Sit on the Right side of the plane for the best views on flights from Chicago to Anchorage. While left side wins at takeoff for the Chicago skyline, the right side delivers the more dramatic sustained scenery: the Canadian Rockies visible in the middle of the flight and the stunning Chugach Mountain approach into Anchorage make right the better overall choice for the full journey.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD departures heading northwest on runways 10/28 or 9R/27L typically bank left after takeoff, giving left-side passengers a clear view back over downtown Chicago and Lake Michigan. The Chicago skyline with the Willis Tower and the lakefront are unmistakable from this angle during climb-out. Notable sights include: Chicago downtown skyline, Lake Michigan shoreline, Grant Park and Museum Campus, O'Hare airport layout below.

When landing at Ted Stevens Anchorage International (ANC), sit on the Right side for the best views. Anchorage approaches typically come in from the northeast over Cook Inlet on runways 06/24 or 07R/25L. Right-side passengers get the best view of the Chugach Mountains rising dramatically east of the city, while left-side passengers look out over Cook Inlet and the Kenai Peninsula across the water. Notable sights include: Chugach Mountains, Cook Inlet, Knik Arm, downtown Anchorage grid.

The flight from Chicago Ohare International (ORD) to Ted Stevens Anchorage International (ANC) takes Approximately 7 to 8 hours.

The flight tracks northwest over Wisconsin and Minnesota, then crosses the Canadian border over Manitoba or Saskatchewan. The route passes over the boreal forests and lake-dotted Canadian Shield, then crosses the Canadian Rockies and Coast Mountains of British Columbia and Yukon — including the St. Elias Range with some of North America's highest peaks. The final descent crosses the Alaska Range foothills before dropping into the Matanuska-Susitna Valley and Cook Inlet basin approaching Anchorage.