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Chicago, Illinois → Naples, Florida

Private Jet Charter from Chicago to Naples

If you’re leaving the North Shore for a week in Naples, your best departure may be in Wheeling. If everyone is coming from downtown, start with Midway. On the Florida side, a dinner reservation on Fifth Avenue South calls for a different plan than a late arrival at a home in Bonita Springs. Here’s how we’d put each trip together.

Aircraft & flight time

Featured airport pair: Chicago Midway (MDW) to Naples (APF)

The estimates start with this pair. Select another listed airport to compare.

CategoryEst. nonstop timeEstimated max passengers
Light jet2h 45m – 3h 20mUp to 9
Midsize jet2h 35m – 3h 10mUp to 8
Super-midsize jet2h 25m – 3h 00mUp to 10

Planning estimates use straight-line distance, assumed category speeds and an allowance for climb, descent and routing. Actual time and nonstop capability depend on the aircraft, winds, passenger and baggage load, and airport conditions. Fuel stops and ground time are excluded. Passenger counts are upper-end seating examples for each category. The number your flight can carry depends on the aircraft layout, baggage, fuel and airport conditions.

Planning detail 01

Choose the Chicago airport by where your guests are starting

From the Loop or South Loop, start with Midway. From Lake Forest, Highland Park or nearby North Shore communities, compare Chicago Executive in Wheeling. From St. Charles, Geneva or the western suburbs, look at DuPage in West Chicago. If one guest is flying into O’Hare to join you, compare departing from O’Hare before building in a cross-town drive. Even at the same airport, allow time to collect checked bags and get from airline arrivals to the private terminal.

Planning detail 02

Land closer to your plans on the Gulf Coast

Naples Airport is the first arrival to compare for Old Naples, Fifth Avenue South, Port Royal or Marco Island. For a home in Estero or northern Bonita Springs, compare Southwest Florida International in Fort Myers using your exact address. If you need a late arrival or an early departure, Naples Airport asks aircraft to observe voluntary quiet hours from 10 p.m. to 7 a.m. local time. We’ll compare Fort Myers if your preferred timing falls in that window and arrange a car from the private terminal to your door.

Planning detail 03

Work backward from dinner, a tee time or a family gathering

Naples is one hour ahead of Chicago. If your flight leaves at 2 p.m. Chicago time and takes three hours, you land at 6 p.m. Naples time, before you’ve unloaded and met your driver. For a 7 p.m. dinner in Old Naples, we’d build the schedule around when you want to be at the restaurant. If you’re heading straight to the course, we’ll allow time to check in and have the car sized for the clubs as well as the guests.

Questions about Chicago to Naples charters

Could deicing cost extra on a winter departure from Chicago?

Yes. If the aircraft needs deicing, it’s billed separately after your flight. When hangar space is available, we’ll try to arrange it before departure to reduce the chance of needing deicing. The aircraft may still need to be deiced if conditions call for it.

Can six guests bring six sets of clubs and suitcases?

Yes, with the right aircraft and ground transportation. Six available seats don’t tell us what fits through the baggage door or how much room is in the hold. Give us the number of golf bags and suitcases up front so we can compare cabins.

Can we fly into Naples and return from Fort Myers?

Yes. If you’re spending the first part of your trip in Old Naples and finishing in Estero, we can quote different airports for each leg. We’ll confirm both private terminal addresses and coordinate the pickup for each end of your stay.