Sit on the Right side of the plane for the best views on flights from Toronto to Chicago. The right side delivers the dramatic Toronto harbour and skyline departure, and while it misses the Chicago skyline on landing, the takeoff view from Billy Bishop is genuinely spectacular and hard to beat. Left side wins landing but the departure view on the right is the highlight of this short flight.

During takeoff from City Centre (YTZ), sit on the Right side for the best views. Billy Bishop (YTZ) sits on the Toronto Islands, so takeoff on runway 26 heads west over the harbour. The right side gives you a clear look back at downtown Toronto's skyline, the CN Tower, and the full sweep of Lake Ontario's northern shoreline. Left side faces the lake with less to see. Notable sights include: CN Tower and downtown Toronto skyline, Toronto Harbour and ferry docks, Toronto Islands below, Lake Ontario shoreline stretching east.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common landing approach from the east uses runways oriented roughly east-west (runways 10/28 or 9R/27L). Coming in from the east, the left side faces south toward the Chicago skyline, which is clearly visible on approach from about 20-30 miles out. The right side faces north toward suburban sprawl with little of note. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock) visible to the south, Lake Michigan shoreline and lakefront, suburban Cook County grid, O'Hare airport complex on final.

The flight from City Centre (YTZ) to Chicago Ohare International (ORD) takes Approximately 1 hour to 1 hour 15 minutes.

The flight crosses Lake Ontario briefly after departure, then tracks southwest over the flat agricultural plains of southern Ontario near Hamilton and Brantford, crosses into the United States over the Lake Erie shoreline near Buffalo or Erie, then continues over the flat farmland of northern Indiana before entering Illinois airspace. No significant terrain changes — the entire mid-flight is low-relief agricultural land with occasional small cities and highway grids visible below.