The left side wins narrowly thanks to the more textured Hill Country terrain visible on approach into San Antonio, since the rest of the flight over the Great Plains offers little variation on either side.
Flight Path
Flat agricultural plains of Illinois, Missouri, and Oklahoma, with the Red River marking the Texas border before the terrain transitions into the rolling Texas Hill Country near San Antonio.
Great circle distance and headings ›Phase by phase

Takeoff from ORD
RIGHTDeparting ORD southbound, the right side offers views of Chicago's southern suburbs and Lake Michigan's shoreline briefly receding behind, giving a bit more visual interest than the flat farmland on the left.
Landing at SAT
LEFTOn approach into SAT from the north, the left side reveals the Texas Hill Country's low limestone hills and green river valleys northwest of the city, more textured than the flat urban sprawl to the south seen from the right.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Chicago Ohare International (ORD) to San Antonio International (SAT)?
Sit on the Left side of the plane for the best views on flights from Chicago to San Antonio. The left side wins narrowly thanks to the more textured Hill Country terrain visible on approach into San Antonio, since the rest of the flight over the Great Plains offers little variation on either side.
What can I see during takeoff from Chicago Ohare International in Chicago?
During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. Departing ORD southbound, the right side offers views of Chicago's southern suburbs and Lake Michigan's shoreline briefly receding behind, giving a bit more visual interest than the flat farmland on the left. Notable sights include: Lake Michigan shoreline, Chicago southern suburbs, Cook County forest preserves.
What can I see when landing at San Antonio International in San Antonio?
When landing at San Antonio International (SAT), sit on the Left side for the best views. On approach into SAT from the north, the left side reveals the Texas Hill Country's low limestone hills and green river valleys northwest of the city, more textured than the flat urban sprawl to the south seen from the right. Notable sights include: Texas Hill Country foothills, Medina River valley, San Antonio northwest suburbs.
How long is the flight from Chicago to San Antonio?
The flight from Chicago Ohare International (ORD) to San Antonio International (SAT) takes 2h 40m.
What does the Chicago to San Antonio flight path pass over?
Flat agricultural plains of Illinois, Missouri, and Oklahoma, with the Red River marking the Texas border before the terrain transitions into the rolling Texas Hill Country near San Antonio.