Sit on the Left side of the plane for the best views on flights from Chicago to Madison. The left side misses the best of the Chicago departure but wins decisively on landing with the spectacular Madison lakes and Capitol view. Since the flight is short — under 30 minutes — the landing approach scenery carries significant weight, and the Madison isthmus with two lakes is genuinely one of the more striking urban aerial views in the Midwest.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. ORD's most common westbound departures (runways 10L/10C heading east, or 27L/27R heading west) mean a westbound departure toward Madison puts the right side facing south toward Chicago's downtown skyline and the southern suburbs. On a northwest departure heading, the right side catches Lake Michigan and the Chicago lakefront as the aircraft banks left toward Madison. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, O'Hare's distinctive runway complex below, Des Plaines River corridor.

When landing at Dane Co Rgnl Truax Fld (MSN), sit on the Left side for the best views. MSN typically uses runways 18/36 or 03/21. On a southerly approach to runway 18, or a northeast approach to runway 03, the left side faces west and northwest toward Lake Mendota and Lake Monona — Madison's most visually distinctive features — along with the Wisconsin State Capitol dome visible on the isthmus between the two lakes. Notable sights include: Lake Mendota, Lake Monona, Madison isthmus with Wisconsin State Capitol dome, University of Wisconsin campus on Lake Mendota's south shore.

The flight from Chicago Ohare International (ORD) to Dane Co Rgnl Truax Fld (MSN) takes Approximately 25-35 minutes.

The flight crosses the flat agricultural landscape of northern Illinois and southern Wisconsin — primarily corn and soybean fields in a rectilinear township grid. The Fox River valley is crossed shortly after departure. The Rock River corridor appears in the middle portion of the route near Rockford's southern suburbs. Southern Wisconsin's gently rolling terrain with scattered glacial lakes becomes visible as the aircraft begins descent toward Madison.