Southwest flight with wheels down.

Southwest Gave Me a $300 Chicago Vacation. Here’s How It Happened

It was 5:30 pm. Sleep was a distant memory, with my bed in Kuala Lumpur, Malaysia, being the last place I had slept. That was nearly 40 hours ago. Boarding was starting at Chicago O’Hare International Airport for my second to last of five flights.

I was ready.

Unfortunately, my pilot wasn’t.

Shortly before boarding, Southwest plastered the dreaded “Delayed” word across the screen. It would only be 15 minutes, they said; the crew was on their way.

The 15-minute delay became a 25-minute delay. Anxiety grew high among passengers. Some of us had short connections.

I was still in the clear with my 80-minute layover in Baltimore, but not for long if the delays kept up.

After the third announced delay, the Southwest staff stopped anticipating when our flight would depart. They informed us that the pilot was MIA and that they had found another pilot to take his spot.

The catch?

That pilot was flying, and they couldn’t request his services until his plane landed.

No More Flights

At this point, I knew I’d miss my connection in Baltimore. I made a beeline to the Southwest counter to ask for alternative flight options. The woman’s eyes enlarged as she looked through her computer to find me a flight.

“I’m sorry, there aren’t any more flights to Baltimore tonight,” she said.

My sleep-deprived heart fluttered at the thought of a free hotel night in Chicago. But there was more.

“There aren’t flights to your final destination tomorrow either.” Poor weather the days prior was the reason, creating an influx of passengers needing to depart Chicago.

My heart sank for a split second before I realized what an incredible opportunity had seemingly been handed to me: Two free nights in Chicago with a full day to explore. It wouldn’t force me to cancel major plans with family, nor did my self-employed self have to clear the situation with my boss.

Unfortunately, my vision for a free stay in Chicago was flawed.

The Financial Caveat

The Southwest staff sympathetically informed me that she could schedule me for a direct flight to my final destination in two days at no extra charge.

Getting a direct flight was great. But that didn’t make up for being stranded in Chicago for two days due to a Southwest pilot issue.

I was informed that Southwest couldn’t guarantee they’d refund me for the hotel nights I’d have to pay. I’d have to fill out an online form and cross my fingers that they accept my request.

More than forty hours had passed since I started traveling from Kuala Lumpur; my introverted self wasn’t in the mood to challenge Southwest’s ludicrous approach. So, I reflected on how grateful I was to have the means to pay for two impromptu hotel nights.

Wait…The Wait Wasn’t Over

Even though the Southwest attendant and I knew I couldn’t make it to Baltimore that evening, I decided to hold out on leaving the airport.

Why did I do that?

The staff hadn’t canceled the flight, and the pilot hadn’t arrived yet.

Knowing that I’d have to submit a refund request that wasn’t guaranteed to be granted, I speculated that changing my flight before an official announcement about my flight’s status might not have looked good on my request.

It took about two hours from when our flight was supposed to depart to when a pilot arrived. At that point, the Southwest attendant canceled my flight, and I booked a hotel in downtown Chicago.

Two Nights Without Luggage

It’s impossible to say whether leaving the airport immediately upon realizing I missed my flight would have affected my ability to apply for a refund. The Southwest attendant kept repeating that she was very sorry but couldn’t guarantee anything at that point.

But it turned out that waiting had at least one massive downside: My luggage was already on the plane, and Southwest said they didn’t have time to take it off.

And so, I harnessed a skill I learned in the Peace Corps — washing clothes by hand — and scrubbed my clothes in my hotel’s bathroom sink.

An Impromptu Vacation

My nomadic self was in travel heaven. It was my first time visiting Chicago, and my hotel was just a few steps from the Magnificent Mile.

I took a selfie at The Bean. I gorged myself on deep-dish pizza. I took an architectural river cruise. And I gawked at each of the five floors of the largest Starbucks in the world.

Adrenaline kept me exploring, and dozens of hours of disrupted sleep stopped jet lag in its tracks.

The $300 Finger Cross

Two days later, I found myself back in the Southwest waiting area at O’Hare. My flight was on time, and I logged onto Southwest’s reimbursement request page to tackle the refund beast.

If only I had checked the form beforehand.

To my shock, I could request a refund for many items, though nothing was guaranteed. Given that Southwest withheld my luggage for two days, I could have even bought a new wardrobe.

I expensed everything: My hotel nights, Uber rides to and from the airport, my deep-dish pizza, snacks from Walgreens, and Ibuprofen. The only item I didn’t expense was my river cruise, but that was free, thanks to the perks of being a travel blogger.

Drum Roll…

I received an email from Southwest 12 days after my flight debacle saying they’d refund me in full for my $300 expenses.


They apologized for the inconvenience, and about three weeks later, my check arrived in the mail.

While I’m grateful for how things turned out and for receiving a free mini vacation in Chicago, I don’t condone how Southwest handled the situation. They should have paid for my hotel upfront. And they should have informed me of the types of expenses I could get reimbursed for, especially given that they knowingly flew away with my check-through bag.

But all in all, I’d relive this scenario over again if it meant landing another multi-day, all-expenses paid trip to a city I’ve never explored.

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