Sit on the Right side of the plane for the best views on flights from Chicago to Boston. The right side wins overall. The Chicago departure view is spectacular and hard to beat — the full skyline and lakefront laid out below is one of the best urban aerial views in the country. En route, the right side also tracks closer to Lake Erie's southern shore over northern Indiana and Ohio, offering water views mid-flight. The Boston arrival on the left is excellent, but the Chicago departure on the right is the highlight of this route.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. Departing east from ORD on runways 10R/10L, the right side gives you a clear view south over downtown Chicago's skyline and the lakefront. You'll see the Willis Tower, Grant Park, and the Museum Campus laid out along Lake Michigan's shoreline as you climb out. Notable sights include: Willis Tower and downtown Chicago skyline, Lake Michigan shoreline and Navy Pier, Grant Park and Museum Campus, Midway Airport to the south.

When landing at General Edward Lawrence Logan International (BOS), sit on the Left side for the best views. Logan Airport sits on a peninsula in Boston Harbor, and most arrivals from the west use runway 04R/04L or 33L, putting the left side over the harbor and downtown Boston. The left window gives you Boston Harbor islands, the downtown skyline, and the Charles River basin as you descend. Notable sights include: Boston Harbor and its islands, Downtown Boston skyline including Prudential Tower and One International Place, Charles River and Cambridge, Cape Cod Bay visible to the south on clear days.

The flight from Chicago Ohare International (ORD) to General Edward Lawrence Logan International (BOS) takes Approximately 2 hours 15 minutes.

The flight tracks northeast over northern Indiana, then across northern Ohio near Cleveland and Lake Erie's southern shoreline, then over the Lake Erie-Lake Ontario gap near Buffalo and the southern edge of the Finger Lakes region in upstate New York, before crossing the Berkshire Hills of western Massachusetts and descending into Boston.