Brave or Crazy? Moving from Sydney to Chicago with Our 5-Month-Old

To say it’s been a big week would be an understatement.

Two days ago – and as I write this in the early hours of the morning, jet lag still kicking in – my husband and I permanently relocated from our hometown of Sydney to the Windy City, Chicago. In the space of a week, we wrapped up our suburban life: selling cars, cancelling dog food subscriptions, giving the hedge one final trim – and then we boarded the first leg of the journey: a 14-hour flight with our five-month-old daughter.

With a travel pram and our lives packed into seven suitcases (which, I was told repeatedly, was “a lot”), we may as well have been setting sail from Old England to the colonies at the turn of the century.

We were emotionally drained from all the goodbyes with parents and grandparents, excited that the life admin of this mammoth move was finally over the second we left the tarmac, and admittedly nervous about how our daughter (or more accurately, we) would handle the long-haul flight.

Until we were seated in the airport lounge (thank you, husband’s work perks), with champagne in hand, it hadn’t sunk in. Moving to the U.S. was something I’d said so many times out loud, but with postpartum fog, sleep regressions, and all-consuming newborn life, I hadn’t truly processed what that meant.

So, on the 5th of April, in the Year of Our Lord Twenty Twenty-Five, we left the safety of the life we knew so well and stepped out in pursuit of the great American dream.

Why would we do such a thing, you ask? Why abandon stability, familiarity, and community with a baby in tow? Everyone else our age was buying cots, settling down, and picking schools?

It was a particular matrix of circumstances that led us here.

Maybe it was because, thanks to COVID, five years earlier, we hadn’t been able to travel or work overseas. Our honeymoon became a local getaway instead of the long-awaited Europe trip we’d planned for years. Maybe it was because three years ago, we were ready to move to Singapore and live the high life; until my dad was diagnosed with terminal cancer, and we stayed.

Maybe it was the three-year stretch of grief and waiting – of getting pregnant, losing the baby, trying again, and again – while our life sat in stasis. Or the difficult pregnancy that followed, where I was on bed rest, not working, not traveling, and barely coping.

So when the chance came to break the cycle and shake things up, we jumped. It was finally time to live out our dream of travel and adventure. Sure, it would look different now, with nappies instead of Negronis, but surprisingly, not that different.

On the flight, Olivia-Grace was what most people would call a dream baby. She slept through 80% of our 18 hours in the air. And I truly can’t complain. The airports were another story, where despite our best efforts with baby earmuffs, pram covers and toys, she was overwhelmed in Sydney and LA. But who could blame her? Airports are noisy, overstimulating, and generally awful.

The plane though? Pure magic. I actually think our jam-packed first five months dragging her to weddings, family events, restaurants, and everything in between, trained her for this. Once the cabin lights dimmed, she snuggled up with some rocking, shushing and mummy cuddles, and snoozed her way through the clouds.

Hot take: babies actually travel pretty well, as long as they’ve been exposed to noise and chaos from a very early age. It’s way more stressful for the parents than for the baby. From Olivia-Grace’s perspective, her “bedroom” just looked a little different. Plus, there was no “cry it out” policy mid-flight, just endless contact naps and cuddles. Bliss for a baby.

We had a bulkhead bassinet booked, but honestly, it looked more like a coffin than a crib. With the way she rolls, she’d have knocked her head repeatedly, and every patch of turbulence would’ve meant waking her up to strap her in. Instead, she slept on us, and while co-sleeping mid-air made me uneasy, we took turns staying awake to keep her safe.

Shoutout to two travel MVPs: our Milly & Coup travel pram, a New Zealand gem that folds one-handed and fits in overhead storage, and the Hackerlily Hipsurfer, which saved my arms and back when Olivia (weighing in at around 7kg) needed to be held through customs and long airport queues. She even snuck in a pram nap at LAX, which saved us from an overtired meltdown on the final 4-hour flight to Chicago. She drifted off just after takeoff, and I got to enjoy the bliss of wine and cheese with a snoozing baby in my lap. A small miracle.

Everything was going surprisingly well.

We landed in Chicago, and all our air-tagged bags made it. We had a large van waiting to take us to a serviced apartment we’d signed an 8-week lease for. Smooth sailing. We even had cash on hand to tip the driver – unlike our awkward LA moment, where we’d embarrassingly had none.

Then came the real drama.

We arrived at the apartment building at 1am, exhausted after 24 hours of travel, only to be told… they had no record of our booking. Despite showing the signed lease and all our documentation, they simply wouldn’t let us in. It was freezing outside. Olivia-Grace, who had been a dream until that point, started screaming, finally succumbing to the overstimulation of the last 24 hours.

Despite all our planning and how close we were to the end of our big journey to Chicago, we were stuck. No car seat, seven suitcases, and nowhere to go.

We made frantic calls to nearby hotels, all of whom were full. One hotel was close enough to walk to, so my husband braved the cold several times to wheel our luggage across while I sat in the lobby, near tears, with a crying baby and a group of drunk high school formal students asking to hold her (no, thank you).

Finally, the night manager, clearly moved by our desperate state, handed over a room key and told us to sort the paperwork in the morning. I could’ve cried with relief. We had a roof over our heads. A low bar, but an important one.

The next day? A reset. Olivia-Grace was her cheerful self. We ventured out into the icy Chicago streets in search of food and quickly realised: new challenge unlocked. How do you keep a baby alive and warm in the cold?

We’re still figuring that part out. But after everything we’ve survived to get here – the grief, the waiting, the packing, the flights, the freezing midnight lobby standoff – we’re feeling strangely capable.

So was it brave or crazy to move to Chicago with a five-month-old?

What do you think?

• Crazy
• Brave
• Both