Sit on the Left side of the plane for the best views on flights from Chicago to Winnipeg. Left seats capture the most dramatic scenery: Lake Michigan and Chicago's waterfront during departure, then the open prairie and occasional river valleys during cruise. Right seats offer good landing views but less compelling en route scenery.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. Left seats offer views of Lake Michigan immediately after departure, with the Chicago shoreline and downtown skyline visible during climb-out. The aircraft departs eastbound over the lake before turning northwest toward Winnipeg, so left-side passengers see the water and urban landscape most clearly. Notable sights include: Lake Michigan, Chicago downtown skyline, North Shore suburbs along the lakefront, Waukegan area to the north.

When landing at Winnipeg International (YWG), sit on the Right side for the best views. Right seats provide views of the Red River and Winnipeg's urban area during final approach. The aircraft descends from the southeast, and right-side passengers see the river valley and city layout clearly as the airport lies west of the city center. Notable sights include: Red River, Winnipeg city center, Assiniboine River confluence, prairie landscape surrounding the city.

The flight from Chicago Ohare International (ORD) to Winnipeg International (YWG) takes 2h 15m.

Lake Michigan shoreline during initial climb, transition to agricultural prairie of Illinois and Wisconsin, Fox River valley, scattered lakes in Wisconsin, eventual approach to flat prairie terrain of Manitoba with the Red River valley becoming visible 50-60 miles before Winnipeg