Loading map...
MDW → SDF
Which side of the plane to sit from Chicago Midway International Airport (Chicago) to Louisville International Standiford Field (Louisville)?
Left Side of the Plane
The left side offers a superior perspective of the Chicago skyline and Lake Michigan shoreline upon departure, followed by better views of Indianapolis and the dramatic bend of the Ohio River during the descent into Louisville.
Search flights from MDW to SDF
Chicago Skyline
Panoramic views of the Willis Tower and lakefront skyscrapers shortly after takeoff from Midway.
Lake Michigan Southern Tip
The industrial shoreline of Northwest Indiana and the vast blue expanse of the Great Lake.
Indianapolis Skyline
Mid-flight views of the Indiana State Capitol and the downtown high-rises as the plane tracks south.
Ohio River
The wide, winding river that forms the natural border between Indiana and Kentucky.
Jefferson Memorial Forest
Lush green canopy visible on the final approach into the Louisville area.
Book an early morning flight for the best lighting on the Chicago skyline without solar glare. On the descent, keep your eyes peeled for the Big Four Bridge crossing the Ohio River. If the flight departs to the North, the left side provides the iconic 'loop' view of the city.
Get eSIMs for United States
Get eSIMs for United States
Midwestern Patchwork
Classic grid-patterned Indiana farmland featuring a tapestry of corn and soybean fields.
Fowler Ridge Wind Farm
Massive clusters of white wind turbines dotting the landscape in central Indiana.
Churchill Downs
The legendary home of the Kentucky Derby and its twin spires, visible just minutes before touchdown.
Suburban Sprawl
The western suburbs of both Chicago and Indianapolis, showcasing late-20th-century residential development.
Choose this side for sunset flights to enjoy the vibrant colors over the rural landscape. Look out for the University of Louisville campus and the iconic racetrack shortly before landing. This side typically stays cooler during afternoon flights as it faces away from the direct sun.
Book Hotels in LouisvilleDistance: 437 km (272 miles)
Approximate Flight Time: 44 min
Departure: MDW (41.785999, -87.752403)
Arrival: SDF (38.1744, -85.736)
Route Type: Domestic
Thank you for booking your travels through our travel partners. The commissions from your bookings keep this site running.