Loading map...
MDW → GSP
Which side of the plane to sit from Chicago Midway International Airport (Chicago) to Greenville Spartanburg International Airport (Greenville)?
Left Side of the Plane
The left side provides the most iconic views, starting with a potential vista of the Chicago skyline and Lake Michigan upon departure, followed by the dramatic descent over the Blue Ridge Escarpment into the Carolinas.
Search flights from MDW to GSP
Chicago Skyline
A stunning view of the Willis Tower and the Lake Michigan shoreline shortly after taking off from Midway.
Ohio River Crossing
The serpentine border between the Midwest and the South, often visible near the Indiana and Kentucky line.
Blue Ridge Mountains
The beautiful, hazy ridges of the southern Appalachians as you begin your descent into South Carolina.
Spartanburg Hub
Aerial views of the textile and automotive industrial corridor that defines the Upstate South Carolina region.
For the best views of the Chicago skyline, aim for an afternoon flight when the sun illuminates the buildings from the west. If the flight departs to the north or east, the left side is essential for seeing the downtown 'Loop' area. In the morning, be prepared for some glare as you face the sun while heading southeast.
Get eSIMs for United States
Get eSIMs for United States
Midwestern Grid
The distinct geometric patterns of Illinois and Indiana farmland stretching toward the horizon.
Daniel Boone National Forest
Vast, dense forest cover and rugged plateau terrain through eastern Kentucky.
Great Smoky Mountains
A distant look at the highest peaks of the Appalachian range visible to the south during the cruise.
Lake Keowee
The bright blue waters and winding shores of this large reservoir located just west of the flight path during descent.
The right side is excellent for afternoon flights to avoid direct sunlight and enjoy the high-contrast shadows over the Appalachian ridges. It offers a more consistent view of the deep wilderness areas of Kentucky and Tennessee. Look for the changing colors of the foliage if traveling during late October.
Book Hotels in GreenvilleDistance: 905 km (562 miles)
Approximate Flight Time: 1 hr 31 min
Departure: MDW (41.785999, -87.752403)
Arrival: GSP (34.895698547399995, -82.2189025879)
Route Type: Domestic
Thank you for booking your travels through our travel partners. The commissions from your bookings keep this site running.