Sit on the Left side of the plane for the best views on flights from Hartford to Chicago. The left side wins at both ends of this westbound flight. Over the mid-flight cruise, the left side also faces slightly more southward, keeping the Great Lakes region and any visible terrain features on that side. It is the clear choice for the full journey.

During takeoff from Hartford Brainard (HFD), sit on the Left side for the best views. Hartford Brainard typically departs runway 20 (southbound) or runway 2 (northbound). On a westbound departure to ORD, the aircraft will bank left heading northwest, putting the Connecticut River valley and downtown Hartford on the left side. The left seat also captures the initial climb over the river and the broader Connecticut landscape as the aircraft turns west. Notable sights include: Connecticut River below Hartford, downtown Hartford skyline, Farmington River valley to the northwest, Lake Compounce area to the west.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals from the east typically use runways oriented east-west (runway 10/28 or 9R/27L). On approach from the east, the left side faces south toward downtown Chicago, Lake Michigan's southern shoreline, and the city grid. The left seat gives a clear view of the Chicago skyline and the lakefront as the aircraft descends over the western suburbs. Notable sights include: Downtown Chicago skyline and Willis Tower, Lake Michigan southern shoreline, Chicago's street grid and urban density, O'Hare's runway complex visible on final approach.

The flight from Hartford Brainard (HFD) to Chicago Ohare International (ORD) takes Approximately 1 hour 45 minutes to 2 hours.

The flight crosses upstate New York's Catskill foothills, then the flat agricultural plains of central New York and northern Pennsylvania, before entering the remarkably flat terrain of northern Indiana and Illinois. The southern shore of Lake Erie may be faintly visible to the north in clear conditions near the New York-Pennsylvania border. The Appalachian ridgelines are largely avoided on this northern routing. The dominant mid-flight feature is the transition from rolling northeastern terrain to the dead-flat Midwest corn and soybean grid, visible clearly from altitude.