If you've been thinking about the Southwest Companion Pass, you've got until 9 AM ET tomorrow to grab an 85,000-point bonus that puts you more than halfway there. Meanwhile, American Airlines just found a new way to monetize your loyalty by pitching paid first class offers while you're trying to use upgrade certificates you earned through status. And Singapore Airlines surprised us with a 30% off award sale that's actually worth your attention.

The clock is literally ticking on one of the year's best Southwest offers. The Southwest Rapid Rewards Priority Card is offering 85,000 bonus points after spending $3,000, but the application link expires at exactly 9 AM ET on Tuesday, December 16th.

Here's why this matters beyond just the points: The card comes with 15,000 Companion Pass qualifying points built in. Add your 85,000 bonus points plus the 3,000 points you'll earn from meeting the minimum spend, and you're sitting at 88,000 toward the 135,000 needed for Companion Pass. That leaves you just 32,000 points short of a benefit that could be valid through most of 2026 and all of 2027.

For anyone who flies Southwest regularly, that math is almost too good to ignore. The remaining 32,000 points could come from everyday spending, a few flights, or one of Southwest's periodic shopping portal bonuses.

American Airlines just rolled out something that feels almost insulting to elite members. According to an internal document, the airline will now surface paid first class offers while you're actively trying to confirm an upgrade certificate. Yes, you read that correctly—while you're using the upgrade instrument you earned through loyalty spending, American will simultaneously pitch you to buy that same seat.

This represents another step in the industry's relentless march toward monetizing every aspect of premium cabins. The move suggests American sees upgrade certificates not as rewards for loyalty, but as opportunities to extract additional revenue. For those tracking American Airlines changes, this fits a broader pattern of the carrier prioritizing revenue over traditional elite benefits.

Singapore Airlines launched its monthly KrisFlyer Spontaneous Escapes promotion, offering 30% discounts on award tickets in select markets. This isn't one of those "discounts" that still leave you paying premium prices—these are legitimate savings on one of the world's best airlines across economy, premium economy, and business class.

The sale includes routes to and from the United States, making it particularly relevant for North American travelers with transferable points. Singapore is a transfer partner of Chase, Amex, Citi, Capital One, and Bilt, so most people with a healthy points balance can take advantage. Given that Singapore consistently ranks among the top carriers for service quality, getting 30% off their premium cabins represents genuine value. Check Singapore Airlines routes that work for your travel plans—this monthly sale doesn't last long.

Chase just opened registration for the Chase Freedom Flex first quarter 2026 bonus categories. If you're not familiar with how this works, the Freedom Flex offers 5x points on up to $1,500 in combined purchases each quarter in rotating categories—but you must register first.

The Q1 categories should appear in your Chase account now for activation. This matters particularly if you're in the Chase ecosystem transferring points to travel partners like United, Southwest, or Hyatt. Those 5x earnings on everyday spending can add up quickly toward your next award redemption. The Freedom Flex carries no annual fee, making it one of the better supporting actors in a points-earning strategy.

Shopping portals rarely make headlines, but today's Apple promotion deserves attention. Multiple airline shopping portals are offering up to 4x bonus miles on Apple purchases—but only for December 16th. If you were already planning to buy an iPhone, iPad, Mac, or any Apple product, routing through the right portal could net you thousands of extra miles.

This is exactly the kind of opportunistic earning that separates casual points collectors from people who maximize every purchase. The bonus works on top of whatever you'd earn from your credit card, effectively stacking earnings. Given Apple's premium pricing, even a modest percentage bonus translates to significant miles. Just remember to clear cookies, start from the portal link, and complete your purchase in one session. For more ways to boost your earning, check out our coverage of shopping portals.

Hilton just debuted its first-ever Outset Collection property with the opening of Slackline Moab in Utah. The 138-room hotel sits near Arches and Canyonlands National Parks, targeting the outdoor adventure crowd with minimalist design, extra gear storage, and community spaces.

What caught our attention weren't the wooden headboards or black accents—it was the points rates. As a new brand launch, Hilton appears to have priced Outset Collection properties aggressively for award stays, making this a potentially strong redemption option for anyone with Hilton Honors points planning a Utah national parks trip. The property focuses on experience over luxury, which in Moab makes perfect sense—you're there for the landscape, not the lobby.

If the Southwest bonus interests you at all, don't wait until morning—85,000 points plus that Companion Pass head start is worth setting an alarm. American's upgrade certificate cash grab is annoying but unsurprising given industry trends. Singapore's 30% sale represents one of the better uses of transferable points this month. And Chase Freedom registration takes 30 seconds but unlocks meaningful earning potential.

The travel loyalty landscape keeps shifting toward monetization over traditional benefits, but opportunities still exist for those paying attention. That Southwest deadline tomorrow morning is real—9 AM ET comes fast.

Before we wrap up, I wanted to share some timely opportunities I've been tracking (courtesy of our friends at AwardTravelFinder). These deals won't last long, so let's dive in.

Active transfer bonuses worth considering:

Airline programs:

Hotel programs: