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BOS destination photo
ORD destination photo

BOSORD

Our Recommendation
8.5

Left Side of the Plane

The left side consistently provides the best views of the Boston harbor at takeoff and the iconic Chicago skyline during the standard approach into O'Hare over Lake Michigan.

Left Side Highlights
8.5
🏙️

Boston Harbor & City

Unrivaled views of the Financial District, Back Bay, and the Charles River immediately after departure from Logan.

🍇

Finger Lakes

Bird's-eye view of the long, narrow glacial lakes of Upstate New York, particularly Seneca and Cayuga Lakes.

🏖️

Lake Erie Coastline

Follows the southern shore of the lake, offering views of the Cleveland waterfront and the Cedar Point peninsula.

🏗️

Gary Industrial Belt

The massive scale of the steel mills and the contrast with the Indiana Dunes National Park are visible near the lake.

🏢

Chicago Skyline

On the common 'Bridgeport' approach, passengers see the Willis Tower and the dense downtown Loop from the south.

For the best arrival experience, choose a window seat on the left. When the wind is from the west, planes often fly past the city over the lake before turning back to land, providing a spectacular view of the entire skyline. In winter, this side catches the low southern sun, which is great for photography but might require a shade.

Right Side Highlights
7.8
⛰️

The Berkshires

Picturesque views of the rolling mountains and dense forests of western Massachusetts and eastern New York.

🌊

Niagara Falls

If the flight path trends slightly north, the mist and Horseshoe Falls are visible near the Buffalo area.

🏙️

Toronto Skyline

On exceptionally clear days, the CN Tower and Toronto's dense waterfront can be spotted across Lake Ontario.

🚢

Lake Michigan Crossing

A massive expanse of blue water often dotted with cargo ships and private vessels approaching the Illinois coast.

🌳

North Shore Suburbs

Beautiful views of the affluent suburbs and the 'Baha'i House of Worship' in Wilmette during the descent.

The right side is the 'Niagara Side.' Keep an eye on your flight tracker about 45-60 minutes into the flight. If the plane stays north of Lake Erie, this is your best chance to see the falls. This side also avoids direct glare from the sun on afternoon flights heading west.

Top Activities in Chicago
Route Information

Distance: 1,391 km (864 miles)

Approximate Flight Time: 1 hr 51 min

Departure: BOS (42.36429977, -71.00520325)

Arrival: ORD (41.9786, -87.9048)

Route Type: Domestic

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