Flight Booking
Guide

How we find cheap flights, work transfer bonuses and partner airlines, and travel smarter with kids

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Finding Cheap Flights

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Google Flights — Start Here Every Time

Hands down the easiest way to find deals. The calendar view lets you browse an entire month of fares at once — perfect for flexible dates. Set a price alert and Google emails you when the fare drops. Our first stop for every trip.

✓ Free · Best Starting Point

Always book directly with the airline. If something goes wrong — delays, cancellations, seat changes — it’s significantly easier to resolve when you’re the airline’s direct customer. Third-party bookings add a layer of friction you don’t want when you’re stranded with kids.

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Booking Flights with Points

Finding award flights for a whole family is genuinely hard. Availability is limited and most search tools don’t show it well. These are the two tools we actually use.

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Points Yeah

Searches across multiple bank and airline programs at once — economy and premium. The Daydream Explorer lets you browse award availability across full months to find the best windows. Our go-to for family award bookings.

★ Best for Families

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Seats.Aero

Great for finding award space that other tools miss. Particularly useful for business and first class redemptions. Use alongside Points Yeah to cover all your bases.

✓ Great for Premium Cabins

✈️ Real Points Redemptions We’ve Done

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Hawaii from the Midwest

26K Avios per person total — 15K outbound to Oahu via American Airlines, 11K return via Alaska Airlines. Avios works across both carriers, which makes Hawaii from the middle of the country surprisingly affordable.

26K Avios/person round-trip

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Orlando (Disney/Universal)

Transferred 15K Amex points per person to Virgin Atlantic and booked return Delta flights. One of the best transfer partner values we’ve found.

15K Amex → Virgin Atlantic

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New Delhi → Chicago, Swiss Business Class

88K Avianca LifeMiles per person. A heavy spend on points — but our first time flying business class, and the kids had an absolute blast. Lie-flat seats, multi-course meals, and pajamas they still talk about.

★ 88K LifeMiles · Business Class

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Transfer Bonuses — Game Changers

Transferable credit card points (Chase, Amex, Bilt, Capital One) move to airline partners at 1:1 most of the time — but every few weeks, one of these programs runs a transfer bonus of 20–60%+. A 30% bonus turns a 100K redemption into roughly 77K. A 60% bonus turns it into 62K. These are some of the biggest single moves you can make in the points game.

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Track Bonuses at Frequent Miler

Frequent Miler’s transfer bonus tracker is the cleanest list of every current and recent bonus across all transferable currencies. Bookmark it. Check it before you transfer anything.

★ Bookmark This

🎯 Bonuses We’ve Actually Used

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Costa Rica via Bilt → Avios (60% Bonus)

Midwest to Costa Rica for our family of 4. Flights priced at 15K Avios per person each way (120K total). With the 60% transfer bonus, we only had to move 75K Bilt points to get there. Cash price would have been $2,500+ for the family.

75K Bilt · Saved $2,500+

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Tampa via Amex → Virgin Atlantic (30% Bonus)

Delta flights priced at 11K Virgin points per person each way. With Amex’s 30% bonus, the cost-per-flight dropped to roughly 8.5K Amex points each way — a meaningful discount across four tickets.

~8.5K Amex/flight

Critical rule: Confirm award space is bookable before you transfer. Transfers are one-way. If the seats disappear after you transfer, you’re stuck with airline points you may not need.

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Alliance Strategy — Book the Same Flight for Less

Major airlines are grouped into three alliances. Within each alliance, members can book each other’s flights using their own points — and the partner’s award chart is often dramatically cheaper than booking the same seat with the operating airline’s own miles. This is one of the most underused tricks in the points game.

🛩️ Oneworld: American, British Airways, Iberia, Finnair, Cathay Pacific, Qatar, Japan Airlines, and more.

✈️ SkyTeam: Delta, Air France, KLM, Korean Air, Virgin Atlantic (partner), and more.

🛬 Star Alliance: United, Air Canada, Lufthansa, Turkish, ANA, Singapore, and more.

💡 Partner Sweet Spots We Watch

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AA Flights → Book with Finnair Points

Finnair uses a static distance-based award chart that nobody talks about. It’s often the cheapest way to book American Airlines flights — including AA, Alaska, and other Oneworld partners. Hidden gem.

Oneworld

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United Flights → Book with Turkish Miles

Turkish Miles & Smiles has one of the best award charts in Star Alliance. United domestic flights for 7.5K each way is the headline deal — hard to beat.

Star Alliance

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Delta Flights → Book with Virgin Atlantic

Delta doesn’t publish an award chart, but Virgin Atlantic does — and it’s often far cheaper for the same Delta seat. Especially good for short-haul domestic and Caribbean routes.

SkyTeam Partner

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ANA Flights → Book with Virgin Atlantic

Virgin Atlantic is a transfer partner of basically everyone, and they have a sweet spot chart for ANA business and first class to Japan. Premium cabin to Tokyo for a fraction of standard pricing.

★ Premium Cabin Deal

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Loyalty Programs

👨‍👩‍👧‍👦 Sign up every family member. Even kids. Points and miles accumulate across every member of the family — those add up faster than you’d expect, especially with flights for 4.

