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MDW → BOS
Which side of the plane to sit from Chicago Midway International Airport (Chicago) to General Edward Lawrence Logan International Airport (Boston)?
Right Side of the Plane
The right side offers a superior sequence of geographic landmarks, including the best vantage point for Niagara Falls, the iconic Finger Lakes region, and the Boston city skyline during standard landing patterns.
Indiana Dunes
The unique sandy landscape of the Indiana Dunes National Park along the southern tip of Lake Michigan.
Niagara Falls
A spectacular bird's-eye view of the Horseshoe and American Falls as the flight path crosses into New York.
Finger Lakes
The striking, elongated glacial lakes of central New York, including Cayuga and Seneca Lakes.
Quabbin Reservoir
Massachusetts' largest body of water, surrounded by pristine forest, visible shortly before beginning the final approach.
Boston Financial District
A close-up view of Boston's skyscrapers and the Charles River when arriving via the standard western approach.
The right side is essential for spotting Niagara Falls, which usually appears about halfway through the flight. If you are flying in the late afternoon, this side will catch the golden hour light over the Finger Lakes and the Catskills, though you may need to lower your window shade if the sun is too direct.
Chicago Skyline
Unparalleled views of the Willis Tower and the downtown Loop immediately following departure from Midway.
Lake Michigan Coast
Expansive views of the deep blue water and the western Michigan shoreline as the plane climbs to cruising altitude.
Detroit Metro
Visuals of the Detroit River, the Ambassador Bridge, and the urban layout of the Motor City.
Adirondack Mountains
Views of the high peaks and dense wilderness of northern New York state to the north.
Boston Harbor Islands
A scenic overlook of the historic harbor islands and the Atlantic coastline during the final descent into Logan.
Sit on the left for the most dramatic views of the Chicago skyline during takeoff, especially on clear mornings. This side also avoids direct southern sunlight for much of the eastbound journey, reducing glare for photography. Look out for the Detroit area roughly 35-45 minutes into the flight.
Distance: 1,382 km (859 miles)
Approximate Flight Time: 1 hr 51 min
Departure: MDW (41.785999, -87.752403)
Arrival: BOS (42.36429977, -71.00520325)
Route Type: Domestic
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