MRYMDWMonterey to ChicagoMonterey Regional AirporttoChicago Midway International

Sit on the right side from Monterey to Chicago

Reverse

Which side of the plane?

Pick the window seat with the view. 13,500 routes answered — landmarks, coastlines and cities, wing by wing.

Flight time4h 45m
Distance
Heading
Best side
RightMostly right

While the takeoff offers scenic coastal views on the left, the landing approach into Chicago provides more dramatic and sustained visual interest with the Lake Michigan shoreline and downtown skyline. Right-side seats capture the most iconic urban scenery of the flight.

Takeoff · MRYLeftMonterey Bay, Santa Lucia Mountains
Landing · MDWRightLake Michigan, Chicago downtown skyline

Flight Path

Flight path overview

The flight path crosses the Sierra Nevada mountains (visible during climb-out on the right), then traverses the Central Valley of California with its agricultural grid patterns, continues over the Great Basin and Rocky Mountains (Utah/Colorado region with high desert plateaus and mountain ranges), crosses the Great Plains of Kansas and Missouri with their flat, patchwork farmland, and finally approaches the Mississippi River valley before reaching Chicago.

Phase by phase

Takeoff from

Landing at

Will your flight be in sunlight?

See exactly which side of the plane gets sun and shade at your departure time.

About This Route

Which side of the plane should I sit on flying from Monterey Regional Airport (MRY) to Chicago Midway International (MDW)?

Sit on the Right side of the plane for the best views on flights from Monterey to Chicago. While the takeoff offers scenic coastal views on the left, the landing approach into Chicago provides more dramatic and sustained visual interest with the Lake Michigan shoreline and downtown skyline. Right-side seats capture the most iconic urban scenery of the flight.

What can I see during takeoff from Monterey Regional Airport in Monterey?

During takeoff from Monterey Regional Airport (MRY), sit on the Left side for the best views. Left seats offer immediate views of the Monterey Peninsula coastline, Monterey Bay, and the Santa Lucia Mountains rising inland. The climb-out heads northeast, so left-side passengers see the dramatic rocky coast and bay waters before turning toward the Central Valley. Notable sights include: Monterey Bay, Santa Lucia Mountains, Point Lobos, Carmel-by-the-Sea coastline.

What can I see when landing at Chicago Midway International in Chicago?

When landing at Chicago Midway International (MDW), sit on the Right side for the best views. Right seats provide excellent views during the descent into Chicago Midway. The approach from the west crosses Lake Michigan's eastern shoreline, and right-side passengers see the Chicago skyline, downtown high-rises, and the lakefront before touchdown. The descent path offers clear sightlines to the urban grid and water features. Notable sights include: Lake Michigan, Chicago downtown skyline, Chicago Lakeshore, Midway Airport grounds.

How long is the flight from Monterey to Chicago?

The flight from Monterey Regional Airport (MRY) to Chicago Midway International (MDW) takes 4h 45m.

What does the Monterey to Chicago flight path pass over?

The flight path crosses the Sierra Nevada mountains (visible during climb-out on the right), then traverses the Central Valley of California with its agricultural grid patterns, continues over the Great Basin and Rocky Mountains (Utah/Colorado region with high desert plateaus and mountain ranges), crosses the Great Plains of Kansas and Missouri with their flat, patchwork farmland, and finally approaches the Mississippi River valley before reaching Chicago.