Nowhere is that more on display than when touring Chicago by air.
New York City may have a more interesting skyline. Washington, D.C., may have more classic architecture, and Los Angeles may have a wider footprint. But each of these places has restrictions, whether as a result of security or overcrowding. But seeing Chicago from the air isn’t a chore. In fact, flying at a few thousand feet along Lake Michigan is the most efficient way to traverse the city.
Take a quick look at the back side of the Chicago Terminal Area Chart and the process becomes clear. Be at 2,500 feet or below by the power plant to the south or VFR waypoint VPFTS to the north, and you’re clear to go. You can talk to Chicago approach if you like, but it’s not necessary.
Along the way you’ll see Navy Pier, Willis Tower (née Sears Tower), and a park that would make a great airport. If you’re en route to Oshkosh, Wisconsin, for EAA AirVenture, a scenic Chicago skyline tour could be the cherry on top of your ultimate cross-country sundae.
As with any aerial tour, traffic can be heavy. Your aircraft should have a functioning Mode C transponder, and ADS-B In traffic advisories would be a bonus. Don’t worry about the airliners flying overhead to Chicago O’Hare and Midway. It’s your fellow general aviation pilots at the same altitude you want to make sure to avoid.