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Private Scenic Flight Over Chicago for Two

Wheeling, Illinois

NEW

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Private Scenic Flight Over Chicago for Two

Wheeling, Illinois

NEW

Number of People: 2

Duration: 1 hour

Overview

Take to the skies with a private scenic flight over Chicago, Illinois, and experience breathtaking aerial views of the city’s world-famous skyline, Lake Michigan, and iconic landmarks like Navy Pier and Wrigley Field. This one-hour sightseeing tour offers an unforgettable way to see the Windy City from above, perfect for making any occasion truly special.

✨ Fly over Chicago’s stunning North Shore suburbs, spotting landmarks like Glenview, Winnetka, and Evanston

🏙️ Soar alongside skyscrapers including Willis Tower and John Hancock Center

📸 Capture incredible photo opportunities of Navy Pier, Wrigley Field, and the bustling lakefront from the best seat in the sky

🌅 Enjoy a relaxing, one-hour journey that reveals both the natural beauty and architectural wonders of Chicago from above

Read More

Departing from Chicago Executive Airport, this aerial tour soars over the North Shore suburbs before gliding along the Lake Michigan coastline for jaw-dropping views of Chicago’s skyline. From the Sears Tower (Willis Tower) to Navy Pier and Wrigley Field, every moment in the air highlights the city’s most iconic landmarks, framed by the beauty of the lake and ever-changing seasonal scenery.

The experience lasts about an hour, making it a perfect mix of relaxation and exhilaration. With no cockpit controls or instruction to distract from the view, the focus is entirely on sightseeing and soaking up the magic of Chicago from above. Whether for a celebration or simply to see the city in a way few ever do, this private flight blends comfort, excitement, and unforgettable views into one seamless adventure.

Departing from Chicago Executive Airport, this aerial tour soars over the North Shore suburbs before gliding along the Lake Michigan coastline for jaw-dropping views of Chicago’s skyline. From the Sears Tower (Willis Tower) to Navy Pier and Wrigley Field, every moment in the air highlights the city’s most iconic landmarks, framed by the beauty of the lake and ever-changing seasonal scenery.

The experience lasts about an hour, making it a perfect mix of relaxation and exhilaration. With no cockpit controls or instruction to distract from the view, the focus is entirely on sightseeing and soaking up the magic of Chicago from above. Whether for a celebration or simply to see the city in a way few ever do, this private flight blends comfort, excitement, and unforgettable views into one seamless adventure.

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Year-Round,
Daily 7:00am - 10:00pm

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Year-Round,
Daily 7:00am - 10:00pm

Any restrictions to participate?

• Age: Children may fly if they are large enough to use a standard aircraft seatbelt without a car seat or booster. Infants or children requiring car seats cannot be accommodated.
• Health limitations: Not suitable for individuals with conditions aggravated by small-aircraft flight or motion sickness.
• Physical limitations: Participants must be able to safely enter and exit a small aircraft.

Who can you accommodate for?

• Children: Allowed if large enough for a standard seatbelt (no car seats or boosters).
• Individuals with disabilities: Accessibility is limited; small aircraft may not be suitable for those with mobility challenges.
• Languages: Flights conducted in English.
• Pets: Not permitted.

What to expect on the day of the experience?

• Duration: Approximately 1 hour of flight time, plus check-in, preflight briefing, and photo opportunities.
• What’s included:
  • Private scenic flight over Chicago for two passengers
  • Aerial views of landmarks such as Downtown Chicago, Navy Pier, Wrigley Field, North Shore suburbs, Lake Michigan shoreline, Willis Tower, and John Hancock Center
  • Preflight safety briefing
  • Opportunity for photos before and after the flight
• Who will be present: Certified FAA commercial pilot (also authorized flight instructor).
• Spectators: Guests not flying may wait at the airport.
• Photo/ video: Personal phones and cameras are welcome for photos and video. Devices must be secured during takeoff and landing.
• Specific rules to follow:
  • All safety instructions from the pilot must be followed.
  • Seatbelts must remain fastened while in flight.
  • No alcohol or disruptive behavior permitted.

How to prepare?

• Weather dependency: Flights are weather dependent. Cancellations may occur due to unsafe flying conditions. If canceled, flights can be rescheduled or refunded.
• Arrival: Arrive at least 15 minutes before scheduled departure time. Late arrivals may result in shortened flight time.
• Parking: Available at Chicago Executive Airport (PWK). Details provided with booking confirmation.
• What to wear: Dress comfortably for the season. The aircraft is heated in winter and ventilated in summer. Layers are recommended.
• What to bring: Camera, phone, and personal essentials.
• Restrooms/ lockers/ changing rooms: Restrooms are available at the airport prior to departure; no restrooms onboard.

Anything else I should know before going on this experience?

• All flights are private—just you, your guest, and the pilot.
• The experience is FAA-authorized under 14 CFR §91.147 and adheres to all safety standards, including preflight briefings and pilot drug/alcohol testing.
• Gratuities for pilots are appreciated but never expected.

Any restrictions to participate?

• Age: Children may fly if they are large enough to use a standard aircraft seatbelt without a car seat or booster. Infants or children requiring car seats cannot be accommodated.
• Health limitations: Not suitable for individuals with conditions aggravated by small-aircraft flight or motion sickness.
• Physical limitations: Participants must be able to safely enter and exit a small aircraft.

Who can you accommodate for?

• Children: Allowed if large enough for a standard seatbelt (no car seats or boosters).
• Individuals with disabilities: Accessibility is limited; small aircraft may not be suitable for those with mobility challenges.
• Languages: Flights conducted in English.
• Pets: Not permitted.

What to expect on the day of the experience?

• Duration: Approximately 1 hour of flight time, plus check-in, preflight briefing, and photo opportunities.
• What’s included:
  • Private scenic flight over Chicago for two passengers
  • Aerial views of landmarks such as Downtown Chicago, Navy Pier, Wrigley Field, North Shore suburbs, Lake Michigan shoreline, Willis Tower, and John Hancock Center
  • Preflight safety briefing
  • Opportunity for photos before and after the flight
• Who will be present: Certified FAA commercial pilot (also authorized flight instructor).
• Spectators: Guests not flying may wait at the airport.
• Photo/ video: Personal phones and cameras are welcome for photos and video. Devices must be secured during takeoff and landing.
• Specific rules to follow:
  • All safety instructions from the pilot must be followed.
  • Seatbelts must remain fastened while in flight.
  • No alcohol or disruptive behavior permitted.

How to prepare?

• Weather dependency: Flights are weather dependent. Cancellations may occur due to unsafe flying conditions. If canceled, flights can be rescheduled or refunded.
• Arrival: Arrive at least 15 minutes before scheduled departure time. Late arrivals may result in shortened flight time.
• Parking: Available at Chicago Executive Airport (PWK). Details provided with booking confirmation.
• What to wear: Dress comfortably for the season. The aircraft is heated in winter and ventilated in summer. Layers are recommended.
• What to bring: Camera, phone, and personal essentials.
• Restrooms/ lockers/ changing rooms: Restrooms are available at the airport prior to departure; no restrooms onboard.

Anything else I should know before going on this experience?

• All flights are private—just you, your guest, and the pilot.
• The experience is FAA-authorized under 14 CFR §91.147 and adheres to all safety standards, including preflight briefings and pilot drug/alcohol testing.
• Gratuities for pilots are appreciated but never expected.

Unused Experience Vouchers can be returned within 14 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 48 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 48 hours in advance means losing the value of your experience.

Unused Experience Vouchers can be returned within 14 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 48 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 48 hours in advance means losing the value of your experience.

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