Use AI to Compare Flights with Points and Miles

Start with the flights you would actually take, not just the lowest prices you can find. Record your travel dates, points balances, comparable cash fares, award prices, and award taxes and fees. If you have transferable points, note the programs they can transfer to—but don’t move anything yet. Transfers may be irreversible, and the award you want could change or disappear.

Then add the conditions that affect the trip: baggage needs, departure times, connections, cancellation rules, and how flexible your dates are. A redemption that uses fewer points may still be a poor choice if it requires an inconvenient itinerary or leaves you with costly fees. Our checklist gives you a way to work through these inputs so your comparison reflects the trip you want to take, not just an attractive number.

For comparable flights, subtract award taxes and fees from the cash fare. Divide the result by the points required, then multiply by 100 to get cents per point.

That figure helps you compare options; it does not decide for you. A nonstop flight and a connecting flight may have different value even when the math looks favorable. Consider your schedule, baggage allowance, change rules, and whether you would rather keep cash or save miles for another trip.

Once you have current figures, ask an AI tool to arrange your options, show the cents-per-point calculation for each award, and flag missing details. You might ask: “Using only the fares and award prices below, compare these flights. Show the math, separate out fees, and identify what I still need to verify.”

Do not share passwords or full loyalty account numbers. Review the output yourself, particularly when the options differ in baggage or cancellation terms. Our checklist is a planning aid, not a source of live award prices or a connection to your loyalty accounts.

Shortlist flights that fit your schedule. Record their current cash and award costs, compare substantially similar itineraries, and weigh the terms alongside the math. When you choose, book through the appropriate provider and save your confirmation details.

For an international trip, revisit entry requirements and travel conditions through official sources before departure. The U.S. State Department’s Smart Traveler Enrollment Program (STEP) is a separate government service, not our checklist.