How Our One Hour Chicago Layover Became A Thirty Hour Travel Nightmare

We thought a quick plane change wouldn't be so bad. Oh, how wrong we were.
We thought a quick plane change wouldn't be so bad. Oh, how wrong we were. Photo by Schaefer Edwards

On Sunday, August 15, my fiancée and I were flying home from a trip to visit some loved ones up in Minneapolis. Weeks prior, we decided to book a return path home that had one plane change, a cute little one hour layover at Chicago’s Midway Airport we figured wouldn’t make our trip too much more stressful in the end (and would be a tad cheaper than a direct flight to boot).

We almost never book flights with plane changes involved. Meghan spent most of her adolescent years in Atlanta, and had enough experience watching harried travelers running at full-speed across the massive airport for connecting flights they were surely already doomed to miss that we knew it was always a gamble to bank on a quick and easy plane transfer. But this route home was by far the most affordable and would allow us to fit in a few more hours of time with the folks we’d come to visit and hadn’t seen in ages.

We prayed nothing would go wrong; in the end, nearly everything did.

The flight from Minneapolis to Chicago was basically perfect — we even got the two seat emergency row, the perfect seating arrangement for a tall couple on a full Southwest flight, and the trip flew by as we watched the new episode of Ted Lasso on my iPad (a Christmas special, and a delightful one at that).

We landed in Chicago just after 8 p.m. and sidled over to the gate of our flight back to Houston, which was blessedly only a few hundred feet away from where we got off plane number one. That’s when things started to feel just a tad awkward.

The Southwest attendant manning the booth at our gate made an announcement that while our plane was parked and ready to go, the crew that was supposed to man it hadn’t arrived yet (we figured they were short-handed due to the pandemic). It was looking less and less likely we’d be able to board by 8:45 as planned. Sure enough, the attendant announced an hour delay to allegedly give the crew more time to show up.

After an hour passed with still no boarding call, we were informed of a second delay, pushing back the flight yet another hour. We vented our frustrations to our parents over text messages and did our best to keep our spirits up. It had been an exhausting few hours stuck in a crowded terminal, but at least we would get home to our bed and cat in Houston within just a few hours.

Wouldn’t we?
The cavalcade of bad news texts. - SCREENSHOT BY SCHAEFER EDWARDS
The cavalcade of bad news texts.
Screenshot by Schaefer Edwards

We were eventually informed the pilot and our crew had arrived, had our butts firmly planted on the plane    (in the two-seater exit row again — score!) by 10:30 p.m. and were promised an 11 p.m. takeoff. A few minutes after being seated, our pilot gave a nearly inaudible update over the “loud”-speaker to let us know some nasty thunderstorms in Houston had been gumming up the works at Hobby Airport, causing flights in the air to divert elsewhere and preventing so many planes from taking off from Houston that there was no room in the proverbial inn for any new planes to land.

He told us all we could do was sit tight and hope conditions improved, so sit tight we did. Our patience was rewarded at 11:22 with yet another delay, this time until midnight, aka 15 minutes after we were supposed to have landed in Houston in the first place.

Exhausted and uncomfortable from having been sitting masked-up on the tarmac in limbo for so long, we were elated when the flight attendants finally closed the plane door a few minutes before midnight and began their pre-takeoff safety spiels — we were finally headed home!

Or so we thought. About five minutes later, our whisper-quiet pilot once again gave us some news no one wanted to hear in a barely audible announcement: our flight had been cancelled.

A chorus of groans, and “You’ve gotta be kidding me”s erupted. A few of the three toddlers sitting a few rows ahead of us started wailing. I hoped I had misheard the pilot’s mumbled message, but sure enough, I looked to the front of the plane and the door to the walkway popped open, and in walked the staffer who scanned our tickets to get on the infuriatingly inert plane over an hour and a half ago.

At 12:08 a.m. I got another text message that unceremoniously revealed I had been rebooked for another flight leaving Midway Airport for Houston at 2:20 pm. Monday. Meghan got a similar text, except her flight was for 9:10 p.m. Monday.

We silently left the plane to take our place in the line of angry passengers queued up along the customer service kiosk in the terminal, but as we saw more and more folks ahead of us cutting bait and walking away, we figured Southwest probably wasn’t able to offer much solace at the moment, let alone the refunds and hotel vouchers we prayed might be coming our way.

click to enlarge A queue of furious travelers formed outside the gate. - PHOTO BY MEGHAN DAVENPORT
A queue of furious travelers formed outside the gate.
Photo by Meghan Davenport
At that point, Meghan was able to book us a relatively affordable hotel through the Hotel Tonight app, which had decent enough reviews and was around half an hour away from the airport, the best combo of price and relative proximity she could find.

Then an angry flier walked down the line and yelled “No refunds, no vouchers, nothing!” As he stomped away, we figured it was probably time to head out ourselves. I asked the ticket-scanning attendant as he walked by if the customer service desk would at least be able to get Meghan and me on the same flight back, and he said they might be able to but couldn’t make any promises.

At that point, deflated and exhausted, we decided our best bet would be to try calling Southwest customer service as we heard several of our fellow pissed-off passengers doing, while trying to figure out how to get a ride. As we sat down defeated next to baggage claim, my 10 minute conversation with Southwest support proved fruitless in terms of getting us both on the same flight, refund notwithstanding. She said a team of new representatives better able to escalate and solve tricky situations like ours would be ready to take our call at 9 a.m. Monday morning.

We thought surely in the Windy City, a major American metropolis if there ever was one, there’d be at least a few taxi cabs lined up outside of the terminal, but we watched as a line of travelers formed at the taxi stand, waiting and waiting with nary a yellow cab in sight.

