St. Louis to Chicago is 258 miles (415 km), a flight of about 1 hour 20 minutes.
Both sides are fairly modest given the short, flat-terrain route, but the right side edges ahead with the Mississippi River and St. Louis skyline visible at takeoff, plus decent farmland patterns throughout — slightly more consistent scenic interest across the full flight than the left, which is only strong during the final descent into Chicago.
Flight Path
Flat Illinois farmland, scattered small towns, and the Illinois River valley are visible below during cruise, with no major mountains or coastlines along this short Midwest route
Great circle distance and headings ›Phase by phase

Takeoff from STL
RIGHTDeparting STL to the north, the right side offers views over the Mississippi River and the Illinois floodplains as the plane banks toward Chicago. The river's confluence area and downtown St. Louis with the Gateway Arch are briefly visible on this side during initial climb.

Landing at ORD
LEFTLanding at ORD typically approaches from the south or west, giving left-side passengers sweeping views of Chicago's skyline and Lake Michigan's shoreline as the plane descends. The dense grid of suburban Chicago and the lake's edge are much more visually distinct than the flat farmland on the right.
Landmarks on this routeAll landmarks →
Will your flight be in sunlight?
Pick a date and time in the Sun Map to watch the sun move across your whole flight.
About This Route
Which side of the plane should I sit on flying from Lambert St Louis International (STL) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from St. Louis to Chicago. Both sides are fairly modest given the short, flat-terrain route, but the right side edges ahead with the Mississippi River and St. Louis skyline visible at takeoff, plus decent farmland patterns throughout — slightly more consistent scenic interest across the full flight than the left, which is only strong during the final descent into Chicago.
What can I see during takeoff from Lambert St Louis International in St. Louis?
During takeoff from Lambert St Louis International (STL), sit on the Right side for the best views. Departing STL to the north, the right side offers views over the Mississippi River and the Illinois floodplains as the plane banks toward Chicago. The river's confluence area and downtown St. Louis with the Gateway Arch are briefly visible on this side during initial climb. Notable sights include: Gateway Arch, Mississippi River, downtown St. Louis skyline, Illinois farmland grid patterns.
What can I see when landing at Chicago Ohare International in Chicago?
When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Landing at ORD typically approaches from the south or west, giving left-side passengers sweeping views of Chicago's skyline and Lake Michigan's shoreline as the plane descends. The dense grid of suburban Chicago and the lake's edge are much more visually distinct than the flat farmland on the right. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline (Willis Tower, Sears Tower area), O'Hare's runway complex, Chicago suburbs grid.
How long is the flight from St. Louis to Chicago?
The flight from Lambert St Louis International (STL) to Chicago Ohare International (ORD) takes about 1 hour 20 minutes. The shortest flight path between them is 258 miles (415 km); winds and air traffic control usually add a few percent.
What does the St. Louis to Chicago flight path pass over?
Flat Illinois farmland, scattered small towns, and the Illinois River valley are visible below during cruise, with no major mountains or coastlines along this short Midwest route