Weekend Edition / Dear Ohad...
Another week, another suitcase full of your questions. Let’s dive in before TSA flags me for emotional baggage. 7 real questions, 7 ruthless answers. From flying separately without starting a divorce to stretching your 600K Amex points into business class dreams. Buckle up.
Is transferring points to hotel programs ever better than airlines, or am I throwing points away?
– Hesitant in Houston
Dear Hesitant...
Throwing points away? Hardly. Hotels are the dependable workhorse of travel hacking, especially when you crave stability over uncertainty. Here's why:
- Hyatt routinely delivers exceptional value (think luxury stays for reasonable points).
- Hilton and Marriott offer valuable redemption sweet spots, particularly with free night certificates from their co-branded credit cards.
However, if thrill and peak luxury are your jam, airlines hold unmatched potential. Airlines are ideal for those legendary redemptions like Emirates first class or ANA business class to Tokyo for a fraction of the cash price.
Bottom line: Hotels for reliability and comfort, airlines for that mind-blowing Instagram story.
Are there economy-class award flights actually worth booking?
– Thrifty in Tampa
Dear Thrifty,
Believe it or not, economy awards can still deliver knockout value—but it all depends on where you're flying.
Great examples:
- British Airways Avios: Domestic flights on American or Alaska for as little as 7,500 Avios one-way. Perfect for short hops that cost a fortune in cash.
- Southwest Rapid Rewards: A consistent redemption value around 1.5 cents per point, making last-minute economy flights a solid deal.
- JetBlue TrueBlue: Stable redemptions that become especially valuable when cash prices spike unexpectedly.
If cash prices are high and the miles required stay low, that's your green light.
Why do I always have to call airlines to book partner awards? Is there a workaround?
– Calling-phobic in Columbus
Dear Calling-Phobic...
You don't always need to pick up the phone—but sometimes it's inevitable. Here's your cheat sheet:
- United MileagePlus: Superb online booking for Star Alliance partners—no calls needed.
- Air France/KLM Flying Blue: Solid online system for SkyTeam partners.
- British Airways Executive Club: Online ease for Oneworld short-haul flights.
Airlines like Alaska, ANA, and Turkish Airlines still love their hold music a bit too much. But remember: a short call can unlock incredible deals, making the inconvenience worthwhile.
Is holding multiple hotel credit cards genius or just overkill?
– Card Collector in Charlotte
Dear Card Collector,
Multiple hotel credit cards? You're either a points genius or you've lost control—let's aim for genius:
- Annual free-night certificates from Hilton, Marriott, and Hyatt frequently outweigh annual fees.
- Automatic status perks—breakfast, upgrades, late checkout—justify holding cards from different programs.
- Access to exclusive promotions helps diversify value.
But manage carefully:
- Choose cards from brands you use regularly.
- Keep track of annual fees and be honest about usage.
If you're strategic, multiple hotel cards can upgrade you from "occasional traveler" to "points pro."
What's the best way to dodge those pesky airline award booking fees?
– Fed-up in Fargo
Dear Fed-Up...
Award booking fees are the annoying gatekeepers of travel hacking. Beat them by:
- Using airlines that don't charge close-in booking fees: United, Avianca LifeMiles, Air Canada Aeroplan, Southwest.
- Leveraging elite status to waive fees.
- Booking partner flights through low-fee programs (e.g., Avianca LifeMiles for Star Alliance, British Airways Avios for short-haul Oneworld flights).
Stick with flexible currencies (Amex, Chase, Capital One, Citi) to sidestep fees by transferring to the most forgiving programs. Your points will thank you.
What's a foolproof method for keeping my miles organized without losing my mind?
– Disorganized in Des Moines
Dear Disorganized...
Organization is the backbone of successful travel hacking, and thankfully tech is your friend:
- AwardWallet: Tracks balances, expiry dates, and elite statuses automatically.
- Google Sheets/Excel: Customizable for advanced users who love detail.
- TripIt Pro: Combines itinerary management with loyalty tracking.
Casual hackers should stick to AwardWallet; hardcore users might enjoy a detailed spreadsheet. Choose your tool, commit, and never let another mile expire unnoticed.
Should I ever buy airline miles, or is it always a trap?
– Skeptical in Scottsdale
Dear Skeptical...
Buying miles feels risky, but occasionally it's genius-level strategic:
When it makes sense:
- To quickly top off for a specific redemption.
- During large promotional bonuses (50–100%) paired with immediate, high-value redemptions.
- Premium cabin redemptions where buying points is cheaper than paying cash.
When it's a trap:
- Buying speculatively without an immediate redemption.
- Paying full price without promotions.
- Buying miles for basic economy redemptions.
Always crunch numbers carefully—mileage purchases should be precise, strategic decisions.
Don’t settle for the middle seat of your points—aim for the lie-flats, the champagne, and the VIP treatment. Your points deserve the best. Be bold, think big, and definitely don’t waste them on an iPad.
Got questions, regrets, or upgrades that need bragging about? Hit us up at newsletter@upnonstop.com for a first-class response.
