Short version: I don’t find cheap flights by refreshing a search page. I run a system of flight search tools: Google Flights to search and track, Going to bring me deals I wasn’t looking for, Hopper to tell me whether to buy now or wait, Skyscanner to cross-check the whole market, Point.me to price the same trip in points, and PointsYeah to watch for award seats when there aren’t any yet. Six tools, one job each. Below is the order I use them in, how I decide between cash and points, and the exact checklist I run before I book anything.
Disclosure, up front because this post is full of my links: I’m a creator/affiliate partner for several of the tools below — Going, Skyscanner, Point.me, and Laters.com (which shows up at the booking step). Where I have a link, it’s marked, and if you use it I may earn a commission at no extra cost to you. Two specifics, because they matter: Going gave me my Elite membership as a creator — I did not pay for the top tier, though I paid for Premium out of my own pocket for years before that upgrade — and three steps of my system pay me nothing at all: Google Flights, step one, has no affiliate program in this post, and neither do Hopper or PointsYeah. They’re still in the system, because the system is what I actually use, not what pays me. Over the next few weeks I’m publishing a full, honest breakdown of each tool.
Stop refreshing flight prices. Seriously.
We have all done it. You find a fare, you don’t book it, and then you check it again at lunch. And after dinner. And once more before bed, as if the price were a toddler who might wander off.
Here’s what my life actually looks like: I’m a pharmacist. At work, my phone access is essentially a bathroom break. I do not have a “monitor airfare all day” schedule available to me — and honestly, neither do you. Meanwhile the fare is doing whatever it wants, whenever it wants: flash sales open and close, airlines quietly reprice routes, and the good stuff does not wait for your break.
So I stopped watching prices myself and hired — mostly for free — six tools to watch them for me. Each one answers a different question:
- What’s out there? Google Flights
- What’s unusually cheap from my airports right now? Going
- Is now the right time to buy this fare? Hopper
- Did anyone else price this flight lower? Skyscanner
- What would this trip cost in points instead? Point.me
- No award seats yet — who tells me when some open up? PointsYeah
Here they are, in the order I actually use them.
1. Google Flights — where every search starts
Google Flights is the front door. It’s free, it’s fast, and it searches flights the way I think: show me the route, show me the calendar, show me what shifting a day does to the price.
The feature that runs my life is Track prices. Find the flight (or just the route), flip on tracking, and Google emails you when prices change significantly — and when a fare is likely to go up, so “I’ll book it Friday” stops being an expensive sentence. You can track specific dates, or track “Any dates” if your trip is an idea instead of an itinerary, which — real talk — is most good trips at the start.
No link for this one. Google doesn’t need my help and doesn’t pay me. It earns its spot by being the baseline every other tool gets checked against.
2. Going — the deals that find me
Google Flights answers the trip I already picked. Going answers a better question: what’s a steal from my airport right now? — and these days it hunts points deals too: economy points deals on Premium, every cabin on Elite.
Going is a deal-alert membership (it used to be Scott’s Cheap Flights). Human Flight Experts vet deals that its fare-watching tools flag — flash sales, price drops, mistake fares — and email the ones worth your time for the departure airports you follow. Mine are MSP, home, and ORD in Chicago, because I can drive there if I have to and the deals out of a hub that size are often better.
It’s not a booking site: Going finds the deal, links you to a sample search, and you book with the airline. Plans: Limited is free (a selection of continental-US economy deals), Premium is $49/year (international economy, mistake fares from your airport, points deals), and Elite is $199/year (premium cabins too, in cash and points). Both paid tiers have a 14-day free trial. And the disclosure from the top of this post, repeated where it belongs: my Elite was given to me by Going as a creator. I use it, I like it, I didn’t buy it — so my full post on Going walks through which tier I’d actually spend my own money on.
One more Going feature, and it’s the newest: Price Drop (live September 23, 2026, included free with Premium and Elite). Add a flight you’ve already booked and Going keeps watching its fare until you fly — if it drops at least 10%, you get an alert with the amount and the steps to claim the savings. It is the official end of checking the price of a flight you already own, a habit I have and am not proud of.
