Sit on the Right side of the plane for the best views on flights from Chicago to New York. The right side wins overall because the Chicago departure view is genuinely spectacular — the full skyline and lakefront together — and during the cruise the right side also tracks closer to the southern shore of Lake Erie and the Pennsylvania landscape. The Manhattan arrival on the left is excellent but brief; the Chicago departure on the right is the highlight of the flight.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. Departing east from ORD on runways 10R/10L or 9R/9L, the right side faces south and gives you a clear view of downtown Chicago's skyline, including the Willis Tower and the lakefront. The left side looks north toward the suburbs with little of interest. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Grant Park and Museum Campus, Chicago River grid.

When landing at La Guardia (LGA), sit on the Left side for the best views. LGA's most common approach is from the northeast on runway 31, meaning the aircraft swings over Long Island Sound and turns final heading southwest. The left side gets a direct view of Manhattan's skyline, the East River, and the Bronx as you descend. The right side looks out over Queens and Long Island with no comparable landmarks. Notable sights include: Manhattan skyline (Midtown and Lower Manhattan), East River, Long Island Sound, Rikers Island.

The flight from Chicago Ohare International (ORD) to La Guardia (LGA) takes Approximately 2 hours to 2 hours 20 minutes.

The flight tracks roughly east-northeast across northern Indiana, then over Toledo and the southern shore of Lake Erie in Ohio, crossing into Pennsylvania near Erie. Over Pennsylvania the terrain rises into the Allegheny Plateau with forested ridgelines visible below. The flight then crosses into New Jersey before the descent into LGA over Long Island Sound.