Sit on the Left side of the plane for the best views on flights from Duluth to Chicago. The left side delivers the best views at both ends of the flight — Lake Superior and the Duluth harbor on departure, and the Chicago skyline and Lake Michigan on approach. The right side offers mostly flat Wisconsin and Illinois agricultural terrain throughout the cruise portion with no comparable landmarks.

During takeoff from Duluth International (DLH), sit on the Left side for the best views. Duluth typically departs runway 09 heading east or runway 27 heading west. On a southbound departure toward Chicago, aircraft generally turn south, putting Lake Superior and the Duluth harbor on the left (east) side. The vast expanse of Lake Superior dominates the view, with the Duluth-Superior harbor and the iconic Aerial Lift Bridge visible during the initial climb. Notable sights include: Lake Superior open water, Duluth-Superior harbor and ship canal, Park Point barrier spit, Wisconsin's Bayfield Peninsula across the lake.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals from the north typically use runways oriented east-west or northwest-southeast, with final approach often from the north or northwest. On approach from the Duluth direction, the left side faces east toward downtown Chicago, Lake Michigan's shoreline, and the city grid — the most visually compelling urban geography in the Midwest. Notable sights include: Downtown Chicago skyline, Lake Michigan shoreline, Chicago River grid, O'Hare airport complex sprawl.

The flight from Duluth International (DLH) to Chicago Ohare International (ORD) takes Approximately 1 hour 15 minutes to 1 hour 30 minutes.

The flight tracks roughly south-southwest over northern Wisconsin's lake-dotted forested terrain, then crosses the agricultural flatlands of central Wisconsin near Wausau and Rhinelander. The Wisconsin River valley is visible below around the midpoint. Further south the terrain transitions to the flat Illinois prairie north of Rockford, with the Fox River valley appearing before the Chicago suburban sprawl begins.