About This Route
Which side of the plane should I sit on flying from Los Cabos International (SJD) to Chicago Midway International (MDW)?
Sit on the Right side of the plane for the best views on flights from San Jose Del Cabo to Chicago. Takeoff views from the right side are substantially more dramatic—the Sierra de la Laguna and Pacific coastline provide striking topography. Landing views favor the left (Lake Michigan and Chicago skyline), but the takeoff advantage is more pronounced. Right-side seats win overall for this route.
What can I see during takeoff from Los Cabos International in San Jose Del Cabo?
During takeoff from Los Cabos International (SJD), sit on the Right side for the best views. SJD typically departs northbound on Runway 01. Right-side seats face east toward the Sierra de la Laguna mountains and the Pacific coastline, offering dramatic topography. Left seats look inland over flat desert with minimal visual interest. Notable sights include: Sierra de la Laguna (mountain range rising 6,000+ feet inland), Pacific Ocean coastline with Cabo San Lucas peninsula, Todos Santos Bay, desert plateau of Baja California Sur.
What can I see when landing at Chicago Midway International in Chicago?
When landing at Chicago Midway International (MDW), sit on the Left side for the best views. MDW approaches from the northeast on Runway 31L/31R. Left-side seats face south-southwest toward downtown Chicago and Lake Michigan. You'll see the Chicago skyline, the lake's southern shore, and the grid of neighborhoods. Right seats face the industrial southwest suburbs with less distinctive features. Notable sights include: Lake Michigan (massive freshwater body), Chicago downtown skyline and Willis Tower, Grant Park along the lakefront, residential neighborhoods of South Side Chicago.
How long is the flight from San Jose Del Cabo to Chicago?
The flight from Los Cabos International (SJD) to Chicago Midway International (MDW) takes Approximately 4 hours 15 minutes.
What does the San Jose Del Cabo to Chicago flight path pass over?
The flight path crosses the Sierra Madre Occidental mountain range in mainland Mexico (visible around 1.5 hours into flight), then traverses the high desert plateau of northern Mexico and southern United States. The Rio Grande appears as a thin line marking the US-Mexico border around 2.5 hours into flight. The Great Plains of Texas and Oklahoma dominate the midpoint, with sparse landmarks until approaching the Mississippi River valley near the end of cruise.