Sit on the Left side of the plane for the best views on flights from Chicago to Boston. Left side wins at both ends of the flight. At departure you get the Chicago lakefront and skyline, and at arrival you get Boston Harbor and the city approach. The left side also tracks closer to Lake Erie's southern shore during cruise, offering occasional glimpses of the Great Lakes coastline.

During takeoff from Chicago Midway International (MDW), sit on the Left side for the best views. Midway's primary departure runway 31C sends aircraft northwest then curving northeast, putting the Chicago lakefront and downtown skyline on the left side. You get a clear view of the Loop, Grant Park, and Lake Michigan's shoreline as the aircraft banks right toward its eastbound heading. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Soldier Field.

When landing at General Edward Lawrence Logan International (BOS), sit on the Left side for the best views. Logan's primary arrival runways 04L/04R bring aircraft in from the southwest over Boston Harbor, putting the city of Boston, Back Bay, and the harbor islands on the left side. The approach over the water gives a clean view of the downtown skyline and the harbor before touchdown. Notable sights include: Boston Harbor and its islands, downtown Boston skyline, Back Bay and the Charles River, Logan Airport's peninsula setting.

The flight from Chicago Midway International (MDW) to General Edward Lawrence Logan International (BOS) takes Approximately 2 hours 10 minutes.

The flight tracks northeast across Indiana and Ohio, crossing over or near Cleveland and the southern shore of Lake Erie, then through upstate New York passing south of the Finger Lakes region, before crossing into New England over the Berkshire Hills of western Massachusetts and the Connecticut River valley.