Should I always take the cheapest flight?

No. The cheapest flight often costs you 5-10 extra hours of travel time. If saving $150 costs you 8 hours and your time is worth $40/hour, you're actually losing $170 of value ($320 in time minus $150 saved). The cheapest ticket is only the best deal when the time cost is acceptable.

How do I value time for a leisure trip vs a work trip?

For work trips, use your actual billing rate or 2x your salary rate—the company is paying and time directly equals money. For leisure, use 1.5x your hourly wage as a baseline, but adjust based on trip length. Short trips need higher time value because each hour is a bigger percentage of the total experience.

What if the connection saves so much money the math says take it, but it just feels wrong?

Trust your gut and add a subjective penalty to the connection. If a 14-hour routing through two cities to save $180 makes you miserable just thinking about it, add $200 to its real cost and recalculate. Sometimes the spreadsheet says one thing but your stress tolerance says another—that's valid data too.

How do I account for loyalty programs in route math?

Calculate the cash value of miles or points earned. If a route earns 8,000 miles worth 1.5 cents each, that's $120 of value. Subtract that from the ticket cost before running your hourly calculations. But don't chase miles at the expense of terrible routing—earning an extra 3,000 miles isn't worth 6 extra hours of connections.

Does this math work for trains and buses too?

Yes. Same principle: total cost divided by door-to-door time equals cost per hour. Then compare options. A $60 direct train that takes 4 hours ($15/hour) vs a $35 bus that takes 7 hours ($5/hour). You're paying $25 to save 3 hours—that's $8.33/hour. If your time is worth more than that, take the train.

How to Calculate Whether a Route Is Worth the Price

Calculate route value by dividing total cost by total travel time in hours, then comparing that hourly cost against your personal value of time and alternative routes. A route is worth it if the price difference divided by time saved is less than what you'd pay to save that time elsewhere in your life.

Calculate Your Personal Value of Time. Take your hourly wage or freelance rate and multiply by 1.5 to account for the value of vacation time. If you make $30/hour at work, your travel time is worth roughly $45/hour. If you don't have an hourly rate, use $25-50/hour as a baseline depending on your income level.
Map the Total Door-to-Door Time. Add up every minute from leaving your house to arriving at your destination accommodation. Include check-in time (2 hours for international flights, 1.5 for domestic), flight time, layovers, baggage claim (30 minutes), customs (45-60 minutes international), and ground transport on both ends. A 3-hour direct flight is really 7-8 hours door-to-door.
Calculate Cost Per Hour of Travel. Divide the total ticket price by total door-to-door hours. A $400 direct flight that takes 8 hours door-to-door costs $50/hour. A $280 one-stop flight that takes 13 hours costs $21.50/hour. The difference is $120 to save 5 hours.
Run the Value Comparison. Divide the price difference by hours saved. If saving 5 hours costs $120 extra, you're paying $24/hour to save that time. Compare that to your personal value of time. If your time is worth $45/hour and you're only paying $24/hour to save it, take the direct flight. If the math says $60/hour to save time, take the cheaper option.
Factor in Disruption Risk. Add a risk premium to connecting flights. Every connection adds a 15-25% chance of delay or missed connection. Multiply the cost of a disruption (rebooking, hotel, missed day of trip) by the probability. A connection with 20% delay risk and a $300 disruption cost adds $60 of expected cost to the route.
Adjust for Trip Context. Double your value of time for trips under 5 days—every hour matters more. Reduce it by 25% for trips over 3 weeks where schedule flexibility exists. Add $100-200 of subjective value to overnight flights that save a hotel night and arrive fresh in the morning.

Should I always take the cheapest flight?: No. The cheapest flight often costs you 5-10 extra hours of travel time. If saving $150 costs you 8 hours and your time is worth $40/hour, you're actually losing $170 of value ($320 in time minus $150 saved). The cheapest ticket is only the best deal when the time cost is acceptable.
How do I value time for a leisure trip vs a work trip?: For work trips, use your actual billing rate or 2x your salary rate—the company is paying and time directly equals money. For leisure, use 1.5x your hourly wage as a baseline, but adjust based on trip length. Short trips need higher time value because each hour is a bigger percentage of the total experience.
What if the connection saves so much money the math says take it, but it just feels wrong?: Trust your gut and add a subjective penalty to the connection. If a 14-hour routing through two cities to save $180 makes you miserable just thinking about it, add $200 to its real cost and recalculate. Sometimes the spreadsheet says one thing but your stress tolerance says another—that's valid data too.
How do I account for loyalty programs in route math?: Calculate the cash value of miles or points earned. If a route earns 8,000 miles worth 1.5 cents each, that's $120 of value. Subtract that from the ticket cost before running your hourly calculations. But don't chase miles at the expense of terrible routing—earning an extra 3,000 miles isn't worth 6 extra hours of connections.
Does this math work for trains and buses too?: Yes. Same principle: total cost divided by door-to-door time equals cost per hour. Then compare options. A $60 direct train that takes 4 hours ($15/hour) vs a $35 bus that takes 7 hours ($5/hour). You're paying $25 to save 3 hours—that's $8.33/hour. If your time is worth more than that, take the train.