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YTZ → MDW
Which side of the plane to sit from Billy Bishop Toronto City Centre Airport (Toronto) to Chicago Midway International Airport (Chicago)?
Right Side of the Plane
While both sides offer excellent views of Toronto upon departure, the Right Side is the clear winner for its iconic, close-up panoramic views of the Chicago skyline during the standard approach into Midway.
Search flights from YTZ to MDW
Toronto Waterfront
A beautiful view of the Lake Ontario shoreline and the Harbourfront area during initial climb.
Ontario Farmlands
The geometric patchwork of Southwestern Ontario's agricultural heartland between Hamilton and London.
Ann Arbor Area
Fly past the University of Michigan campus and the rolling terrain of southern Michigan.
Chicago Loop Skyline
The premier view of the Willis Tower, Navy Pier, and the famous Chicago lakefront during the base leg turn.
Architectural Tour
A close-up look at the dense high-rises and the Chicago River as the plane lines up for the final approach.
The right side is essential for the 'Chicago Experience.' As flights typically approach Midway from the east, the plane often performs a U-turn over Lake Michigan, placing the entire Chicago skyline directly outside your window. Choose a window seat forward of the wing for the most unobstructed photography of the skyscrapers. This view is spectacular both in daylight and at night when the city is illuminated.
Book Hotels in ChicagoToronto City Core
Unmatched views of the CN Tower and the dense Financial District immediately after takeoff from the island.
Lake Erie Shoreline
Aerial perspective of the northern coast of Lake Erie and the Long Point peninsula.
Detroit-Windsor Border
Clear view of the Ambassador Bridge and the urban sprawl of Windsor and Detroit to the south.
Indiana Dunes
The unique sand dunes and industrial steel mills of the southern Lake Michigan shoreline.
South Side Chicago
Bird's eye view of Guaranteed Rate Field and the historic neighborhoods of Chicago's South Side.
Sit on the left for the best view of the CN Tower during departure from YTZ, especially if taking off to the west. On evening flights, this side catches the glow of the sunset over the industrial landscapes of northern Indiana. Avoid seats over the wing to ensure a clear view of the ground during the low-altitude cruise characteristic of this regional route.
Get eSIMs for Canada
Get eSIMs for United StatesDistance: 712 km (442 miles)
Approximate Flight Time: 1 hr 11 min
Departure: YTZ (43.627499, -79.396202)
Arrival: MDW (41.785999, -87.752403)
Route Type: International
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