Sit on the Left side of the plane for the best views on flights from San Antonio to Chicago. While the takeoff offers decent Hill Country views on the right, the landing approach into Chicago on the left side provides superior scenery—Lake Michigan, the iconic skyline, and the urban grid are all visually compelling and worth the trade-off.

During takeoff from San Antonio International (SAT), sit on the Right side for the best views. Right-side seats capture San Antonio's urban sprawl and the surrounding Texas Hill Country terrain as you climb northeastward. You'll see the city grid fade into rolling hills and scattered ranch land. Notable sights include: San Antonio city center and downtown skyline, Texas Hill Country rolling terrain to the north and east, Medina River valley visible as a linear feature through the landscape.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left-side seats offer the best views during descent into Chicago. You'll see Lake Michigan's shoreline, the Chicago skyline, and the grid of neighborhoods approaching Midway from the southwest. Notable sights include: Lake Michigan's eastern shoreline and water surface, Chicago downtown skyline and Willis Tower, the grid pattern of Chicago's South Side neighborhoods, Midway International Airport runways and surrounding industrial areas.

The flight from San Antonio International (SAT) to Chicago Midway International (MDW) takes Approximately 3 hours 15 minutes.

The flight path crosses central Texas and Oklahoma, passing over the Brazos River valley, the Red River (Texas-Oklahoma border), and the Arbuckle Mountains in southern Oklahoma. Around the midpoint near the Oklahoma-Kansas border, you may see scattered lakes and prairie terrain. As you approach Illinois, the landscape flattens into agricultural plains with visible field patterns and occasional river valleys. The Illinois River and its tributaries become visible in the final hour before reaching Chicago.