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JAX destination photo
MDW destination photo

JAXMDW

Our Recommendation
8.7

Right Side of the Plane

The right side is the clear winner for this route, primarily due to the spectacular approach into Chicago. While the flight crosses beautiful Appalachian scenery, the highlight is the descent into Midway, which frequently offers views of the Chicago skyline, the Willis Tower, and the Lake Michigan shoreline.

Right Side Highlights
8.7
⛰️

Blue Ridge Mountains

Enjoy views of the rolling Appalachian peaks and the lush green ridges of the Tennessee Valley during the middle of the flight.

🌉

Cincinnati Waterfront

Look for the dense downtown area of Cincinnati and the numerous bridges spanning the Ohio River as you cross into the North.

🏁

Indianapolis Motor Speedway

If the flight path takes a slightly easterly track toward Chicago, look for the iconic 2.5-mile oval track north of Indianapolis.

🌃

Chicago Skyline & Loop

The 'money shot' of the trip; the Willis Tower and the dense cluster of skyscrapers in the Loop are typically visible on the right during the descent.

⛵

Lake Michigan Shoreline

See the transition from the blue waters of the lake to the industrial ports of Gary, Indiana, and the beaches of South Chicago.

The right side is essential for the Chicago arrival. For morning flights, the sun will be behind you, lighting up the skyline perfectly for photography. Aim for a seat in front of the wing to ensure your view of the mountains and the Chicago skyline is not obstructed by the engine or wing surface.

Left Side Highlights
6.2
🌳

Okefenokee National Wildlife Refuge

View the vast, dark waters and cypress forests of the massive swamp straddling the Florida-Georgia border shortly after takeoff.

🍑

Atlanta Metropolitan Area

Depending on the specific air corridor, you may see the sprawl of Atlanta and its major transportation arteries to the west.

🎸

Nashville & Cumberland River

Catch a glimpse of the bends in the Cumberland River and the outskirts of Tennessee's capital city.

🌊

Ohio River Crossing

Witness the natural border between Kentucky and Indiana as the aircraft moves into the Midwestern heartland.

🌽

The Prairie Grid

Observe the precise geometric patterns of Indiana and Illinois farmland, particularly striking during the growing season.

Sit on the left if you are flying in the late afternoon or early evening to avoid the direct glare of the setting sun. While less scenic for the Chicago arrival, this side provides better views of the intense agriculture and small-town grids of the Midwest.

Top Activities in Chicago
Route Information

Distance: 1,368 km (850 miles)

Approximate Flight Time: 1 hr 49 min

Departure: JAX (30.49410057067871, -81.68789672851562)

Arrival: MDW (41.785999, -87.752403)

Route Type: Domestic

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