Sit on the Right side of the plane for the best views on flights from Winnipeg to Chicago. The right side captures the most interesting geography: the Winnipeg river confluence on departure, and during the cruise the right side faces generally east toward the Great Lakes region. However the Chicago approach advantage goes left. Overall the right side wins on departure spectacle and the mid-flight view of Wisconsin's lake-dotted landscape approaching from the northwest.

During takeoff from Winnipeg International (YWG), sit on the Right side for the best views. Winnipeg's most common departure runway is 36 (northward) or 13/31. For a southbound flight to Chicago, aircraft typically depart on runway 31 or 18, then turn southeast. The right side captures downtown Winnipeg, the Red River and Assiniboine River confluence, and the city grid as you climb out heading southeast. Notable sights include: Red River and Assiniboine River confluence (The Forks), downtown Winnipeg skyline, Lake Winnipeg visible to the north on clear days, flat Manitoba agricultural grid stretching southeast.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals from the north typically use runways 10L/10R or 28L/28R depending on wind. Approaching from the northwest over the Chicago suburbs, the left side gives a clear view of Lake Michigan's shoreline, the Chicago downtown skyline, and the dense urban fabric of the north side of the city as you descend. Notable sights include: Lake Michigan shoreline and downtown Chicago skyline, Chicago's north side urban grid, O'Hare airport complex visible below on final approach, suburban Cook County sprawl.

The flight from Winnipeg International (YWG) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks southeast across the flat Red River Valley into Minnesota, crossing the Minnesota-Wisconsin border region with its glacially-formed lakes and forested terrain around the Twin Cities area to the west. Over Wisconsin, the landscape transitions from agricultural plains to the more rolling, lake-dotted terrain of the Driftless Area and glaciated Wisconsin. The Mississippi River is crossed somewhere over southern Wisconsin or northern Illinois, visible as a broad meandering ribbon. Northern Illinois farmland gives way to the expanding Chicago metropolitan sprawl on descent.