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STL destination photo
MDW destination photo

STLMDW

Our Recommendation
8.5

Left Side of the Plane

The left side is typically superior for this route because it offers the most iconic views of the Chicago skyline, including the Willis Tower, during the descent into Midway.

Left Side Highlights
8.5
🌊

Missouri-Mississippi Confluence

Visible shortly after takeoff from STL, witness where the Missouri River flows into the Mississippi.

🚜

Central Illinois Farmland

A vast, geometric patchwork of corn and soybean fields that define the Midwestern landscape.

🏙️

Chicago Loop

On many approach patterns to MDW, the left side provides a direct and stunning view of the Willis Tower and the downtown skyscrapers.

✈️

O'Hare Traffic

You can often spot heavy aircraft descending toward O'Hare (ORD) at different altitudes to the north.

Sit in the front half of the cabin to avoid wing obstruction. On clear days, the descent into Chicago is one of the most scenic in the US; keep your camera ready about 15 minutes before landing. Late afternoon flights are ideal as the sun will be behind you, perfectly illuminating the Chicago skyline.

Right Side Highlights
7.5
🗼

Gateway Arch

Depending on the departure runway at STL, you may get a glimpse of the Arch and downtown St. Louis to the south.

🏛️

Springfield Capitol

The dome of the Illinois State Capitol in Springfield is often visible roughly 30 minutes into the flight.

🌊

Lake Michigan Shoreline

If the plane enters a pattern over the water, the right side offers views of the Indiana Dunes and the southern lakefront.

🏟️

South Side Landmarks

Views of the Museum of Science and Industry and Guaranteed Rate Field during the final turns for landing.

The right side is best during morning flights to avoid the direct glare of the sun. Keep an eye out immediately after takeoff for the silver glint of the Gateway Arch. If the flight approaches MDW from the east over Lake Michigan, the right side provides a beautiful view of the lake's transition to the urban shoreline.

Top Activities in Chicago
Route Information

Distance: 404 km (251 miles)

Approximate Flight Time: 40 min

Departure: STL (38.748697, -90.370003)

Arrival: MDW (41.785999, -87.752403)

Route Type: Domestic

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