Sit on the Left side of the plane for the best views on flights from Chicago to Duluth. Left side wins both ends of the flight. During the short 1.5-hour cruise at altitude over northern Wisconsin, the left side also faces generally toward the scattered lakes of the Northwoods and eventually the St. Louis River watershed, making it the consistently better seat throughout.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common departure heading on runways 10/28 or 9R/27L sends aircraft northeast or east before turning northwest toward Duluth. A left-side seat captures the Chicago skyline to the south as you climb out, with Lake Michigan's southwestern shoreline clearly visible. The dense urban grid of Chicago's North Side and the lakefront are unmistakable from 3,000-8,000 feet. Notable sights include: Chicago downtown skyline to the south, Lake Michigan southwestern shoreline, Chicago's North Shore suburbs along the lakefront, O'Hare's own massive runway complex below.

When landing at Duluth International (DLH), sit on the Left side for the best views. Duluth typically lands on runway 9 (heading east) or 27 (heading west). On an approach from the south or southwest, a left-side seat faces north toward Lake Superior's western tip, which is the defining geographic feature of Duluth — the massive lake fills the view with the city perched on the hillside above the harbor. The Duluth-Superior harbor, the aerial lift bridge area, and the dramatic bluff topography are all on the left. Notable sights include: Western tip of Lake Superior, Duluth-Superior harbor and bay, Duluth's hillside bluff rising steeply above the waterfront, the St. Louis River estuary and Wisconsin Point.

The flight from Chicago Ohare International (ORD) to Duluth International (DLH) takes Approximately 1 hour 20 minutes to 1 hour 40 minutes.

The flight tracks northwest over southern Wisconsin, crossing the Wisconsin River valley and the Chippewa River watershed. The terrain transitions from flat agricultural land around Madison's latitude to increasingly forested Northwoods terrain with hundreds of small glacial lakes visible across northern Wisconsin — the lake district around Hayward and the Chequamegon National Forest area. No major mountain ranges or dramatic topography, but the density of lakes increases noticeably as you approach Minnesota.