Naples Airport is just east of downtown. Old Naples and Fifth Avenue South are about ten minutes away, Port Royal and Pelican Bay about 15, and Marco Island 35 to 45 minutes. The main runway is about 6,600 ft, which takes every category on this page. One FBO, run by the airport authority. In season the ramp fills, so parking is the first thing we confirm with the operator. The airport asks jets to stay on the ground between 10 pm and 7 am, and operators we work with plan around it, so a Chicago departure that lands in Naples before dark is the easy plan.
Private jet charter
Naples to Chicago
Naples to Chicago is the snowbird run, and half of it is booked from the Chicago end. Submit your dates and a pilot reviews the aircraft available for them, then sends a written quote, as soon as the desk can review your request.
- 1 · Trip
- 2 · Contact
- 3 · Options
Enter your trip and contact details to receive a planning estimate by email. No payment is required.
Your cabin options
Peak travel dates may affect availability and pricing. We confirm both for the proposed airplane.
Review your trip
Typical aircraft
Aircraft options for this route.
Compare these options, then tell us your plans. We will confirm the fit, availability and flight time for your aircraft.
Light jet
Phenom 300
6 to 8, up to 9 with the belted lavatory seat · ~2,000 nm
About 2 of this type through operators we work with.
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Midsize jet · we place clients on this type regularlyCitation Excel and XLS+
7 to 9 seats · ~1,700 to 1,800 nm
About 5 of this type through operators we work with.
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Super midsize jet · we place clients on this type regularlyCitation X
8 to 9 seats · ~3,100 nm
About 4 of this type through operators we work with.
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Airports
The airports on both ends, and why.
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Your dates and traveler count are retained when you choose an alternative.
Depart
Arrive
APF · Naples Airport
RSW · Southwest Florida International
Southwest Florida International in Fort Myers is about 45 minutes north of Old Naples on Interstate 75, longer in season traffic. It has a 12,000 ft runway and its own general aviation ramp. It wins for heavy jets, for large groups, and on the peak weeks when Naples has no parking left. For Bonita Springs, Estero and Sanibel it is often the closer airport anyway.
MDW · Chicago Midway International
Midway is on the southwest side of Chicago, about 10 miles from the Loop: 20 to 25 minutes with clear roads and 40 to 50 minutes in rush hour. The main runway is about 6,500 ft, which works for every category on this page. Airline traffic shares the field, but the FBOs sit on their own side of it, so you never see the terminal. It is the close airport for downtown, the Gold Coast, Lincoln Park and Hyde Park.
PWK · Chicago Executive
Chicago Executive is in Wheeling, in the north suburbs. It is 15 to 25 minutes to the North Shore towns and the Northbrook and Deerfield offices, and 40 to 50 minutes to the Loop. The main runway is about 5,000 ft, fine for light and midsize jets and for many super midsize jets on a dry day. No airline traffic, so it stays calm when Midway is backed up by weather.
From the cockpit
What a pilot would tell you about this leg.
Much of Naples winters here from the Midwest, so this is a route we quote in both directions from Thanksgiving through Easter. The tightest weeks are Christmas through New Year, Presidents Day weekend and the March spring breaks, when Chicago families head south and Florida based aircraft are spoken for early. On those dates the aircraft that flies you is often positioned in from another city, which is why a one way estimate runs wider than a round trip. Summer flips the route: Naples heads north to the lake for July and August, and availability is easier both ways.
- Chicago winters mean deicing. It adds time on the ground and shows up as a line on the quote when it happens. We tell you before the trip, not after.
- Lake effect snow and low cloud at Midway are common from December to February. When the forecast is poor the crew may wait for a window or use Chicago Executive. Both are decided the day before, with you.
- The flight north in winter is often a little longer than the flight south because of headwinds. The estimate does not add wind, so treat the flight time as a calm day.
- For a family with winter coats and two weeks of bags, a midsize or super midsize gives you a stand up cabin and the baggage space. A light jet does the trip well for four with weekend bags.
- Midway's runways are shorter than O'Hare's. That matters for some heavy jets, not for the categories on this page.
Empty legs
Exact matches and nearby opportunities.
No sample empty leg matches this exact direction. Ask us to check your dates.
Related departures and arrivals
These involve one of the airports on your route, but do not fly the same itinerary.
Check the current published flights for availability, or ask us to review your dates.
View current empty legs →See aircraft and planning estimates, or join the email list →
Fly this route more than three times a year?
The CP Jets jet card
Prepaid flight hours in one aircraft category, availability with notice, and a pilot behind every trip. Rates come in a written proposal after a short fit check.
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
Naples to Chicago questions.
How much does a private jet from Naples to Chicago cost?
Your emailed planning estimate shows the current range by category for your dates. A light jet sits at the low end, a midsize or super midsize higher. A one way runs wider than a round trip because the aircraft has to get into position. Your written quote identifies the aircraft, total price, included taxes and fees, exclusions and any charges that may change.
Which Chicago airport should I use?
Midway for downtown, the Gold Coast, Lincoln Park and the South Side. Chicago Executive for the North Shore and the northern suburbs. O'Hare is possible but rarely the right choice for this trip: farther from downtown and more airline traffic. Tell us where you are going and we pick with you.
How far ahead should I book Chicago to Naples in winter?
Two to three weeks in the peak weeks. The Christmas to New Year stretch and the March spring breaks sell out first. Outside those weeks a few days is usually enough, and same day trips happen when an aircraft is already nearby.
What happens if a snowstorm hits Chicago on my travel day?
The crew watches it from 48 hours out. The usual options are to move the departure a few hours, leave a day early, or switch to the other airport. We call you with the plan. Weather changes are worked out with the operator, and we tell you what any change means for the quote before anything moves.
Can I bring the dog?
Usually, yes. Pets ride in the cabin on many of the aircraft we source, and a few operators have rules by size. Tell us when you ask for the quote and we only show aircraft that take your dog.