Our next move was to try the ride share apps. To improve our chances of finding a driver when we knew loads of them had quit the business thanks to the pandemic, my fiancée got in Lyft’s request queue, and I tried my luck with Uber, which ultimately connected us with a driver 20 minutes away.

While we weren’t thrilled at the $70 price-tag (for a trip we learned the next day would have cost around 20 bucks in non-peak demand hours), we were grateful to be connected with a silver Hyundai SUV driven by Monique, whom the app informed us was a seasoned driver with over 3,000 trips on her resume.

We arrived at the Hotel Kinzie just after 2 a.m. One of my favorite duets by rappers Kid Cudi and Kanye West was playing in the lobby, a somber yet uplifting track called Reborn that’s all about pushing forward through adversity. Temporarily uplifted by the lobby soundtrack, I tried to sweet-talk the receptionist into giving us a checkout time later than noon; the best she could do was to give us an extra hour, but said the morning staff might be able to extend that a tad longer.

Our heads finally hit pillows right around 3 a.m., and we set our alarms for 8:30 to give us enough time to snag some free continental breakfast before I planned to hop on the phone with the alleged Southwest Support A-Team.

After a restless five-ish hours of sleep, we each scarfed down some uninspiring pre-packaged muffins and I inhaled a slimy, room temperature hard boiled egg, knowing I’d need at least a smidge of protein to make it through what I figured would be an interminably long customer support call. I practiced my firm but pitiful phone negotiating voice on the morning front desk staffer at the hotel, who said we could extend our checkout all the way to 3 p.m. as long as we called to reconfirm at noon.

While Meghan caught up on sleep, I sat on hold with Southwest’s customer service line for over two hours, all the while reaching out to every Southwest social media account I could find in case that would get us through to a human more quickly, and while I tried in vain to crank out a bit of overdue copy on my iPad’s flimsy foldout keyboard.
click to enlarge Three hours, one minute, mostly on hold... wish I had been sedated. - SCREENSHOT BY SCHAEFER EDWARDS
Three hours, one minute, mostly on hold... wish I had been sedated.
Screenshot by Schaefer Edwards
I finally heard a non-recorded human voice after all that waiting, a polite woman who at least seemed intent on lending us a hand. After another hour of pathetic pleading on my part (my irate-act usually isn’t too convincing) and several more holds, I was able to convince the support rep to squeeze me in on my fiancée’s 9:10 p.m. flight. After a few more minutes of begging and not-so-subtly hinting that this was the kind of ordeal that could lead a family to cut up their Rapid Rewards credit card and never fly Southwest again, the rep even came through with a couple of $100 travel vouchers. Not quite a refund, but it was better than nothing.

Once that three-plus hour call wrapped up, Meghan trekked down to a pizza shop around the block and secured us a shareable pepperoni deep-dish pizza and a couple cups of cold brew coffee while I got just a tad more sleep. We packed up, stashed our bags in the lobby and posted up at river-front restaurant, where we semi-enjoyed some subpar nachos as we attempted to decompress before heading to the airport, all while I jotted down notes and memories of the past few hours on my iPhone that I hoped would be half-decent fodder for this story.

click to enlarge The river breeze was lovely. The midwestern nachos were not. - PHOTO BY MEGHAN DAVENPORT
The river breeze was lovely. The midwestern nachos were not.
Photo by Meghan Davenport
The rest of the afternoon and evening was blessedly uneventful. We shared a train ride to the airport, ate dinner at a surprisingly competent Irish pub once we made it through security, and were parked at our gate an hour and a half before takeoff. I busted out the iPad to take some more notes about the whole ordeal.

click to enlarge At least the train to the airport was comfortable enough. - PHOTO BY SCHAEFER EDWARDS
At least the train to the airport was comfortable enough.
Photo by Schaefer Edwards
We crossed our fingers when we saw an earlier flight to Houston had been delayed, but luckily our makeup flight home was spared. We took off and landed all on schedule. While I had foolishly figured I had enough brain cells and energy left to keep writing on the late night flight, I ended up falling asleep almost as soon as we arrived at cruising altitude. We made it back home to our West Alabama apartment and were tucked into bed with our cat just before 2 a.m. Tuesday.

click to enlarge Our intrepid reporter, too exhausted to type through his flight home. - PHOTO BY MEGHAN DAVENPORT
Our intrepid reporter, too exhausted to type through his flight home.
Photo by Meghan Davenport
At some point in the afternoon, we’d each received an additional $250 “sorry for ruining your last 30 hours” flight voucher from Southwest, so between those and the two $100 coupons I convinced customer support to toss our way, we probably nearly recouped the cost of the last-minute hotel, the expensive Uber ride there and our first flight Sunday that ended up getting cancelled.

Still, it was an exhausting ordeal, made all the more uncomfortable since we were masked-up the entire time and were made constantly fearful by some of our less than COVID-conscientious fellow travelers, especially the woman at our gate Monday night who took an un-masked Facetime video call for over half an hour; I almost laughed out loud when I saw the travel-sized bottle of hand sanitizer clipped to her backpack when we were both waiting for our checked bags back in Houston — clearly concerned about the spread of germs, she was!

Flying wasn’t fun before the pandemic. But between likely COVID-induced staff shortages, the constant uncertainty of whether our fellow travelers were fully vaccinated like us, the constant fury we felt toward all the bull-headed or misinformed mask-wearers with bare-skinned noses on full display and the always unpredictable nature of delay-inducing hurricane season downpours, we’re definitely far less eager to hop on an airplane any time soon than we were before this whole ordeal.

And we're going to be a lot warier before committing to any one-hour layovers in the future. 
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Schaefer Edwards is a staff writer at the Houston Press who covers local and regional news. A lifelong Texan and adopted Houstonian, he loves NBA basketball and devouring Tex-Mex while his cat watches in envy.
Contact: Schaefer Edwards