Sit on the Right side of the plane for the best views on flights from Dubai to Chicago. The Chicago approach on the right side delivers the iconic Lake Michigan and Loop skyline combination, which is one of the most visually striking urban arrivals in North America. The Dubai left-side departure is excellent but the Chicago arrival edges it out for sheer visual impact.

During takeoff from Dubai International (DXB), sit on the Left side for the best views. DXB's primary departure runway 30L/30R sends aircraft northwest over the city. The left side captures the Dubai Creek, Deira district, and the older city grid before the aircraft banks over the Gulf. Right side gets desert scrub and industrial zones. Notable sights include: Dubai Creek and Deira waterfront, Downtown Dubai skyline with Burj Khalifa visible to the south, Palm Jumeirah in the distance along the coast, Persian Gulf coastline stretching northwest.

When landing at Chicago Midway International (MDW), sit on the Right side for the best views. MDW sits on Chicago's southwest side. Arrivals typically come from the southwest on runway 31C/31L heading northeast, meaning the right side faces southeast toward Lake Michigan, the Chicago Loop skyline, and the lakefront. Left side sees suburban sprawl. Notable sights include: Chicago Loop skyline with Willis Tower, Lake Michigan shoreline and lakefront parks, Chicago River corridor visible in the urban grid, Midway Airport itself visible just before touchdown.

The flight from Dubai International (DXB) to Chicago Midway International (MDW) takes Approximately 14 to 15 hours nonstop.

The route tracks northwest from Dubai over the Persian Gulf briefly, then across Iran and the Caspian Sea, over southern Russia and Ukraine, across Poland and Germany, then over the North Sea or northern UK depending on routing, across the North Atlantic, over Greenland's ice sheet and Baffin Island, then south over Hudson Bay and the Great Lakes region into Chicago. The Greenland ice cap and Hudson Bay are the most visually dramatic midpoint features, with the Caspian Sea and Black Sea visible in the earlier portion of the flight.