Sit on the Left side of the plane for the best views on flights from Chicago to Toronto. While the takeoff offers Lake Michigan views on the right, the landing approach into Toronto provides more dramatic and sustained scenery with Lake Ontario, the Toronto waterfront, CN Tower, and the Greater Toronto Area all visible together. The left side captures the most visually distinctive part of this flight.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats offer views of Lake Michigan as the aircraft climbs northeast from Midway. You'll see the Chicago shoreline and downtown skyline receding, with the lake dominating the view during the initial climb-out. Notable sights include: Lake Michigan, Chicago downtown skyline, Indiana shoreline to the south, Des Plaines River valley.

When landing at City Centre (YTZ), sit on the Left side for the best views. Left-side seats provide excellent views during descent into Toronto. You'll see Lake Ontario in full width, the Toronto waterfront with the CN Tower visible, and the Greater Toronto Area sprawling inland. The approach path brings these features directly into view on the left side. Notable sights include: Lake Ontario, Toronto waterfront and CN Tower, Toronto Islands, Scarborough Bluffs.

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

The flight path crosses southern Ontario, passing over the agricultural regions and small towns between Lake Michigan and Lake Ontario. Notable features include the farmland and forests of southwestern Ontario, the Grand River valley, and scattered lakes. The flight typically maintains altitude around 25,000-30,000 feet over this section, making ground features appear small but the landscape's patchwork pattern of fields and woodlots is visible. No major mountain ranges are present on this route — the terrain is gently rolling to flat throughout.