While the left side dominates the departure with alpine scenery, the right side captures the more sustained visual interest during descent and landing with Lake Michigan and Chicago's urban landscape. For a full flight experience, right wins the overall recommendation.
Flown ASE to ORD? Did we get it right?
Flight Path
Aspen to Chicago is 1,011 miles (1,627 km), a flight of about 2 hours 40 minutes.
The flight path crosses the Rocky Mountain Front near the Wyoming-Colorado border, then transitions over the High Plains of eastern Colorado and western Kansas. Notable midpoint features include the South Platte River valley, the Colorado plains, and the gradual descent into the Mississippi River basin. The landscape shifts from high-altitude mountains to rolling prairie to flat agricultural plains, with occasional river valleys visible. No major mountain ranges are crossed after leaving the Rockies; the remainder is predominantly plains and agricultural terrain with scattered lakes and river systems.
Great circle distance and headings ›Phase by phase
Takeoff from ASE
LEFTLeft side captures the Elk Mountains and Maroon Bells immediately after departure, with the Roaring Fork Valley visible below. The eastbound climb-out over these peaks provides dramatic alpine scenery within the first 10 minutes of flight.

Landing at ORD
RIGHTRight side offers views of Lake Michigan and the Chicago shoreline during the final approach corridor. Descending from the west, the right window frames the lakefront, downtown Chicago's skyline, and the transition from prairie to urban development.
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About This Route
Which side of the plane should I sit on flying from Aspen-Pitkin County Airport (Sardy Field) (ASE) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from Aspen to Chicago. While the left side dominates the departure with alpine scenery, the right side captures the more sustained visual interest during descent and landing with Lake Michigan and Chicago's urban landscape. For a full flight experience, right wins the overall recommendation.
What can I see during takeoff from Aspen-Pitkin County Airport (Sardy Field) in Aspen?
During takeoff from Aspen-Pitkin County Airport (Sardy Field) (ASE), sit on the Left side for the best views. Left side captures the Elk Mountains and Maroon Bells immediately after departure, with the Roaring Fork Valley visible below. The eastbound climb-out over these peaks provides dramatic alpine scenery within the first 10 minutes of flight. Notable sights include: Elk Mountains, Maroon Bells, Roaring Fork Valley, Castle Peak.
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. Right side offers views of Lake Michigan and the Chicago shoreline during the final approach corridor. Descending from the west, the right window frames the lakefront, downtown Chicago's skyline, and the transition from prairie to urban development. Notable sights include: Lake Michigan, Chicago downtown skyline, Illinois prairie, Des Plaines River.
How long is the flight from Aspen to Chicago?
The flight from Aspen-Pitkin County Airport (Sardy Field) (ASE) to Chicago Ohare International (ORD) takes about 2 hours 40 minutes. The shortest flight path between them is 1,011 miles (1,627 km); winds and air traffic control usually add a few percent.
What does the Aspen to Chicago flight path pass over?
The flight path crosses the Rocky Mountain Front near the Wyoming-Colorado border, then transitions over the High Plains of eastern Colorado and western Kansas. Notable midpoint features include the South Platte River valley, the Colorado plains, and the gradual descent into the Mississippi River basin. The landscape shifts from high-altitude mountains to rolling prairie to flat agricultural plains, with occasional river valleys visible. No major mountain ranges are crossed after leaving the Rockies; the remainder is predominantly plains and agricultural terrain with scattered lakes and river systems.