Sit on the Right side of the plane for the best views on flights from Madison to Chicago. The right side misses the Madison lakes on departure but captures the Chicago skyline and Lake Michigan on approach, which is the more dramatic and memorable view on this short route. The Chicago skyline visible from the right seat on descent is the standout visual of the flight.

During takeoff from Dane Co Rgnl Truax Fld (MSN), sit on the Left side for the best views. MSN typically departs runway 18 (southbound) or runway 36 (northbound). On a southbound departure toward ORD, the left (east) side gives you a clear view back over Lake Monona and Lake Mendota as the aircraft climbs and turns southeast. These two lakes flanking the Madison isthmus are immediately recognizable from low altitude. Notable sights include: Lake Mendota to the north, Lake Monona to the south of the isthmus, the Wisconsin State Capitol dome visible on the isthmus between the lakes, Lake Waubesa further south.

When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. Arrivals into ORD from the northwest on runways 10R/10L or 9R/9L have the aircraft approaching from the northwest, putting the right (south) side facing Chicago's downtown skyline and Lake Michigan. The Loop and lakefront are clearly visible on approach as the aircraft descends through 5,000-8,000 feet over the northwest suburbs. Notable sights include: Chicago Loop skyline on the horizon to the southeast, Lake Michigan shoreline visible to the east, O'Hare's runway complex below, northwest suburban sprawl of Schaumburg and Elk Grove Village in the foreground.

The flight from Dane Co Rgnl Truax Fld (MSN) to Chicago Ohare International (ORD) takes Approximately 35-45 minutes.

The flight crosses flat glaciated agricultural land of southern Wisconsin and northern Illinois — a patchwork of rectangular farm fields, small towns, and the Fox River valley. The terrain is uniformly flat with no significant topographic features. Rockford, Illinois may be visible to the right (west) side in the mid-flight portion. The landscape transitions gradually from Wisconsin farmland to the denser suburban development of the Chicago metropolitan area as you approach ORD.