How We Moved from Chicago to Japan with a Dog — and What Went Wrong
Relocating overseas is never simple. Add selling a house, relocating with our dog (Jager — my Chief Barketing Officer), and downsizing from a two-story house with a basement to a small apartment, and you’ve got a recipe for adventure.
In this blog, I introduce a 12-minute video from the YouTube channel My Retired Life in Japan - We Made The Move To Japan that captures what it was really like for the YouTuber, Marco, to move from Chicago to Japan with Jager.
The journey was full of surprises — from missing paperwork to a lost passport just days before departure. For anyone considering moving abroad, especially with pets, this real-life story offers both practical lessons and encouragement.
This blog covers:
1. Marco’s Remark
2. Preparing for the Move
3. A Series of Setbacks
4. Traveling with a Pet
5. Arriving and Adjusting
6. Lessons Learned
7. Video: The Full Story
8. Wrap-Up
1.Marco’s Remark
“After spending 64 years in the U.S., I decided to pack up and make the big move to Japan. This channel is all about sharing my journey as I navigate the huge shift from life in America to life in Japan.
With over 41 years of experience working in the Japanese tech industry, I thought I was prepared for the transition. But was I really? I’ll be sharing what I’ve learned, the surprises I’ve faced, and why I chose this amazing country. So buckle up — it’s going to be a fun and interesting ride!”
🎥 Prefer to watch instead of read? Here’s We Made The Move To Japan.
2. Preparing for the Move
Like many international relocations, Marco’s move started with one of the biggest challenges: selling the home.
The Chicago housing market was sluggish at the time, adding pressure to an already stressful process. Fortunately, with the help of an experienced realtor, he managed to find the right buyer and prepare for handover.
Even so, the sale came with last-minute hurdles. The new owner requested a water system inspection and other checks, which delayed finalizing the contract by several days.
This small example shows how unpredictable selling property can be when combined with the complexity of planning an international move.
At the same time, downsizing became unavoidable. Moving from a house with a yard in suburban Chicago to an apartment near Tokyo was a major lifestyle change.
Marco chose Kamakura in Kanagawa Prefecture, a historic seaside city about 30 minutes from Tokyo by train. The location offered balance: close enough to the capital for convenience, but with a calmer pace of life.
Leaving behind a home of decades also meant parting with many possessions. Downsizing is often one of the most emotional parts of moving, but Marco chose to see it as an opportunity — a chance to reset, simplify, and focus on what really mattered.
Although it isn’t part of the video, he also attended several farewell gatherings with close friends. These goodbyes were bittersweet, but in today’s world, staying connected is easier than ever through text, email or on-line call.
Just when things seemed under control, however, the real problems began.
3. A Series of Setbacks
A few days before departure, Marco received a call from Japan Airlines. One of Jager’s required documents was missing. This was alarming — Japan has some of the strictest pet import rules in the world, and without the proper paperwork, Jager would not be allowed entry.
At the same time, while vacating the house and handing it over to the new owners, Marco discovered that his passport was missing. He had carefully stored his valuables in a drawer, but the passport was nowhere to be found — and departure was only three days away.
With no choice but to delay, Marco and Jager stayed with a close friend while he arranged a replacement passport and resubmitted documents. The process stretched to nearly a month.
To make matters worse, the new departure date ended up right after Thanksgiving, one of the busiest travel times of the year. The replacement passport arrived literally the day before the rescheduled flight. It was a nerve-wracking lead-up, but at last, the journey could begin.
4. Traveling with a Pet
When moving internationally with pets, planning ahead is essential. Airlines have strict rules about temperature, breed, and crate specifications.
In Chicago, flights can even be canceled for pets, if the outside weather is too cold, which makes winter departures especially risky.
For Jager, the requirements included:
Microchipping and multiple rabies vaccinations (all documented and up to date).
A government-issued health certificate. Even veterinarians can find the process complicated, so owners should double- and triple-check that every required document is complete.
Pre-approval of documents by Japan’s Animal Quarantine Service. Fortunately, their staff were responsive and helpful over email.
A specially approved crate suitable for the long-haul flight.
The last-minute paperwork issue underscored how unforgiving the system can be. Even a single missing signature or incorrect date can block entry. Marco’s advice to anyone making the move: always build in buffer time.
During the flight itself, Jager traveled in the cargo hold, which is pressurized and temperature-controlled. It’s stressful for both pets and owners, but with proper preparation, it can be safe.
Marco’s additional advice:
Confirm airline pet policies months in advance.
Train your pet to drink from the special water nozzle provided for crates (bowls are not allowed).
Avoid peak holiday travel whenever possible.
Keep both digital and paper copies of every document.
Prepare mentally for delays — they happen more often than you think.
For step-by-step details, I’ve also written a guide: Moving to Japan with a Dog: Jager’s Journey from Chicago.
5. Arriving and Adjusting
After four weeks of delays and setbacks, Marco and Jager finally landed at Haneda Airport in late November 2021. But the challenges weren’t over yet.
Japan’s strict Covid-19 entry restrictions were still in place at the time. All arriving passengers were required to undergo PCR testing before clearing immigration. This meant hours of waiting, and Jager had to remain in holding until Marco was officially cleared.
Arriving in Japan with a pet is always an emotional milestone. After months of paperwork, planning, and uncertainty, seeing Jager safely reunited with family brought misty eyes to Marco.
Adjusting to life in Japan also came with new realities. Living in an apartment in Kamakura, navigating smaller spaces, and integrating daily routines into a different culture took time.
Yet, the rewards — from easier access to nature to the excitement of rediscovering Japanese life after retirement — outweighed the initial challenges.
6.Lessons Learned
Looking back, Marco’s move with Jager highlighted several lessons that can help others preparing for an international relocation:
Don’t underestimate paperwork. Requirements for both humans and pets are stricter than many expect, and missing documents can halt your plans instantly.
Build in buffer time. Delays and last-minute crises are almost inevitable. He started the prep 8 months prior to the original depature, which was in October 2021.
Treat selling your house and moving abroad as separate projects. Each is demanding enough on its own.
Expect the unexpected. Lost passports, airline calls, and housing delays are more common than you might think.
Use the opportunity to downsize. Moving abroad is the perfect chance to reconsider what belongings truly matter.
Have a support network. Marco’s friend who hosted him and Jager during the delay was a lifesaver.
These lessons extend beyond pet relocation. They’re universal truths for anyone uprooting their life and starting fresh in a new country.
7.Video: The Full Story
Here’s the 12-minute video of Marco and Jager’s move from Chicago to Japan. It captures all the real-life moments.
8.Wrap-Up
Moving abroad is rarely as smooth as the guidebooks suggest. Marco’s story shows both the challenges and the rewards of making such a leap — especially with a pet. In the end, the setbacks made the arrival in Japan even more meaningful.
I’ve also seen other expats who brought their pets to Japan. For example, one of my former bosses moved with her cat, Michael.
Pets like Jager or Michael are treasured companions who help them get through the upheaval of relocation. For many expats, pets are a source of comfort, stability, and even a close connection to “home” during a life-changing move.
Have you ever moved abroad with a pet, or are you planning to? Share your story in the comments below — your experiences could help others preparing for the same big step.
For more insights on life in Japan, be sure to check out other posts on NavigatorJapan.com, and stay tuned for more features from My Retired Life in Japan YouTube channel, including:
