Toronto, Canada to Portland, Oregon from $329

🌍 About Portland, Oregon

Portland's signature isn't a monument — it's the absence of sales tax, so the price on the shelf is the price you pay, which makes Powell's City of Books a genuine event: a full city block of new and used titles, color-coded rooms, the largest independent bookstore in the US. Eat marionberry anything (pie, jam, ice cream) — the marionberry is a blackberry bred at Oregon State in the 1940s and grown almost nowhere else. The food carts, clustered in "pods" across downtown and the east side, are the real dinner move, not the sit-down restaurants. Come July through September: it's reliably dry and warm, and Forest Park and the Columbia Gorge waterfalls are at their best. The rest of the year earns Portland its gray, drizzly reputation — mild but relentlessly wet from November to May.