Sit on the Left side of the plane for the best views on flights from Chicago to Jacksonville. The left seat delivers the more dramatic single moment of the flight — the Chicago skyline and Lake Michigan on departure — which outweighs the Jacksonville arrival views. The mid-flight path over Kentucky and Tennessee offers little distinctive scenery from either side, so the takeoff experience tips the balance to the left.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common departure heading is east or southeast on runways 10/28 or 9R/27L. A left (north) seat gives you a clear view back over the Chicago skyline as you climb out, with Lake Michigan's shoreline stretching to the northeast. The downtown Loop and lakefront are unmistakable from this angle. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Navy Pier, Grant Park and Museum Campus.

When landing at Jacksonville International (JAX), sit on the Right side for the best views. Jacksonville International sits northwest of the city, and aircraft typically approach from the north or northwest on runway 07/25 or 14/32. A right (south) seat on approach gives you views of the St. Johns River winding through Jacksonville and the Atlantic coastline to the east. The river's broad curves and the city's bridges are clearly visible on descent. Notable sights include: St. Johns River and its downtown bridges, Jacksonville Beach and Atlantic coastline, Intracoastal Waterway, downtown Jacksonville.

The flight from Chicago Ohare International (ORD) to Jacksonville International (JAX) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks southeast over Indiana farmland, then crosses Louisville and the Ohio River valley in Kentucky, continues over the Cumberland Plateau in Tennessee, crosses the Appalachian foothills in northern Georgia, then descends over the flat coastal plain of southeast Georgia and northeast Florida before reaching Jacksonville. The Tennessee River system and its reservoirs may be visible in the middle portion of the flight.