Sit on the Right side of the plane for the best views on flights from Chicago to Anchorage. While the left side offers Lake Michigan views during departure, the right side captures the dramatic Chugach Mountains during the final descent into Anchorage, which is the more visually distinctive and memorable portion of the flight. The mountains provide a striking visual payoff for a long cross-country journey.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. Left side offers views of Lake Michigan immediately after departure, with the Chicago skyline visible to the south. The aircraft climbs northwestward, so the left wing captures the lake's eastern shoreline and the contrast between urban development and open water. Notable sights include: Lake Michigan, Chicago downtown skyline, Des Plaines River valley, suburban grid extending west.

When landing at Elmendorf Afb (EDF), sit on the Right side for the best views. Right side provides views of the Chugach Mountains as the aircraft descends into Anchorage from the south. The mountains dominate the approach, and the right wing captures their snow-covered peaks and the transition from Cook Inlet to the Anchorage basin. Notable sights include: Chugach Mountains, Cook Inlet, Turnagain Arm, Anchorage coastal plain.

The flight from Chicago Ohare International (ORD) to Elmendorf Afb (EDF) takes Approximately 4 hours 45 minutes to 5 hours 15 minutes.

The flight path crosses the Upper Midwest, passing over Wisconsin (visible forests and lakes), Minnesota (Mississippi River valley), and into the Great Plains of Montana and North Dakota. The Rocky Mountains appear along the western horizon during mid-flight, particularly the northern ranges in Montana. As the aircraft continues northwest into Canadian airspace, the terrain transitions to boreal forest and tundra. The flight crosses British Columbia's interior mountain ranges before descending into Alaska's coastal region, where glaciers and the Alaska Range become visible in the distance.