Get flight deals from Going →
Start free, or try Premium or Elite free for 14 days.
My full breakdown: Going: The Flight Deals That Find You
[A full Going post is coming in this series.]
3. Hopper — buy now, or wait?
Found a fare. Now the only question that matters: is this price good, or is it about to get better — or worse?
That’s Hopper’s one job. Hopper is a travel app built on price prediction: it looks at historical pricing and tells you, in plain language, whether to buy now or wait, and it’s the reason its calendar is color-coded — the cheapest dates to fly are visible at a glance instead of buried in a results list. Set a Trip Watch and it monitors the fare around the clock and notifies you the instant there’s a deal worth moving on, which is the exact job I fired myself from in the intro. Hopper says its predictions run at 95% accuracy — that’s their number, not mine, but the buy/wait call plus the price history is the part of the app I lean on: a fare is only “cheap” compared to what that route normally does, and Hopper shows you what it normally does.
Found the right fare but the group chat hasn’t confirmed yet? Hopper also offers Price Freeze — it holds the price you found so you can book it at that price when you’re ready, instead of watching it climb while three people find their passports.
Try Hopper →
Best for: the buy-now-or-wait decision, flexible dates, and fares you want watched without you.
[A full Hopper post is coming in this series.]
4. Skyscanner — the cross-check
Before I trust any fare, I run it through Skyscanner — the market’s second opinion.
Skyscanner is a free metasearch engine: it compares flights across airlines and the travel agencies selling them, in one search, including sellers a single-airline search would never show you. It does not sell you the ticket. You pick a fare, Skyscanner hands you to the airline or agency selling it, and you book there — which means your booking lives with that seller, and so do any changes later. Know that going in and it’s a feature: the widest comparison you’ve got.
Two Skyscanner habits worth stealing: “Search Everywhere” when the destination is still “somewhere warm” (it ranks where you can actually go, by price), and Whole Month view when your dates can move — plus its own price alerts, because two watchers on a fare you really want is not paranoia, it’s a system.
Full honesty, because this section has my link in it: my Skyscanner creator earnings to date total a whopping four cents. I am not retiring on this tool. I’m recommending it because the cross-check has saved me more than four cents, several times over.
Compare flights on Skyscanner →
Best for: whole-market comparison, flexible destinations, and catching the seller everyone else missed.
[A full Skyscanner post is coming in this series.]
5. Point.me — what would this cost in points?
Every fare that survives steps 1–4 gets asked one more question: or should this be a points trip?
Point.me is an award-flight search tool. One search checks 150+ airlines across 30+ loyalty programs and shows you real award availability with your actual points — Amex, Bilt, Chase, and the rest — alongside the cash price, so the cash-vs-points decision stops being a vibe. The regular plans don’t book for you and you don’t transfer through it: it finds the seat, gives you step-by-step instructions, and you transfer and book with the airline. Plans: Basic is free (limited search, up to 60 days out), Standard is $129/year, Premium is $260/year — and if you hold an eligible Amex Membership Rewards card, there’s a complimentary version that searches Amex’s transfer partners. (One update most posts get wrong: Bilt’s old free Point.me access ended March 20, 2026. Bilt points still work inside a regular
Two things people miss: you can tell Point.me which points you actually have — Amex, Bilt, Chase, airline miles — and roughly how many, and it shapes the results around your wallet instead of some generic ‘best points’ ranking. And if you’d rather not run the hunt yourself, Point.me has a concierge service (from $200 a passenger) that finds the award flights and books them with your points for you. That’s the ‘just handle it’ button.
bership.)
This is not theoretical for me. I booked four international flights — MSP to Prague, home from Budapest, peak summer, Metallica weekend — for 148,000 points total through what Point.me found, in under two hours, on flights priced around $8,000 in cash. That story, with the receipts, is the full post:
Try Point.me →
My full breakdown: How I Booked 4 International Flights for 148,000 Points
[A full Point.me post is coming in this series.]
