Route notes
Why this routing works
This is a compact one-week multi-stop itinerary that moves in a clear sequence from New York City to Montreal, then Toronto, then back into the U.S. via Detroit, finishing in Chicago. With short stays of 2 nights, 1 night, and 1 night, the routing is built around steady onward movement rather than long stopovers.
Because the trip crosses the U.S.-Canada border more than once, keeping the cities in this order helps avoid unnecessary backtracking while linking each stop into a single ticketed plan. That can be useful for managing several flights in a short timeframe, especially when the whole trip is structured within one week.
In economy class, this route is positioned as a short-format multi-city ticket rather than a round-the-world trip, with a sold price range of $591 to $901. September timing falls in the July-September season window, making this a practical example of a regional North America itinerary with multiple brief urban stops.