Long layover? This travel hack saved me hours at the airport, got me to my destination faster, and cost $0. | #hacking | #cybersecurity | #infosec | #comptia | #pentest | #hacker

Passengers arrive at Chicago O’Hare International Airport.Thomson Reuters

  • I recently cut a long layover very short at the airport.

  • My flight from Maui landed in Chicago with over five hours before the final leg to Philadelphia.

  • I spoke to an airline agent about changing my flight. Minutes later, I was in the air.

There’s nothing worse than waiting for what feels like an eternity at the airport for a flight — especially after you’ve just spent hours sitting on a plane.

I was prepared for this on a recent trip back from Maui to Philadelphia, with one very long stop in Chicago.

But after getting little sleep on a close-to-eight-hour, overnight flight, I didn’t want to accept that I had to wait five hours in Chicago before getting on the two-hour flight home to Philly.

With a little ingenuity, however, I found a way to avoid the wait and get home before that flight even departed. The best part? It didn’t cost me a thing.

The key to my success was simply checking the departures board to see if we could make an earlier flight

My first flight left Maui’s Kahului Airport at 5:16 p.m. local time and landed at Chicago O’Hare International Airport at 6:05 a.m. in that time zone. The next wasn’t scheduled to leave until 11:11 a.m.

I knew it’d be a hellish itinerary when I booked it, and could’ve planned to go on an earlier flight from Philadelphia from Chicago but it left just over an hour to make it in time — and that’s if there weren’t any delays. (My rule of thumb is to leave at least an hour and a half between flights.)

Of course, the flight landed early in Chicago.

Just as I was gauging my husband’s temperature (lukewarm) on leaving the airport to get breakfast in Chicago, and doing the math to work out how long we’d have once we actually got into the city proper, I remembered that flight.

I was bleary-eyed and exhausted, but in that moment, I found the energy to run to the closest departures board. There it was: the 7:25 a.m. flight to Philadelphia International Airport, with an arrival time of 10:28 a.m.

If we could catch that flight, I could be napping by 11 a.m., I thought.

I asked the airline if we could switch to an earlier flight

It was Memorial Day Monday, one of the busiest travel days of the year, but I didn’t lose hope.

We made a beeline for a nearby United gate — both of our flights were with the airline — and asked if there was room on the earlier flight.

A staff member at the gate advised us to ask an airline agent in the airport or a virtual one through United’s app about making the switch.

We couldn’t see a United agent in the part of the terminal we were in, but there was a stand with a QR code you could scan to speak to an airline agent. It pulled up a page on the United app, and I started a chat with an agent.

With the clock ticking, I was skeptical that the virtual assistant could help us in time — by this point, the flight was boarding in 20 minutes — but nevertheless I asked if we could switch, and if there’d be a fee to do so.

I was surprised when the United agent said yes, we could switch. And no, there wasn’t a fee.

Within a couple of minutes, United emailed me new boarding passes and even assigned us two seats together. Success!

united airlines

We made it onto an earlier United flight (not pictured).Nicolas Economou/NurPhoto via Getty Images

It worked!

Then we remembered our bags.

I asked the assistant if our checked luggage would make it onto the flight. They said they’d do their best, and it depended on whether the bags were scanned after we’d made the change. Worst case, we could figure it out with the airline and get a 20-minute ride from our house to the airport to pick up our stuff later.

The next challenge was getting to the gate in time. We legged it through the giant (and honestly, beautiful) airport to get to another terminal, and even had to hop on a train to get there.

Looking for the gate, I realized we had to go through security again since it was a different terminal. Not ideal in a time crunch. Thankfully, we’re both TSA PreCheck members so we got through pretty quickly.

We made it to the gate just before our group was called, albeit out of breath.

Even our bags made it, though it wasn’t a guarantee

While the plane was taxiing, I remembered the AirTags in our checked bags.

I opened the Find My app and looked for my bag, and my husband did the same. Somehow, they were in the correct terminal!

A screenshot of the Find My app shows the author's luggage in Chicago O'Hare International Airport.

AirTags to the rescue.Screenshot via the Find My app

Luckily, the rest of our journey went smoothly. Our flight left 10 minutes early, and we — and our bags — were back in Philly by 10:24 a.m., and home by 11 a.m. (10 a.m. in Chicago).

With the time difference, we would’ve had another hour and 10 minutes at the airport before our original flight. And we were snoozing in the comfort of our own home when it took off.

If you want to do something similar, here’s my advice:

Next time you have a long layover, check the departures board. Track down an airline agent to ask for a switch to an earlier time if there is one.

If there are seats available, ask if there’s a fee to switch. If there is, decide if it makes sense for your budget.

Understand that even if you make it for the flight, your bags might not. Put AirTags in your checked bags if you have them to see if they make it — if they don’t, contact the airline ASAP to make a plan to get your stuff from the airport.

Stay flexible when traveling. If this trick worked for me on one of the busiest travel weekends of the year, it might just work for you.

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