Sit on the Right side of the plane for the best views on flights from Chicago to Juneau. While takeoff offers Chicago's urban landscape, the right side dominates the longer flight segment. The route crosses the northern Great Plains and Canadian interior before reaching the Alaska panhandle's dramatic coastal mountains, glaciers, and Inside Passage waterways—all best viewed from the right side during the approach and descent into Juneau.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD typically departs westbound or northwestbound. Left-side seats face toward Lake Michigan and the Chicago shoreline during initial climb, offering views of the lakefront, downtown skyline, and the transition from urban sprawl to open water. Notable sights include: Lake Michigan (immediate eastern boundary), Chicago downtown skyline and Willis Tower, suburban grid extending westward, Des Plaines River valley.

When landing at Juneau International (JNU), sit on the Right side for the best views. Approaching JNU from the southeast, right-side seats offer views of the Inside Passage waterways, Gastineau Channel, and the dramatic coastal mountains surrounding Juneau. The approach typically descends over water with Admiralty Island and the Chilkat Range visible on the right. Notable sights include: Gastineau Channel (narrow water passage), Admiralty Island (forested landmass), Chilkat Range (snow-capped peaks), Mendenhall Glacier (visible as white expanse in valley).

The flight from Chicago Ohare International (ORD) to Juneau International (JNU) takes Approximately 5.5 to 6 hours.

The flight path crosses the Upper Midwest (Minnesota, Wisconsin), enters Canadian airspace over Ontario, passes over the boreal forests and lakes of northern British Columbia and Yukon Territory, then descends into Southeast Alaska's coastal mountain ranges. Notable geographic features include the Canadian Shield's lake-dotted terrain, the Rocky Mountain foothills (distant views), and the transition from interior forest to the temperate rainforest and glacier-carved valleys of the Alaska panhandle. The Inside Passage waterways—including Clarence Strait and Stephens Passage—become visible during the final descent approach.