Google Flights — Best Flight Search Engine, Period
What it does best: Date flexibility grid, price tracking, multi-city routing, and the "Explore" map for destination-flexible travelers. The calendar view showing cheapest dates per month is unmatched.
What it doesn't tell you: Google Flights doesn't include Southwest Airlines. It also subtly favors Google Hotels integration when you search packages. And it doesn't factor in credit card points value — a "more expensive" flight might be cheaper if you can transfer points.
Best prompt to pair with it:
I found these 3 flight options on Google Flights: [paste details].
Which one is the best value considering: total travel time,
airline reliability for on-time performance, seat comfort
for [my height/preferences], and whether any of these routes
frequently have upgrade availability?
Pricing: Free | Booking: Redirects to airlines/OTAs
Hopper — The "When to Buy" Oracle
What it does best: Price prediction. Hopper's AI tells you with a confidence percentage whether to buy now or wait. Their "Price Freeze" feature lets you lock a fare for a fee while you decide.
What it doesn't tell you: Hopper makes money when you book through them, so their "buy now" recommendations carry inherent bias. Their inventory is also smaller than Google Flights — they can't predict prices for flights they don't sell. Price Freeze fees ($2-$60) aren't refundable even if you don't buy.
Pricing: Free (revenue from bookings) | Price Freeze: $2-$60 per freeze
ChatGPT — The Trip Architect
What it does best: Complex, multi-constraint trip planning that no booking platform can handle. "Plan a 2-week trip through Japan for a family of 4 where one kid is vegetarian, we need wheelchair-accessible hotels, budget is $6,000 excluding flights, and we want a mix of cities and countryside." No search engine handles that — ChatGPT builds the full plan.
What it doesn't tell you: Prices in ChatGPT responses are often approximations based on training data, not real-time quotes. Hotel recommendations may include properties that have closed or changed names. Always verify availability and pricing on an actual booking platform.
Pricing: Free (GPT-4o); Plus $20/mo (higher limits)
