Many Midwestern families spend the winter around Naples, so demand rises sharply from January to March.
For a group of four to six, a light jet is the usual pick. Count on 2 hr 50 min from Midway to Naples and a quote somewhere between $15,500 and $20,500, depending mostly on the date.
Chicago to Naples private jet prices
The bill is for the aircraft, not the seats. A full cabin costs the same as an empty one, which is why groups get the best value.
| Jet size | Typical aircraft | Seats | One way | Per person, 6 flying |
|---|---|---|---|---|
| Light jetUsual pick | Phenom 300, Citation CJ3 | 6–7 | $15,500–$20,500 | from about $2,600 |
| Midsize jet | Citation XLS+, Learjet 60 | 7–8 | $17,000–$22,500 | from about $2,800 |
| Super-midsize jet | Challenger 350, Gulfstream G280 | 8–9 | $20,000–$26,000 | from about $3,300 |
| Heavy jet | Gulfstream G450, Falcon 2000 | 10–14 | $25,000–$33,500 | from about $4,200 |
These are 2026 estimates with the usual taxes and fees. Your quote will depend on the date and on where the aircraft is parked.
Check the real price for your date
What moves the price
The calendar moves prices the most. The season runs roughly January to April.
Naples Municipal sits close to downtown and Port Royal.
Booking the return on the same aircraft is usually cheaper than two separate one-way trips.
Fees to ask about
Quotes don't always show everything up front. Here's what can be added:
- Landing, parking and handling fees at Midway and Naples.
- De-icing in winter at Midway. Worth asking about if you fly between December and March.
- Crew overnight costs if you keep the same aircraft for the return.
A good broker will give you the all-in figure without being asked twice. Every fee is explained in our guide to charter fees.
Flight time from Midway to Naples
Typical airborne time from Midway to Naples, by aircraft size:
| Jet size | Time in the air | Nonstop? |
|---|---|---|
| Light jet | about 2 hr 50 min | Yes |
| Midsize jet | about 2 hr 40 min | Yes |
| Super-midsize jet | about 2 hr 35 min | Yes |
| Heavy jet | about 2 hr 30 min | Yes |
1,132 miles (984 nautical miles) between Midway and Naples, in a straight line.
Which airports to use
Leaving Chicago
Departures mostly use Midway (MDW), about 9 miles from the Loop. Other options: Chicago Executive (PWK).
Arriving in Naples
- Naples (APF), about 1 miles from downtown Naples in a straight line. Close to downtown Naples and one of the busiest private jet airports in Florida in winter.
Best jet size for Chicago to Naples
A light jet covers this nonstop with normal luggage. Step up to a midsize if you want to stand up inside or you're bringing bulky bags.
Good to know on this route
- Return trips cluster around Easter and the end of the season in April.
- Chicago Executive is a convenient departure for families living on the North Shore.
- Christmas and New Year's weeks fill up early.
How to pay less
- Be open on airports: a nearby airport sometimes has a cheaper aircraft available.
- Book the return together: a round trip on the same aircraft is often cheaper than two one-way flights.
- Look for empty legs: repositioning flights sold at a discount. The timing is fixed and they can disappear at short notice.
- Move by a day: the day before or after a peak date can make a real difference.
Booking takes a few steps: send your dates and passenger count, compare all-in quotes, check the operator and sign. Our booking guide walks through each one.
Get a quote for Chicago to Naples
Takes a minute. A charter partner can send you real options for your date.
Questions
How much is a private jet from Chicago to Naples?
About $15,500 to $20,500 one way in a light jet. Midsize jet: $17,000 to $22,500. Super-midsize jet: $20,000 to $26,000. Heavy jet: $25,000 to $33,500. Dates, positioning and fees decide where you land in the range.
How long is the flight from Chicago to Naples?
About 2 hr 50 min in a light jet, airport to airport, for 1,132 miles.
Which airports do private jets use for Chicago to Naples?
Most flights leave Midway (MDW) and land at Naples (APF). Alternatives include Chicago Executive (PWK).
Can I find an empty leg on this route?
Occasionally. Ask the broker to alert you: discounted repositioning flights on this route come and go quickly.
How do I know the operator is safe?
The operator should hold an FAA Part 135 certificate. Many also carry ARGUS or Wyvern ratings, which are worth asking for.
Other routes
How we estimate prices
None of these figures is a quote. They come from the straight-line distance, a typical speed for each jet size and an all-in hourly range calibrated on prices charter companies publish. Full method on the cost calculator page.