Estimated read time: 4 minutes and 52 seconds

☀️ Good morning and welcome back to Daily Drop,

Katie here again, for one final sprint down the home stretch before Mike comes back.

My legs are cramping, and I’m tired from running… who am I kidding? I only run when I’m being chased. 😅

Hustling through an airport is my fave type of cardio, and I prefer to chase travel deals.

So, let's do my favorite kind of warm-up and run through some deals!

• 🙅‍♀️ Earn 40,000 points by saying “no”

• ✈️ United’s competitive status match

• 🏨 Earn 2x Hyatt points on Thompson stays

• 🌎 Connection that goes where you go

🙅‍♀️ Earn 40,000 points by saying “no”

If you’re comfortable making eye contact with salespeople in the mall and telling them no without a second thought, then this deal has your name all over it. 

IHG is offering a nice little vacation package starting at just $199. It includes a 4-Day, 3-Night Stay, 40,000 IHG One Rewards Points, and… a mandatory timeshare presentation.

The Holiday Inn Club Vacations arm of IHG has timeshares at nine resorts across the U.S. You can stay at them… in exchange for the opportunity to be harangued into buying a timeshare during a 2-hour presentation. Yes, it’s required in order to receive your 40,000 IHG points and keep the discounted rate.

IHG points are valued at 0.5 cpp, so 40,000 points is roughly $200, depending on how you redeem it. So not ground-breaking, though the promo hotel rate of $199 for a 3-night stay is nothing to sneeze at.

This is a good option if you’re looking for a quick, cheap getaway or already need to be in the area. Then earning 40,000 IHG points is a nice bonus, rather than something to go out of your way for. (If you’re looking for IHG points, you’d earn wayy more of them with the welcome offer on an IHG card, even the $0 annual fee one.)

So if you’re great at stonewalling salespeople, go ahead and grab this promo by September 30, 2026. But if you, like me, struggle to tell people no and hate awkward moments… maybe sit this one out. 🙈

✈️ United’s competitive status match

United Airlines is playing favorites with a recently announced special status match for Chicago residents – likely the latest maneuver in United’s fierce war with American Airlines for the city of Chicago. ⚔️

It’s one of the few major U.S. hubs where no single airline holds a monopoly, and the two carriers have been locked in a battle over gates, flight schedules, and dominance in the Windy City.

To be clear, there’s also a regular standing status match challenge you can apply for regardless of where you live – but it requires more flights to keep your status.

This one is specifically for Chicago residents. It only requires two qualifying flights (instead of the normal 5+) and the requisite Premier qualifying points to keep your matched status.

How to qualify:

• Have a Chicago metro address listed on your MileagePlus account

• Have elite status with another major airline

• Register by September 30, 2026

• Fly an “activating flight” within 90 days of registration (or in the 30 days prior)

Once registered, you’ll be matched to the corresponding MileagePlus status level for 120 days.

Keeping your matched status requires flying 2 qualifying United or United Express flights within the 120- day challenge window and earning the required Premier Qualifying Points (PQPs).

The PQP requirements are the same as the standard status match but significantly less than the amount required to earn United status from scratch.

• Premier Silver: 1,700 PQP

• Premier Gold: 3,400 PQP

• Premier Platinum: 5,000 PQP

• Premier 1K: 7,500 PQP

You can also earn PQP through credit card spending on United co-branded credit cards, which earn 1 PQP for every $20 spent (Club cards earn 1 PQP for every $15).

If you live in Chicago, this is your opportunity to pick your fighter and join a side. But if you don’t have status with another airline, you get to be a chaos agent and chase the best fare. 

May the odds be ever in your favor, Chicago. 🫡 

🏨 Earn 2x Hyatt points on Thompson stays

Thompson Hotels, one of the lifestyle brands from World of Hyatt, is celebrating 25 years by handing out bonus points on stays this fall.

It’s a pretty straightforward promo: register and stay at a Thompson Hotel by November 10, 2026 to earn 2x World of Hyatt points.

The biggest catches are the short booking window and shortlist of locations — there are only 18 Thompson Hotel properties worldwide (with two more opening soon).

The properties themselves give me moody, chic date-night vibes. The lobby could moonlight as a cocktail bar (in a good way), and they’re very much geared toward couples and upscale travelers, IMO.

I’ve personally loved my stays at the Thompson Central Park, but I’ve paid for those with points, which wouldn’t qualify for this promo.

And Megan, our Community Manager, says The Cape in Los Cabos is her favorite hotel of all time, which is high praise from a savvy traveler like her!

While I wouldn’t go out of my way for this promo, if you’re looking for a luxe getaway this fall and want to earn 2x bonus points, this could be right up your alley - just make sure to register before booking.

Alrighty y’all, I’ve had fun sharing the news over the past week (along with April and Sam), and I hope you’ve gotten something out of it too!

Be sure to give Mike a warm welcome when he’s back, all nice and refreshed, tomorrow.

See y’all around!

29.7604° N , 95.3698° W

With contributions by Sam Anthony.