The right side offers a mild edge with the Connecticut River valley and Hartford skyline at departure, glimpses of the Finger Lakes and Lake Erie shoreline during cruise, and a Chicago skyline/lakefront view on arrival, while the left side sees mostly featureless Pennsylvania and Ohio farmland.
Flown HFD to ORD? Did we get it right?
Flight Path
Hartford to Chicago is 784 miles (1,262 km), a flight of about 1 hour 50 minutes.
The route passes near the Catskills and Finger Lakes region of New York, then crosses the southern shore of Lake Erie before descending into the flat farmland of northern Ohio and Indiana approaching Chicago.
Great circle distance and headings ›Phase by phase
Takeoff from HFD
RIGHTDeparting HFD on runway 2 with a turn to the west puts the Connecticut River valley and downtown Hartford's small skyline on the right side as the aircraft climbs out and banks toward the northwest.

Landing at ORD
RIGHTArrivals into ORD from the east commonly cross over or near Lake Michigan before turning onto the west-facing runways, giving right-side passengers a view of the Chicago skyline and lakefront during the descent and turn.
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About This Route
Which side of the plane should I sit on flying from Hartford Brainard (HFD) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from Hartford to Chicago. The right side offers a mild edge with the Connecticut River valley and Hartford skyline at departure, glimpses of the Finger Lakes and Lake Erie shoreline during cruise, and a Chicago skyline/lakefront view on arrival, while the left side sees mostly featureless Pennsylvania and Ohio farmland.
What can I see during takeoff from Hartford Brainard in Hartford?
During takeoff from Hartford Brainard (HFD), sit on the Right side for the best views. Departing HFD on runway 2 with a turn to the west puts the Connecticut River valley and downtown Hartford's small skyline on the right side as the aircraft climbs out and banks toward the northwest. Notable sights include: Connecticut River, downtown Hartford skyline, rolling Connecticut hills.
What can I see when landing at Chicago Ohare International in Chicago?
When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. Arrivals into ORD from the east commonly cross over or near Lake Michigan before turning onto the west-facing runways, giving right-side passengers a view of the Chicago skyline and lakefront during the descent and turn. Notable sights include: Lake Michigan shoreline, Chicago skyline (Willis Tower, Sears Tower area), Navy Pier, Chicago's grid of suburbs.
How long is the flight from Hartford to Chicago?
The flight from Hartford Brainard (HFD) to Chicago Ohare International (ORD) takes about 1 hour 50 minutes. The shortest flight path between them is 784 miles (1,262 km); winds and air traffic control usually add a few percent.
What does the Hartford to Chicago flight path pass over?
The route passes near the Catskills and Finger Lakes region of New York, then crosses the southern shore of Lake Erie before descending into the flat farmland of northern Ohio and Indiana approaching Chicago.