Loading map...
CLE → MDW
Which side of the plane to sit from Cleveland Hopkins International Airport (Cleveland) to Chicago Midway International Airport (Chicago)?
Right Side of the Plane
The right side of the aircraft offers the most dramatic views, including the Lake Erie coastline shortly after takeoff and the iconic Chicago skyline during the descent into Midway.
Search flights from CLE to MDW
Lake Erie Shoreline
Stunning views of the coastline and the islands of western Lake Erie shortly after takeoff.
Cedar Point
The world-famous amusement park and its towering roller coasters are often visible near Sandusky.
Detroit Skyline
On clear days, the Detroit-Windsor skyline can be seen across the lake to the north.
Chicago Skyline
Breathtaking views of the Willis Tower and downtown skyscrapers during the approach to MDW.
The right side is essential for the Chicago skyline. During the standard approach to Midway, the plane often banks over Lake Michigan, placing the Loop and Navy Pier directly in your window. Afternoon flights offer the best lighting for photography of the Chicago skyline as the sun illuminates the buildings from the west.
Book Hotels in Chicago
Cuyahoga Valley
Views of the lush, forested valley south of Cleveland immediately after departure.
Indiana Farmlands
A sprawling patchwork of agricultural fields and wind farms across Northern Indiana.
Indiana Dunes
The distinct sandy shoreline and ridges of Indiana Dunes National Park on the south end of Lake Michigan.
Gary Industrial Zone
Historic steel mills and heavy industrial infrastructure along the southern lakefront.
Choose the left side for better lighting during morning flights, as the sun will be behind you. Look for the geometric precision of the Midwestern grid system and the dense industrial history of Northwest Indiana during the final descent.
Get eSIMs for United States
Get eSIMs for United StatesDistance: 492 km (306 miles)
Approximate Flight Time: 49 min
Departure: CLE (41.4117012024, -81.8498001099)
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.