While takeoff offers Lake Michigan views, the landing approach to Monterey provides superior scenic value with the dramatic Pacific coastline, Monterey Bay, and Santa Lucia Mountains—iconic California geography that dominates the final descent.
Flown MDW to MRY? Did we get it right?
Flight Path
Chicago to Monterey is 1,848 miles (2,974 km), a flight of about 4 hours 15 minutes.
During cruise over central California, left-side passengers will see the Sierra Nevada range (distant, on the horizon), the Central Valley's agricultural grid, and the transition from inland terrain to coastal mountains as the flight approaches the Pacific. Right-side passengers will see less dramatic terrain—primarily the flat Central Valley and occasional reservoirs.
Great circle distance and headings ›
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Phase by phase
Takeoff from MDW
RIGHTRight-side seats offer views of Lake Michigan and the Chicago shoreline during the initial climb westward from Midway. You'll see the lake's eastern edge and downtown Chicago's skyline receding as you gain altitude.
Landing at MRY
LEFTLeft-side seats provide excellent views during the descent approach to Monterey Regional Airport. You'll see the Monterey Peninsula, Monterey Bay, and the Pacific coastline with the Santa Lucia Mountains inland—all classic California coastal scenery.
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Monterey Regional Airport (MRY)?
Sit on the Left side of the plane for the best views on flights from Chicago to Monterey. While takeoff offers Lake Michigan views, the landing approach to Monterey provides superior scenic value with the dramatic Pacific coastline, Monterey Bay, and Santa Lucia Mountains—iconic California geography that dominates the final descent.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats offer views of Lake Michigan and the Chicago shoreline during the initial climb westward from Midway. You'll see the lake's eastern edge and downtown Chicago's skyline receding as you gain altitude. Notable sights include: Lake Michigan, Chicago downtown skyline, Chicago Lakeshore, Illinois plains extending westward.
What can I see when landing at Monterey Regional Airport in Monterey?
When landing at Monterey Regional Airport (MRY), sit on the Left side for the best views. Left-side seats provide excellent views during the descent approach to Monterey Regional Airport. You'll see the Monterey Peninsula, Monterey Bay, and the Pacific coastline with the Santa Lucia Mountains inland—all classic California coastal scenery. Notable sights include: Monterey Bay, Monterey Peninsula, Pacific Ocean, Santa Lucia Mountains.
How long is the flight from Chicago to Monterey?
The flight from Chicago Midway International (MDW) to Monterey Regional Airport (MRY) takes about 4 hours 15 minutes. The shortest flight path between them is 1,848 miles (2,974 km); winds and air traffic control usually add a few percent.
What does the Chicago to Monterey flight path pass over?
During cruise over central California, left-side passengers will see the Sierra Nevada range (distant, on the horizon), the Central Valley's agricultural grid, and the transition from inland terrain to coastal mountains as the flight approaches the Pacific. Right-side passengers will see less dramatic terrain—primarily the flat Central Valley and occasional reservoirs.