Sit on the Left side of the plane for the best views on flights from Nashville to Chicago. While takeoff favors the right for Nashville views, the landing approach into Midway on the left side is superior—Lake Michigan and the Chicago skyline are iconic and consistently visible, whereas the northbound cruise segment offers limited dramatic features. Left seats capture the most memorable portion of the flight.

During takeoff from Nashville International (BNA), sit on the Right side for the best views. Nashville typically departs runways 20L/20R heading north-northwest. Right-side seats offer immediate views of downtown Nashville and the Cumberland River's distinctive meanders as you climb out over the city. Notable sights include: Downtown Nashville skyline, Cumberland River with its characteristic S-curve bends, Percy Priest Lake to the east, and the rolling terrain of Middle Tennessee transitioning northward.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Chicago Midway typically uses runways 31L/31R for landing (heading west-southwest). Left-side seats provide excellent views of Lake Michigan's shoreline, the Chicago skyline, and the approach path over the city's south and west sides. Notable sights include: Lake Michigan with its distinctive bright blue-green water and Chicago shoreline, downtown Chicago skyline with Willis Tower and clustered high-rises, the grid pattern of Chicago's street system, and the industrial areas of the south side.

The flight from Nashville International (BNA) to Chicago Midway International (MDW) takes Approximately 1 hour 15 minutes.

The flight path crosses central Kentucky and southern Indiana at cruise altitude (typically 25,000-31,000 feet). Notable features include the Kentucky River valley system, the Ohio River visible as a thin line on the horizon near the Kentucky-Indiana border, and the flat agricultural plains of Indiana with scattered lakes and reservoirs. At cruise altitude these features appear as subtle terrain variations and water reflections rather than dramatic landmarks. The transition from Tennessee's rolling terrain to the flat Midwest is gradual and best appreciated from the left side as you track northwestward.