Loading map...

PIT destination photo
MDW destination photo

PITMDW

Our Recommendation
8.5

Right Side of the Plane

The right side is significantly superior for this route because it offers a panoramic view of the Chicago skyline and the Lake Michigan shoreline during the final approach into Midway.

Right Side Highlights
8.5
🏙️

Pittsburgh Skyline

Occasional views of the 'Golden Triangle' and the confluence of the three rivers shortly after takeoff.

🌊

Lake Michigan Coastline

The dramatic transition from the deep blue of the lake to the urban sprawl of the Chicago metropolitan area.

🏙️

Chicago Downtown

World-class views of the Willis Tower, the Loop, and the dense cluster of skyscrapers during the final descent.

🎡

Navy Pier

The iconic pier and Ferris wheel are often visible jutting into the lake just north of the approach path.

🏟️

Soldier Field

Clear views of the historic stadium and the Museum Campus along the lakefront.

This is the 'money side' for photographers. For the best view of the Chicago skyline, try to book a seat in front of the wing. If flying at sunset, the skyscrapers are often silhouetted against a vibrant sky, though reflections on the window can be tricky.

Left Side Highlights
6.2
🏞️

Ohio River Valley

Aerial views of the winding Ohio River as the plane departs western Pennsylvania and enters Ohio.

🚜

Midwestern Heartland

A vast 'patchwork quilt' of geometric agricultural fields across central Indiana.

🏭

Gary Industrial Belt

Intriguing views of the massive steel mills and industrial complexes along the southern tip of Lake Michigan.

Choose this side during mid-day flights to avoid the harsh southern sun. It offers a great perspective on the industrial history of the Great Lakes region during the descent, especially the scale of the shipping ports in Northwest Indiana.

Top Activities in Chicago
Route Information

Distance: 646 km (401 miles)

Approximate Flight Time: 1 hr 5 min

Departure: PIT (40.49150085, -80.23290253)

Arrival: MDW (41.785999, -87.752403)

Route Type: Domestic

Thank you for booking your travels through our travel partners. The commissions from your bookings keep this site running.