While landing favors the right, the takeoff experience on the left side—with Lake Michigan and Chicago's skyline—provides more dramatic and recognizable scenery. The eastbound flight path over relatively flat terrain offers limited midpoint views, making the departure experience the stronger choice.
Flown ORD to HFD? Did we get it right?
Flight Path
Chicago to Hartford is 784 miles (1,262 km), a flight of about 2 hours 55 minutes.
The flight crosses Ohio and Pennsylvania at cruise altitude (around 30,000 feet), passing over the Appalachian foothills. Lake Erie is visible on the northern horizon during the early portion of the flight. The terrain transitions from flat Midwest plains to rolling hills as the aircraft approaches the Northeast. Few dramatic landmarks are visible at cruise altitude along this route; the landscape is primarily a patchwork of farmland, forests, and small towns.
Great circle distance and headings ›Phase by phase

Takeoff from ORD
LEFTLeft side offers views of Lake Michigan's shoreline immediately after departure, with the Chicago skyline visible in the distance. The aircraft typically climbs eastward over the lake before turning northeast toward Hartford.
Landing at HFD
RIGHTRight side provides views of the Connecticut River valley and Hartford's urban area during approach. The aircraft descends from the west, making a right turn toward Brainard Airport, giving right-side passengers clear views of the Connecticut River and downtown Hartford.
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About This Route
Which side of the plane should I sit on flying from Chicago Ohare International (ORD) to Hartford Brainard (HFD)?
Sit on the Left side of the plane for the best views on flights from Chicago to Hartford. While landing favors the right, the takeoff experience on the left side—with Lake Michigan and Chicago's skyline—provides more dramatic and recognizable scenery. The eastbound flight path over relatively flat terrain offers limited midpoint views, making the departure experience the stronger choice.
What can I see during takeoff from Chicago Ohare International in Chicago?
During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. Left side offers views of Lake Michigan's shoreline immediately after departure, with the Chicago skyline visible in the distance. The aircraft typically climbs eastward over the lake before turning northeast toward Hartford. Notable sights include: Lake Michigan, Chicago downtown skyline, Des Plaines River valley, suburban Chicago grid pattern.
What can I see when landing at Hartford Brainard in Hartford?
When landing at Hartford Brainard (HFD), sit on the Right side for the best views. Right side provides views of the Connecticut River valley and Hartford's urban area during approach. The aircraft descends from the west, making a right turn toward Brainard Airport, giving right-side passengers clear views of the Connecticut River and downtown Hartford. Notable sights include: Connecticut River, Hartford downtown district, Farmington River confluence, central Connecticut hills.
How long is the flight from Chicago to Hartford?
The flight from Chicago Ohare International (ORD) to Hartford Brainard (HFD) takes about 2 hours 55 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 Chicago to Hartford flight path pass over?
The flight crosses Ohio and Pennsylvania at cruise altitude (around 30,000 feet), passing over the Appalachian foothills. Lake Erie is visible on the northern horizon during the early portion of the flight. The terrain transitions from flat Midwest plains to rolling hills as the aircraft approaches the Northeast. Few dramatic landmarks are visible at cruise altitude along this route; the landscape is primarily a patchwork of farmland, forests, and small towns.