Sit on the Left side of the plane for the best views on flights from Chicago to New York. The landing view of Manhattan and the Hudson River is more visually distinctive than the takeoff view. While the Chicago skyline is notable, the approach into New York offers more dramatic urban geography and water features.

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 4L/4R; eastbound departures on 31L/31R provide the best Lake Michigan views as you climb over the water. Notable sights include: Chicago downtown skyline (Willis Tower, Trump Tower visible in the cluster), Lake Michigan shoreline, Bridgeport neighborhood industrial areas, Des Plaines River valley.

When landing at La Guardia (LGA), sit on the Left side for the best views. Left-side seats offer views of the Hudson River, Manhattan's western edge, and the approach path over Queens. LGA typically lands on runways 4L/4R or 22L/22R; eastbound approaches on 4L/4R bring you over Queens and the East River, with Manhattan visible to the left. Notable sights include: Hudson River and New Jersey waterfront, Manhattan's west side skyline, East River, Queens neighborhoods and Flushing Bay.

The flight from Chicago Midway International (MDW) to La Guardia (LGA) takes Approximately 2 hours 45 minutes to 3 hours 15 minutes.

The flight path crosses Pennsylvania, passing south of the Appalachian Mountains (visible as a ridge line with valleys running northeast-southwest around 40,000 feet altitude). The Delaware River and Susquehanna River valleys are visible during cruise. As you approach New York, the Hudson River valley becomes prominent, with the Catskill Mountains visible to the northwest on clear days. The New Jersey Palisades line the Hudson's west bank during descent.