6. PointsYeah — when the award seats aren’t there yet
Sometimes Point.me’s answer is “not yet.” Award availability is not a faucet; seats open up in dribs and drabs, and the people who get them are the people who get told.
PointsYeah is the teller. It’s an award search tool with Points Price Alerts: tell it the route, the dates, and the most points you’re willing to spend, and it watches for new award seats and price drops in the background and emails you when there’s something to book. The free account includes 4 active Points Price Alerts, which is genuinely enough for one trip’s worth of watching; Premium is $19.99/month or $119.95/year on their website if your trip list outgrows that.
This is the step that turns “no award space” from a dead end into a waiting game you’re allowed to win.
Set a points alert on PointsYeah →
Best for: award trips where the seats haven’t opened up yet — which is most award trips, at first.
[A full PointsYeah post is coming in this series.]
The booking step — and the pay-later option
However the fare gets found, the booking itself should be boring: confirm the award seat (if it’s points) before you transfer anything — transfers can’t be unsent — or book the cash fare with the airline and confirm your frequent flyer number landed on the reservation.
One extra option at this step, for the fare that’s right today but lands before payday: Laters.com lets you book the flight at today’s price and choose how to pay at checkout, including pay-later options, with the ticket issued right away and your miles still posting. I’ve vetted it in full in its own post. Two steps, every time: click my link, then use my code.
Search flights on Laters.com →
Use code CHELSEAFLY at checkout for 5% off the base fare.
My full breakdown: Laters.com, Vetted: Fly Now, Pay Later — and Still Earn Your Miles
[A full Laters.com post is coming in this series.]
Cash vs. points: how I decide
The tools give me two prices for the same trip. Then this framework, in this order, makes the call:
- Cheap cash fare? Pay cash, keep the points. If the flight is genuinely inexpensive, burning points on it is how people end up points-rich and trip-poor. Points keep; cash deals expire.
- Expensive cash fare, reasonable points price? That’s the points trip. This is the whole reason points exist. $2,000-a-ticket Europe in peak summer at 148,000 points for four people was not a hard decision, and it’s the math Point.me puts in front of you side by side.
- Both look fine? Check what the points are worth to you elsewhere. Points are a currency with an exchange rate you set. If this booking spends the exact balance earmarked for a bigger trip, pay cash here and let the bigger trip win.
- Four tickets change everything. I almost never book for one. Multiply both prices by four before deciding — a “fine” cash fare times four is a mortgage payment, and a points price times four can drain an account you built for years. Decide on the total, not the per-person number.
- When it’s close, book the one you can change. The tiebreaker isn’t price; it’s the fare rules and the award cancellation terms. Flexibility is a feature. Price it like one.
Could I run all of that by hand, airline site by airline site, alliance chart by alliance chart? I have. It took over my life on a Maldives booking once — premium cabins, multiple programs, a dozen tabs, real savings and total burnout. The system above is what replaced that. Points didn’t get less valuable. The searching got outsourced.
Travel Advisor Confession
Time for the part most travel content skips.
Most people assume travel advisors make money every time they book a flight. We usually don’t. A standalone flight, booked on its own, typically carries little or no commission for the advisor at all — the money in this business was never really in the airfare.
Package that same flight with a hotel, a cruise, or a tour through the right supplier, though, and it’s a different story: now the trip is a package, and packages are commissionable. That’s one honest reason I often suggest booking the trip as a package instead of piecing every part together across six tabs — it can simplify the planning, it can come with better support when something changes, and yes, it’s how the advisor helping you actually gets paid, usually at no extra cost to you.
And here’s my favorite version of that math: when I travel, I’m my own client. If my flight is packaged into a commissionable booking, that commission comes back to my own business. So yes — I’m probably my favorite client. It’s not why I travel. It’s a genuinely nice bonus that helps fund the next adventure, and it’s a perk of this job nobody mentions until you’re inside it.
