Loading map...
SJC → MDW
Which side of the plane to sit from Norman Y. Mineta San Jose International Airport (San Jose) to Chicago Midway International Airport (Chicago)?
Left Side of the Plane
The left side provides the most iconic views on this transcontinental route, including the northern Sierra Nevada, the Great Salt Lake, and the world-famous Chicago skyline during the final approach into Midway.
Search flights from SJC to MDW
Sierra Nevada Range
Spectacular views of snow-capped peaks and the Tahoe National Forest shortly after departure.
Great Salt Lake
The northern path offers a direct look at the shimmering turquoise and silver expanses of Utah's inland sea.
Rocky Mountain National Park
View the rugged alpine tundra and high peaks of the Colorado Rockies as you cross the Continental Divide.
Great Plains Patchwork
The intricate geometric patterns of Nebraska and Iowa farmlands create a stunning aerial quilt.
Chicago Skyline
On many standard approaches to MDW, the Willis Tower and downtown skyscrapers are visible out the left window.
Book a seat on the left (Port) side for the highest probability of seeing the Chicago skyline during descent. For morning flights, this side faces north, providing better lighting for photography as the sun will be on the opposite side of the aircraft. Keep your camera ready about 15-20 minutes before landing for the best city views.
Get eSIMs for United States
Get eSIMs for United States
High Desert Basins
Dramatic views of the Nevada desert's 'Basin and Range' topography with unique geological formations.
Southern Rockies
View the southern expanses of the Colorado mountains and the urban sprawl of the Denver metro area.
Missouri River
Witness the massive, winding silver ribbon of the Missouri River as it snakes through the Midwest.
Lake Michigan Shoreline
If the flight enters via a southern pattern, you will see the industrial coastlines and sandy dunes of Northwest Indiana.
The right side is excellent for observing the vastness of the American desert and the transition to the fertile Midwest. However, be aware that on eastbound flights, this side will be directly exposed to the sun, which can cause significant glare and heat. Use a polarizing filter if taking photos to cut through the atmospheric haze over the plains.
Book Hotels in ChicagoDistance: 2,950 km (1,833 miles)
Approximate Flight Time: 3 hrs 56 min
Departure: SJC (37.362598, -121.929001)
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.