Sit on the Left side of the plane for the best views on flights from Dallas-fort Worth to Chicago. Left side wins both ends of the flight. At takeoff you get the Dallas skyline and the large reservoirs north and east of the city. At landing you get the Chicago lakefront and the Loop on approach to Midway. The right side offers little of comparable interest at either end.

During takeoff from Dallas Fort Worth International (DFW), sit on the Left side for the best views. DFW typically departs northbound on runways 17L/17R or 18L/18R, meaning a left-side seat faces west toward Fort Worth and the downtown Dallas skyline sits to the left rear. As the aircraft turns northeast toward Chicago, the left side picks up the sprawling DFW metroplex, Lake Lewisville, and Lake Ray Hubbard clearly. The right side gets suburban sprawl with fewer distinguishing features. Notable sights include: Downtown Dallas skyline, Lake Lewisville to the northwest, Lake Ray Hubbard to the east of Dallas, the dense urban grid of Fort Worth.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Midway typically lands on runway 31C or 31L heading northwest, meaning the approach comes from the southeast over the South Side of Chicago. Left-side seats face south and southwest, giving a clear view of the Chicago lakefront, Grant Park, and the Loop skyline as the aircraft descends over the city grid. Right-side seats face away from the lake toward the western suburbs. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, the dense South Side street grid.

The flight from Dallas Fort Worth International (DFW) to Chicago Midway International (MDW) takes Approximately 2 hours 15 minutes.

The route tracks northeast across the Oklahoma plains, crossing the Red River shortly after departure, then over the flat agricultural patchwork of eastern Oklahoma and southern Missouri. Around the midpoint the Ozark Plateau becomes visible as gently rolling forested terrain, a noticeable contrast to the dead-flat plains on either side. The Mississippi River crossing near St. Louis is a clear landmark, with the Gateway Arch visible on clear days from the left side. North of St. Louis the route crosses the Illinois agricultural plain, a vast flat checkerboard of corn and soybean fields all the way to the Chicago suburbs.