# Two countries, one relationship, no plans to choose

> A Chicago writer flies to Winnipeg every month, and after two years the split life still beats picking a side.
- Title: Two countries, one relationship, no plans to choose | Shortify
- Summary: A Chicago writer flies to Winnipeg every month, and after two years the split life still beats picking a side. Living across two countries is a set of daily…
- Keywords: long-distance, cross-border living, canada, remote work, healthcare, business, technology, Two, countries, one, relationship, plans
- Source: Business Insider — https://businessinsider.com/we-live-in-us-and-canada-benefits-pros-cons-differences-2026-9
- Author: Catherine Collins
- Published: 2026-09-13T15:49:01.281+00:00
- Read time: 1 min
- Topics: long-distance, cross-border living, canada, remote work, healthcare, business, technology
## A week a month in the air
Every month means a two-and-a-half-hour flight from Chicago to Winnipeg to see Andrew, a partner of more than two years. Kids from previous marriages keep both of them where they are.

> For a week every month, I take a two-and-a-half-hour flight from Chicago to Winnipeg, Canada.
## Friends first, business partners now
They met a decade ago at a conference for financial bloggers and were colleagues for years before dating. The online business they run together funds all the back-and-forth.
## The apps do not cross
No Venmo or Cash App in Canada, so they settle up through Wise. A movie started on Hulu has to wait until she is back in the States.
## Chick-fil-A for poutine
Andrew stocks up on Chick-fil-A in Chicago because Winnipeg has none. She orders poutine up north, since the American A&W does not serve it.

> I often feel like I get the best of both worlds.
## Hustle on one side, calm on the other
Fifteen years of self-employment pull her toward Chicago's motivated entrepreneurs. Winnipeg runs slower, and she has started calling Canada her safe haven.

> I often think of Canada as my safe haven.
## Fast bills or long waits
Canada's tax-funded system means no surprise ER charge, but longer waits for emergencies and surgery. In the US she books appointments quickly and pays for the speed.
## Key takeaway

Living across two countries is a set of daily trade-offs, not a problem waiting to be solved by moving.