs or even being loyal; this is focused on more transferable credit card points, and airline miles you’re already earning.

It’s about using them at maximum benefit, not earning them maximally.

The big win I usually hear from family who use a lot of miles is on upgrading seats for free, which is really great because they have joint issues and fly fair number of international flights. But I think they also maintain a spreadsheet with a rotating schedule of like 10 credit card companies that are cycled (or maybe shifted between based on who has the best deal for a given good or store in any given month?) for maximum points.

What about businesses like roame.travel (YC company)? I think this toolkit just replaced services like that entirely

It uses Seats.aero under the hood, which is a Roame competitor, but I’d love to integrate it with others. Seats.aero is the only one with an API, though, which I believe is a mistake on Roame and others’ part.

The actual searching for actively available award flights is the part this relies on Seats.aero for

Having accumulated points on various platforms, in my experience, United and Alaska had much better availability for close-in flights than Delta. Dunno if there's a difference between redeeming on the Chase site versus transferring to United and then redeeming, but might be worth playing with.

Transferring is almost always the more fruitful option, but it depends on the award deals.

This looks very nice and useful!

While Trivago covers major hotel sites, I sometimes find “shady” small sites often times offer better prices for hotels. I’ve been using super.com and vio.com and they seems great.

Another complication is credit card companies’ own portal. E.g. we need to take into account Amex’s FHR or Capital One’s premier collection. They offer credits and sometimes special “stay two nights, one night free” stuff. If we are in the credit card game, then there’s also “I have X credits in the first half of the year so it’s free” situation (e.g. Hilton resort credit).

I like your inclusion of Obscura. I have a blog post of how I pick where to go to: https://blog.yanda.rocks/posts/how-i-plan-my-trips/ and my hope is one day I could automate that.

In my personal instance I actually have added the list of Chase The Edit as well as AmEx’s FHR/HC hotels. The problem is there’s no easy way to to search AmEx/Chase for those.

I’ve never booked on super.com usually because I’m not into the “any room, run of the house” that usually requires, but please lmk if I’m missing something!

And please, I am very open to PRs that improve it. :)

That’s incredible! Just having access to a list of Amex FHR/THC hotels alone is super helpful! Will check this out next trip I plan.

hey, check it out :) https://github.com/borski/travel-hacking-toolkit/pull/1

I don't know anything about capital one so can do that at a later point

Claude itself advertises this application. https://claude.com/resources/use-cases/create-a-daily-travel...

For creating an itinerary, for sure!

This is more about handling travel point hacking, credit card points and their transfer partners, comparing cash vs point prices, etc.

Plus, I like Atlas Obscura more than general internet searches for 'what to do' :)

Nice work :)

There's such a huge world of agentic automation out there outside of the hype cycle that is OpenClaw. Glad to see you putting this out there

good idea, but would've been useful 10 years ago when points and the churning game were peak.

in 2026, the optimal strategy is now:

- "want first, buy first" (pay cash when you want business class) and,

- "team cash back" for credit cards without playing the coupon book game

not worth the effort to optimize 1.5 vs 2.0 cent redemption unless it's a hobby

Nope. I just booked biz class flights to Scandinavia in August for 140k pts.

Cash was about $7k for the same flights.

In part, the reason I built this wasn't exactly to optimize 1.5cpp vs 2cpp, although that can be useful too... but rather to help me make the choice between using points vs. cash. (which, yes, is based on the cpp value).

But if you don’t find it useful, I’d love that feedback too!

> I just booked biz class flights to Scandinavia in August for 140k pts.

> Cash was about $7k for the same flights.

Cash price US$3,500

https://www.google.com/travel/flights/s/64QhvwAzsAGp8NUA7

August 5 to 12, Turkish Airlines, lie-flat business class all legs, round trip, Los Angeles to Istanbul to Oslo

points game is over, man.

but again, if it's a hobby and you like searching, winning, and finding a good deal, then sure. that has value.

Thanks for proving my point, as I was booking for 2pax, which is about $3500/pax indeed. And the 140k pts was total for both (+ ~$1200 total for fees, etc., in the interest of full disclosure).

I was booking over 3 weeks, late August to early September, and I booked on KLM/AF. I had specific date ranges I needed to hit.

Again, you don't have to like it. That's fine.

But consider that "I think points are nonsense" isn't the person this was built for. :)

> Thanks for proving my point, as I was booking for 2pax, which is about $3500/pax indeed. And the 140k pts was total for both (+ ~$1200 total for fees, etc., in the interest of full disclosure).

Again, sounds like you're trying too hard to justify 2 cpp vs 3 cpp.

Cash price $2,900/pax including fees, Aug 19 to Sep 9 (21 days), Turkish airlines lie-flat business round trip with nice short 1h30m layover at a brand new airport.

https://www.google.com/travel/flights/s/fewZVhBFrtMTn7WQ6

Versus your 70k points + $600 cash fees per person?

Especially with kids, or with high income, you stop caring about $1,000/person and care more about simplicity or having the trip vs not (e.g., departing on Friday cash vs Wednesday points)

And if one is rich with points (1 million+), then one should have no problem spending 250k points one-way business on the date of their choice. Otherwise, they can't consume their point balance.

Okay. Like I said, you don’t have to like it.

I was happy with the deal I found because my goal was saving cash, and using points I already had. I am not trying to prove a point past that.

$600/pax is a lot less than $2900/pax. Saving $4600 total to use 140k points is, indeed, very useful for me and a lot of other people.

You have other desires and needs. Cool. You could also build those into your request, but like I said: I don’t see the point you’re trying to make other than “I don’t want to like this tool because I don’t like points in general,” which is fine.

Do your thing! And I’ll do mine. :)

Related indirectly : Turkish airlines hub (Istanbul airport) is a scam. Everything there costs at least twice the price it should. Especially food which is basically what everyone does during layover. Think 30€ for a burger or a kebab.

« Brand new » is not an argument by itself. Business is a must, or at least booking a lounge.

> Everything there costs at least twice the price it should. Especially food which is basically what everyone does during layover.

Business class passengers don't pay for food.

They are eating free buffet in the lounge.

lol you conveniently left out 50% of the ticket fees

$600/pax (which I disclosed) is hardly 50% of the ticket fees, which were, as I mentioned, $3500/pax or so otherwise.

your 70k points + $600/pax is equivalent to $1300

so $600 fees is 46% of the points + cash you paid

you could've cashed out 70k points as $700, therefore the 70k points becomes cash in the math

OK, so you've calculated I've saved $2200/pax. Fine.

For the record, I already took that into account. My goal with these flights was to save cash, because at the moment, cash flow is the issue I'm solving for. At other times, I have other priorities.

I can't believe I have to say this, but... YMMV, I guess.

> Nope. I just booked biz class flights to Scandinavia in August for 140k pts.

Was it 70k points for single passenger, round-trip business class?

It's usually 100k points for one-way business class.

More likely 70k is one-way. Which means 140k points round trip + $600+ fees, vs $2900 cash price, which is hardly a deal.

It was 70k/pax round trip business class.

Yes, I agree it was a great deal.

I don't know if US miles gives better deals, but in EU (Flying Blue, KLM) Amsterdam-Munich (1hr flight) business class is 52k miles. Amsterdam - Los Angeles business class goes for 550k miles. For 1 passenger.

This was 70k round trip SFO-OSL, for 1 passenger. In general, good deals on international flying is the main win with points. Domestic can be useful too, but usually less so.

Just sent this to my partner. He’s super into travel hacking and this will be a nice add to his toolkit.

Excellent stuff, excited to try it out for an upcoming trip.

Nice! Can't wait to try it out!

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