🔗 Amex points are the most flexible. They transfer to dozens of airlines including Delta, British Airways, Air France, Virgin Atlantic, and more. One stash, many redemption options.

📺 Watch Max Miles Points on YouTube. Our go-to resource for learning the transfer game — practical, up to date, and specifically focused on maximizing airline redemptions.

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Nearby Airport Strategy

Families massively overpay because they only search one airport. Both for cash fares and award space, the airport 30–60 minutes away is often dramatically cheaper. A short ground transfer or inter-island hop can save hundreds — sometimes thousands — for a family of four.

🗾 Tokyo → consider Osaka (KIX). Award space and cash fares into Osaka are often far better. Add a Shinkansen leg and you’ve seen two cities.

🌉 SFO → consider San Jose (SJC) or Oakland (OAK). Same Bay Area, dramatically different fares. SJC is a 45-minute Caltrain ride to downtown SF.

🌴 Costa Rica → consider Liberia (LIR) instead of San Jose (SJO). If you’re heading to Guanacaste or the Pacific coast, Liberia is the smarter entry point and often cheaper.

🏝️ Hawaii → check Kona vs Maui vs Honolulu. Inter-island hops on Southwest or Hawaiian are cheap. Fly into whichever has the better deal, then hop.

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Budget Airlines — Proceed with Caution

We generally avoid Spirit and Frontier, especially with kids. But sometimes the price gap is hard to ignore — and occasionally it works out fine. Here’s our real experience to help you decide.

“We flew Spirit to Puerto Rico. Our flight was canceled days before departure. No email, no text — we only found out because we called the day before and the agent casually mentioned it. We scrambled and booked JetBlue last minute at $900 per person. Lesson learned.”

✅ When budget airlines are ok: Short domestic flights with no connection, where a cancellation isn’t catastrophic. No checked luggage, no tight schedule on arrival.

❌ When to avoid them: International trips, connecting flights, trips with non-refundable hotels or tours at the destination. The risk isn’t worth it.

💳 If you do book a budget airline: Pay with a card that has trip cancellation insurance (Chase Sapphire, Amex Platinum). At least you have a fallback if everything goes sideways.

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Family-Specific Flight Tips

Flying with kids is its own discipline. Cheapest isn’t always best — and sometimes spending a little more on the right itinerary saves you days of recovery on the back end.

“For our Japan trip return, most point deals routed through Chicago — which would have meant another flight or a 4–5 hour drive home. We paid slightly more for a direct nonstop to Detroit, an hour from our house. Worth every penny when you’re traveling with kids.”

🎯 Nonstop is worth paying for. Each connection adds risk — missed flights, lost bags, melted-down kids. With small children, a slightly pricier nonstop almost always wins.

⏰ Sweet spot layovers: 1.5–2.5 hours. Under an hour with kids and bags is too tight. Over 3 hours and they’re losing it at the gate. 90 minutes to 2.5 hours hits the goldilocks zone.

🌙 Red-eyes: depends on the kid. Older kids who can actually sleep on planes? Red-eyes are amazing — they conk out, you arrive rested. Toddlers? Usually a disaster. Know your traveler.

🥐 Airport lounges are clutch with kids. Priority Pass and Amex Centurion lounges give you food, space to spread out, and quiet zones. Worth the card annual fees if you fly more than a couple times a year.

🛏️ Bulkhead and bassinet seats. If you have a baby, request the bassinet seat early — airlines have limited supply. Bulkhead also gives older kids room to fidget without kicking the seat in front.

🧒 Car seats: bring or rent. Most US airlines let you gate-check a car seat free. Bulky to drag, but you know it’s the right one. Rental quality varies wildly — bring your own for road-trip-heavy destinations.

😴 Jet lag planning starts at home. Shift bedtimes 30 minutes per day for 3–5 days before international travel. Day one at the destination: maximize daylight outside. Saves the entire first half of the trip.

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Mistakes to Avoid

🔄 Transferring points before verifying availability. Transfers are one-way. Confirm the seats are bookable, then transfer. The number of people who’ve stranded their points in an airline program is staggering.

🎫 Booking separate tickets without buffers. Booking two one-ways on different airlines feels savvy until the first one delays and the second one is gone — no protection, no rebooking. Build in 3+ hour gaps if you go this route.

🧳 Ignoring baggage fees. A $50 fare can become a $200 fare once you add bags for a family of 4. Always price the total, not the headline.

🏦 Overpaying through bank travel portals. Portal redemptions are sometimes great (Chase Sapphire Reserve at 1.5 cpp), but transferring to an airline partner is usually better value. Always compare both before booking.

📜 Forgetting basic economy restrictions. No seat selection, no carry-on, no changes. With a family, basic economy is rarely worth it — you’ll end up sitting apart and paying upcharges anyway.

💺 Chasing business class too aggressively. Premium cabin redemptions are fun, but for a family of 4, the points math is brutal. Sometimes 4 economy seats is genuinely the right answer.

Which cards do we use? Our full credit card strategy

Our Cards →

Flight BookingGuide