Why tell you this in a post full of my own affiliate links? Because the tools above are for the flights you’re booking yourself, and they work whether or not I ever hear about your trip. And when you’d rather hand the whole thing — flights, hotels, the moving parts — to a human, that’s literally my job. Both things can be true, and now you know exactly how each one pays.
Chelsea’s Flight Booking Checklist
Pin this. Screenshot it. Run it in order:
- Search Google Flights — route, dates, and the calendar view, not just your first guess at dates.
- Turn on a price alert — Track prices on the route (specific dates, or “Any dates” while the trip is still an idea).
- Check Hopper’s prediction — buy now, or wait? Let the price history argue with your impatience.
- Compare cash vs. points with Point.me — same trip, both prices, side by side.
- Set a PointsYeah alert if the award space isn’t there yet — and let it watch while you live your life.
- Compare nearby airports — for me that’s MSP vs. ORD. For you it’s whatever drive you’d actually make for a real fare difference.
- Check if packaging the trip makes more sense than booking everything separately — flights plus hotel, cruise, or tour, priced both ways.
- Book it and stop watching prices. The fare you booked at a price you chose is a good fare. The one that drops $18 next Tuesday is not your business anymore.
Get the printable version — free
The Flight Tools Workbook is this checklist, expanded: fill-in blanks for the real fares you find, a tracker for all four alerts, and the cash-vs-points worksheet I run before booking anything. Print a copy for every trip.
FAQ
What is the best tool for finding cheap flights?
There isn’t one — there’s a sequence. Google Flights is the best all-round search and price tracker, Going is best for deals you weren’t looking for, Hopper is best for the buy-now-or-wait call, Skyscanner is best for cross-checking the whole market (including travel agencies), and for points trips, Point.me finds the award seats and PointsYeah alerts you when seats open up. Each tool in this post has one job, and the system is the product.
Should I pay cash or use points for a flight?
Compare the totals, not the vibes. If the cash fare is genuinely cheap, pay cash and keep your points. If the cash fare is expensive and the points price is reasonable for the route, that’s the points trip — especially for international and peak-season travel. Multiply by everyone traveling before you decide, and always confirm the award seat exists before transferring points, because transfers generally can’t be undone.
Do flight price alerts actually work?
Yes, if you let them replace checking instead of adding to it. Google Flights will email you when a tracked fare changes significantly or looks likely to rise; Going sends vetted deal alerts for your airports; Hopper watches a specific trip and notifies you when there’s a deal; PointsYeah watches award space. The alert only saves you money if booking when it fires is the plan.
Are these tools free?
Mostly, yes, at the level most people need. Google Flights and Skyscanner are free. Going has a free Limited tier. Hopper’s app and its predictions and watches are free to use (optional paid add-ons like its flexibility plans are separate). Point.me has a free Basic plan and a complimentary Amex version. PointsYeah’s free account includes 4 Points Price Alerts. Paid tiers exist for the heavy users, and each detailed post in this series breaks down exactly where free stops.
Why does a travel advisor recommend tools for booking my own flights?
Because most of my clients book some of their own flights, and I’d rather you book them well. Flights alone typically pay an advisor little or no commission anyway — where I come in is the trip around the flight: packages, hotels, cruises, tours, and the planning itself. And when I travel, I’m my own client, so I use this exact system on my own money first.
What order should I use these flight tools in?
Search and track on Google Flights; let Going surface deals for your airports; ask Hopper whether to buy now or wait; cross-check the fare on Skyscanner; price the trip in points on Point.me; and if the award seats aren’t there, set a PointsYeah alert. Then book — with the airline for cash or award tickets, or through a package or a pay-later option like Laters.com when the trip is bigger than the flight.
One Last Thought
Every cheap flight I’ve ever booked had one thing in common: somebody was watching when the price moved. For years that somebody was me, at midnight, in a dozen tabs, with a pharmacist’s schedule and a family’s worth of tickets to buy. It does not have to be you.
Set the alerts. Run the checklist. Let the tools do the refreshing — and spend your one phone break on literally anything else.
Travel smarter. Laugh harder. Explore deeper. Live kinder.
— Chelsea