Scenic Plane Chicago Private Tour - 1 Hour

Private Chicago Plane Tour

There’s no better way to truly see the Windy City than from above on a private Chicago aerial tour that will leave you breathless—in the best way. This one-hour scenic experience takes you soaring over the North Shore and along the shimmering blue edge of Lake Michigan, where the Chicago skyline stretches before you like a postcard come to life.

Inclusions:

• This experience lasts approximately 1 hour (including take-off and landing)
• Comfortable seating with large windows
• Private flight for up to 2 passengers
• Professional, FAA-certified commercial pilot
• Views of the Chicago skyline, Lake Michigan, and iconic landmarks
• Pre-flight briefing and photo opportunities

Departing from Chicago Executive Airport in Wheeling, you’ll glide over charming neighborhoods like Glenview, Winnetka, and Evanston before tracing the shoreline toward the heart of the city. From your window seat in the sky, iconic landmarks come into view—Navy Pier, Wrigley Field, the John Hancock Center, and the mighty Willis Tower standing proudly above it all.

It’s not a lesson, not a training flight—just a pure sightseeing escape where the only job is to sit back, relax, and soak it all in. Each season reveals a different side of the city: fiery autumn foliage, snow-dusted rooftops, spring’s fresh greens, or summer’s glowing sunsets over Lake Michigan.

Perfect for couples, friends, families, or even solo adventurers, this private Chicago aerial tour offers the kind of unforgettable perspective you can’t get from the ground. Whether you’re celebrating a birthday, anniversary, or simply craving a new view of the Windy City, this is a flight you’ll be talking about long after landing.

Book your Private Chicago Plane Tour today!