Sit on the Left side of the plane for the best views on flights from Hartford to Chicago. While the takeoff from Hartford offers pleasant river and forest views, the landing approach into Chicago provides more dramatic and visually distinctive scenery—Lake Michigan, the Chicago skyline, and the stark contrast between prairie and urban development make the left side the stronger choice for the overall flight.

During takeoff from Hartford Brainard (HFD), sit on the Right side for the best views. Right side offers views of the Connecticut River valley and the transition from coastal Connecticut toward the interior. You'll see the river's meandering path and the forested terrain that dominates central Connecticut during the westbound climb. Notable sights include: Connecticut River, Hartford city grid, Farmington River valley, forested uplands of central Connecticut.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left side provides excellent views of the Chicago metropolitan area and Lake Michigan during descent. You'll see the lake's shoreline, downtown Chicago's skyline, and the urban sprawl extending inland—particularly striking during the final approach vectors into Midway. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline, Illinois prairie and urban grid, Des Plaines River.

The flight from Hartford Brainard (HFD) to Chicago Midway International (MDW) takes Approximately 3 hours 15 minutes.

The flight path crosses central New York (Finger Lakes region visible from altitude), then transitions over Pennsylvania's ridge-and-valley terrain, crosses the Ohio River into Ohio, and continues over Indiana's relatively flat agricultural landscape. Lake Erie may be visible to the north during the New York portion. The terrain gradually flattens as you move westward from the Appalachian foothills into the Midwest plains.