Sit on the Right side of the plane for the best views on flights from Boston to Chicago. The right seat wins on takeoff with the best views of Boston Harbor and the city skyline, which is the most dramatic moment of the flight. The landing view from the left is strong but Chicago's lakefront is also partially visible from the right on many approach paths. Given that the Boston departure is the more spectacular and reliable of the two, right side edges it overall.

During takeoff from General Edward Lawrence Logan International (BOS), sit on the Right side for the best views. Logan's most common departure is northeast on runway 33L/33R or east on 04R/04L, then turning west toward Chicago. A right-side seat captures Boston Harbor, the downtown skyline, and the Charles River basin as the aircraft banks left over the city. The left side faces away from the city toward the open Atlantic. Notable sights include: Boston Harbor and its islands, downtown Boston skyline including the Prudential and Hancock towers, Charles River and Cambridge, Fenway Park.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Flights from Boston typically approach O'Hare from the east or southeast, commonly landing on runways 10L/10C heading west, or 28L/28R heading east depending on wind. On an easterly approach heading west, the left side gives a clear view of Lake Michigan's southern shoreline and the Chicago downtown skyline before touchdown. The right side faces the flat suburban sprawl of Indiana and southern Cook County. Notable sights include: Lake Michigan southern shoreline, Chicago downtown skyline including Willis Tower and the lakefront, Wrigley Field area in Lincoln Park, the grid of Chicago's street system.

The flight from General Edward Lawrence Logan International (BOS) to Chicago Ohare International (ORD) takes Approximately 2 hours 30 minutes to 2 hours 50 minutes.

The flight tracks roughly along the 42nd parallel west across Massachusetts, then over the Berkshire Hills of western Massachusetts, the Hudson Valley in upstate New York, then across the flat agricultural plains of central New York state and northern Pennsylvania, skirting south of Lake Erie, crossing northern Indiana farmland before descending into Chicago. The Berkshires are visible early in the flight as low rolling forested ridges. Lake Erie may be glimpsed to the north depending on exact routing. The terrain flattens dramatically after crossing into Ohio and Indiana, becoming a vast patchwork of rectangular farm fields all the way to Chicago.