Sit on the Left side of the plane for the best views on flights from Miami to Chicago. While the right side wins at takeoff for the Miami Beach and Biscayne Bay views, the left side delivers the superior overall experience. It picks up the Florida interior and Lake Okeechobee mid-flight, and then delivers the spectacular Chicago lakefront approach which is genuinely one of the best urban arrival views in the US. The Chicago landing view alone tips the balance.

During takeoff from Miami International (MIA), sit on the Right side for the best views. MIA typically departs east on runway 08R/09, then turns north. The right side gives you a clear view over Biscayne Bay, the Port of Miami, and downtown Miami's skyline as the aircraft banks left heading northbound. You'll see the causeway grid connecting Miami Beach to the mainland laid out clearly below. Notable sights include: Biscayne Bay, Port of Miami cruise terminals, Downtown Miami skyline, Miami Beach barrier island.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare predominantly uses runways oriented east-west, with arrivals often from the east or southeast. On approach from the south, the left side tracks over the Chicago lakefront, Grant Park, the Loop's dense skyscraper cluster, and the long straight shoreline of Lake Michigan. This is one of the most visually dramatic urban approaches in North America. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Wrigley Field neighborhood (Lakeview).

The flight from Miami International (MIA) to Chicago Ohare International (ORD) takes Approximately 3 hours.

After departing Miami, the route tracks north over the flat Florida peninsula with Lake Okeechobee visible as a large circular inland lake roughly 60 miles north of Miami. Continuing north, the route crosses central Florida, then Georgia and Tennessee, where the western edge of the Appalachian ridgelines may be faintly visible to the right on clear days. Over Kentucky and Indiana the terrain flattens into the agricultural Midwest grid, with the Ohio River crossing near Louisville visible as a broad winding river. The final descent into Chicago crosses the flat Illinois farmland before the urban sprawl of greater Chicago appears.