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SAT → MDW
Which side of the plane to sit from San Antonio International Airport (San Antonio) to Chicago Midway International Airport (Chicago)?
Right Side of the Plane
The right side is the preferred choice for this route, offering superior views of the major river systems and the world-famous Chicago skyline during the final approach into Midway.
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Mississippi River
A grand crossing of the United States' largest river system near its confluence with the Ohio River.
Shawnee Forest
Spot the unique rock formations and dense canopy of this expansive Southern Illinois forest.
Industrial Joliet
Watch active barge traffic and massive intermodal rail yards that define the region's shipping legacy.
Chicago Skyline
Experience breathtaking views of the Willis Tower and the dense skyscrapers of the Loop during descent.
Lake Michigan
The deep blue expanse of the Great Lakes comes into view as the aircraft aligns for the final runway approach.
The right side is essential for the iconic Chicago arrival; choose an afternoon flight so the sun illuminates the skyline from the west. If the flight approaches from the south, you will have a front-row seat to the city's architecture and the lakefront shoreline.
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Hill Country
View the rugged limestone terrain and suburban expansion north of San Antonio during initial climb.
Ozark Mountains
Observe the lush forested ridges and rolling highlands along the Missouri and Arkansas border.
Missouri Heartlands
Enjoy the vast geometric patterns and vibrant colors of the Midwestern agricultural landscape.
St. Louis Horizon
The urban center of St. Louis and the iconic Gateway Arch are often visible in the distance to the northeast.
Route 66 Path
Track the historic highway corridor as it winds through the rural towns of central Illinois.
Sit on the left for morning flights to keep the sun behind you for better visibility of the Ozark plateau. This side offers more consistent views of the rural landscape and is less likely to be obscured by the afternoon sun glare.
Get eSIMs for United States
Get eSIMs for United StatesDistance: 1,668 km (1,036 miles)
Approximate Flight Time: 2 hrs 13 min
Departure: SAT (29.533700942993164, -98.46980285644533)
Arrival: MDW (41.785999, -87.752403)
Route Type: Domestic
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