Market · Chicago, IL

Flying private in Chicago

Start with the Loop, the North Shore or the suburb you need to reach. We compare Chicago’s airport options with the cabin and schedule that fit your trip.

Airports

The airports, and when each one wins.

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Airport locations, north up. This schematic is not a navigation map. Check road traffic and the exact FBO address before travel.
MDW · Chicago Midway International

When it wins

A Chicago option with dedicated private aviation facilities. Compare it for city plans against your final address and the ground journey.

Ground travel: Use the chosen FBO address for pickup, not the airline terminal.

Any drive times are approximate; traffic and FBO location affect the journey.

Depart from MDW View ground directions

PWK · Chicago Executive

When it wins

Consider Chicago Executive for the north and northwest suburbs. Aircraft performance and airport arrangements still need checking for your dates.

Ground travel: Compare the drive to the North Shore, your office or hotel before committing to a city center airport.

Any drive times are approximate; traffic and FBO location affect the journey.

Depart from PWK View ground directions

ORD · Chicago O’Hare International

When it wins

Worth discussing for plans near O’Hare or an airline connection. Airport traffic, private aviation arrangements and transfers are part of the comparison.

Ground travel: An airline connection needs enough time to transfer from the FBO and complete airline check in.

Any drive times are approximate; traffic and FBO location affect the journey.

Depart from ORD View ground directions

Plan the drive from the airport

Compare the airport against your hotel, home or meeting location. Directions open in Google Maps.

Confirm your FBO’s exact pickup address before travel. Traffic and arrival conditions can change.

The season

When Chicago is busy, and what it does to price.

Winter weather and busy event periods can affect the aircraft, schedule and airport choice. We discuss timing flexibility and alternatives while the trip is being planned.

Routes

Plan a route in or out.

Explore the route, compare cabin options and start a trip request.

Aircraft

What fits the runway and the mission.

Regional trips can suit a light or midsize cabin, depending on the group and bags. For a longer flight, compare room to stand, seating comfort, lavatory access and space to work before comparing price. Airport performance is checked for the actual airplane and expected conditions.

Local notes

Details to plan before you fly.

  • The North Shore and downtown can favor different airports.
  • Include extra bags or sports equipment in the request.
  • Share a backup departure time if a meeting or weather changes the day.
  1. 1 · Trip
  2. 2 · Contact
  3. 3 · Options

Enter your trip and contact details to receive a planning estimate by email. No payment is required.

Trip type
City, airport name or code

Use local time at each departure airport. We confirm timing and time zones with your itinerary.

Our standards

Every airplane has to fit the trip.

  • We review the airplane, its condition, the pilots’ experience and the requirements of your trip.
  • Our starting preference is an airframe from 2005 or newer. An exception comes with an explanation.
  • Your written quote identifies the airplane, what the price includes and the terms that could change it.
Fair questions

Flying private in Chicago questions.

Midway or Chicago Executive?

Start with your final address. Midway is a city option; Chicago Executive is worth comparing for the north and northwest suburbs. We review the aircraft and drive together.

What happens if winter weather affects the trip?

We discuss available changes in timing or airport and keep you informed. The flight crew determines whether the flight can operate in the conditions.