Wish I’d taken a bus: My 24-hour US flight nightmare

February 26, 2026 — 5:00am

It takes around two-and-a-half hours to fly direct from New York City to Chicago. Unless Chicago’s got weather, in which case it takes 24 hours, three flights, one detour, a night in an Ohio motel room and a return flight to the original point of embarkation before finally touching down in the Windy City.

This nonsensical runaround precedes our far longer, but exponentially more rational, trek: a two-and-a-half-week road trip along Route 66, which originates on Chicago’s Michigan Avenue and terminates nearly 4000 kilometres away in Santa Monica, California. My husband, two teenagers, one tween and I have taken the bus from the Upper West Side of Manhattan to La Guardia Airport, where a brusque check-in attendant informs us that our flight to O’Hare International Airport has been cancelled. Why, we inquire?

“Chicago’s got weather,” she says.

“Doesn’t everywhere have weather?” I mutter, as she bats us away.

The unspecified meteorological event that has scuppered our plans is, appropriately, “high winds”, according to Google. O’Hare’s runways are open, but incoming flights have been limited. We’re booked on another flight that leaves in six hours’ time; it will stop en route in Cleveland, Ohio.

Unbeknown to us, we’re about to experience groundhog day; in hindsight, we should’ve caught the Greyhound. Still, we must be grateful for small mercies: my frequent-flyer husband manages to get the entire clan into the airline lounge. Our children are taking the delay in their stride. What’s not to love about unlimited snacks and supersized soft drinks? Well, just the weather that’s keeping us here.

“A pox on that mistral,” I say, sipping my flute of champagne.

Finally, we’re airborne; New York twinkles far below. We still have two whole days to explore Chicago before setting off along the Main Street of America.

“The onward flight has been cancelled,” says the flight attendant as we approach Cleveland Hopkins International Airport. “Please disembark and receive instructions on the ground.”

A collective groan reverberates through the cabin. It’s late, the airport is deserted, our luggage is in limbo. A shuttle ferries us to a motel, where we brush our teeth with disposable toothbrushes and fall asleep in our clothes. Five hours later we’re back at the airport, ready for our 6am flight.

“Cancelled,” reads the board.

An irate queue is forming at the departure desk. We recognise our fellow travellers, yesterday’s outfits rumpled, hair askew, tempers flaring. Among them is a professor due to deliver an important lecture this morning; he’s close to apoplectic when the announcement comes over the PA system: “We will now be flying you back to New York.”

Bugger this, we say; let’s hire a car and drive to Chicago. But the ubiquitous TV screens are reporting black ice on Ohio’s roads; more to the point, our luggage is stowed on the plane we’ve been ordered to board. We traipse like inmates back to the seats we occupied yesterday, nodding despondently at our now-familiar neighbours. Our children relax and shuffle their playlists.

The cabin is sombre on the return journey. Arriving back at square one, our bedraggled group is directed to yet another gate. We’re tentatively optimistic: boarding for Chicago will begin shortly. For the second time in 24 hours, we take off from the Big Apple. The cabin vibrates with anticipation; chatter between strangers-turned-comrades becomes animated as we sail across Illinois. The landing is momentous: hunched shoulders slump, applause ripples through the aircraft.

The April air is so cold it knocks the breath from our lungs. The wind sends our hair spiralling. Still, there’s nothing to complain about. We’ve arrived safely. And we have one whole day to explore Chicago before heading west along the Mother Road.