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Air travel has been especially hectic in the United States over the last week. With delays and cancellations galore, travelers need to plan for delays and even cancellations. While disruptive to most travelers, these disruptions can be lucrative for those with a flexible schedule.
I came out way ahead on my flight from Chicago (ORD) to Toronto (YYZ) last Sunday when leaving Chicago after Chicago Seminars. Here's how I leveraged a $58 basic economy flight into 40,000 bonus United MileagePlus miles.
Booking Strategy
After Chicago Seminars, my wife and I planned to fly up to Toronto, rent a car, and drive down to Niagara Falls. In all of our travels, we'd never seen this natural wonder of the world. Plus, we could utilize our Hilton Honors American Express Aspire Card resort credit at the DoubleTree by Hilton Niagara Falls — a win-win.
Even better, I could use my Hilton Aspire $200 Flight Credit — allotted up to $50 per quarter — for the flight. A Sunday evening flight from Chicago to Toronto cost just $58.30 in basic economy, meaning the credit would cover almost the entire fare.
I didn't note the price of a ‘standard' economy fare, but the price difference was enough for me to stick with the basic economy option. Thanks to my United Silver status — a benefit of my Marriott Titanium Elite status through the United-Marriott RewardsPlus partnership — I'd still be able to check a bag for free despite booking a basic economy ticket. The flight was short enough that I didn't mind potentially getting stuck in a middle seat.
Taking Advantage of Travel Waivers to Take an Earlier Flight
By the time Chicago Seminars wrapped up Sunday afternoon, Chicago's flight departure board had more yellow and red than white. My flight — originally scheduled for 6:28pm — was now delayed until 9pm.
But I was in luck. United had issued a travel waiver due to the government shutdown delays and cancellations. I had the option to switch to another flight on the same day at no additional cost. United flight #424 — originally scheduled for 1:19 pm — still hadn't left and was scheduled to depart at 7 pm. So, I switched to that flight with just a few clicks in the United app.
United showed zero seats available on the seat map, but I was assigned an Economy Plus window seat when I checked in. That meant I'd get to fly out two hours earlier and get an extra-legroom window seat. Score!
Volunteering to Be Bumped
As boarding began around 6:30pm for this 1:19pm flight, gate agents realized there was a problem. They needed six passengers to volunteer to take a later flight. The starting compensation offer: $600.
The passengers in line around me scoffed. With this flight already delayed almost six hours, the gate agent didn't get much interest. Since I'd just moved to this flight a couple of hours before, I felt it was fair for me to step forward and volunteer to help get this flight out. Plus, having paid just $58 for my flight, I knew I was likely at risk of being pulled from the flight if the gate agent needed to resort to involuntary bumps.
When volunteering, I asked what the mileage option was. After a few keystrokes, the gate agent told me that I could either get $600 or 30,000 United MileagePlus miles.
A Backup Flight
I'd snagged an American Airlines business class award for just 16,500 AAdvantage miles on a flight that was now departing at 7:40 pm. I figured I'd collect my compensation for being bumped, hop on the American Airlines flight, and then see if I could refund my United flight. If not, the worst-case scenario is that I'd lose the $8 I paid after the $50 flight credit.
Best of all, this American Airlines flight was what my wife was booked on. Her AAdvantage elite status upgrade had already cleared, so we'd even be able to sit near each other.
But unfortunately, the United gate agent was extremely slow in processing compensation for another couple that volunteered to be bumped from this flight. By the time I stepped up to the podium, that AA flight departed in 14 minutes, and I was being paged in the terminal.
Given the choice between abandoning this compensation or cancelling my American Airlines award, I opened the American Airlines app and cancelled my intended backup.
Negotiating My Compensation
Explaining to the gate agent that I just had to cancel a backup flight, I asked if he could bump the miles compensation from 30,000 to 40,000 miles. After all, I figured it couldn't hurt to ask. To my surprise, he agreed and processed the 40,000-mile compensation. I got an email almost immediately with the notification that 40,000 miles would be deposited in my account “within five business days.”
However, I wouldn't need to wait nearly that long. I woke up the next morning and checked my United app to find that United had already deposited 40,000 bonus miles in my account!
Getting Out of Chicago
After issuing my compensation, the gate agent rebooked me on flight #265 — the flight I'd originally booked. By this point, the departure time had slipped to 9:38 pm, so I checked the United app for other options. Indeed, United #3612 — originally scheduled for 4:50 pm — still hadn't departed.
The flight was “too close to departure” to move to it in the app. However, the departure board showed it still hadn't started boarding, so I figured I'd try my luck at the gate.
After a 15-minute haul across terminals, I approached the United gate agent about getting added to the standby list, noting I knew it was a long shot that I'd be able to get on. However, my United Silver status landed me much higher on the standby list than I expected. And I was lucky enough to get on that flight!
Bottom Line
I leveraged rebooking options and standby lists to fly an earlier flight than I originally booked — with an additional 40,000 United MileagePlus miles to boot! And I almost ended up catching an earlier American Airlines flight in business class for far fewer miles than I'd have received for accepting a bump from United.
While everything worked out, I'll note that I'm fortunate this ended up working out so well. A snowstorm was blowing into Chicago, air traffic control delays were mounting, and airline crews were timing out. So, I easily could have ended up stuck in Chicago overnight.
Still, this is a great example of how flyers can use rebooking tools to get on an earlier flight and leverage schedule flexibility to get compensation. Just beware of the risks when you volunteer — especially during poor weather and delays outside the airline's control, like air traffic control delays. If I really needed to make it to Toronto that night, I'd have been thrilled to have been able to switch to the earlier flight, which ended up departing around the time of my original flight.
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