Sit on the Left side of the plane for the best views on flights from Chicago to Baltimore. While takeoff favors the right for Chicago views, the landing approach over Baltimore's Inner Harbor and Fort McHenry from the left side is more visually distinctive and geographically significant. The left side captures the most iconic features of the destination.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats capture the Chicago skyline and Lake Michigan during the initial climb. Midway typically departs runways 31L/31R or 13L/13R depending on wind; either direction favors the right side for viewing the downtown core and the lake's western shore as you gain altitude. Notable sights include: Chicago downtown skyline (Willis Tower, Trump Tower visible in the cluster), Lake Michigan's western shoreline, Bridgeport neighborhood industrial areas, Des Plaines River valley to the west.

When landing at Baltimore Washington International (BWI), sit on the Left side for the best views. Left-side seats offer views of the Patapsco River, Baltimore's Inner Harbor, and the city's historic core during descent. BWI approaches typically use runways 10L/10R or 28L/28R; the left side captures the harbor, Fort McHenry, and downtown Baltimore as you descend into the final approach corridor. Notable sights include: Patapsco River and Baltimore Inner Harbor, Fort McHenry (distinctive star-shaped fort visible from altitude), downtown Baltimore skyline, Chesapeake Bay to the east.

The flight from Chicago Midway International (MDW) to Baltimore Washington International (BWI) takes Approximately 2 hours 45 minutes to 3 hours 15 minutes.

The flight path crosses central Indiana (relatively featureless farmland and small towns), then enters Ohio where the Appalachian foothills begin to rise gently on the eastern horizon. As you approach Pennsylvania, the terrain becomes more rolling. The Appalachian plateau dominates the left (north) side of the flight path throughout Pennsylvania and into Maryland. The Susquehanna River is visible from altitude as a wide, meandering waterway in south-central Pennsylvania, roughly 90 minutes into the flight. As you descend into Maryland, the Chesapeake Bay becomes visible on the right (east) side, with its characteristic long north-south orientation and numerous tributary inlets.