Private Jet Charter in Chicago, Priced Honestly
Private jet charter Chicago should be a simple transaction: you say where you are going and when, and somebody who knows the market comes back with real aircraft, real operators and a number that does not move after you sign. That is what this company does. We are a charter broker, we work across the whole FAA Part 135 market rather than one owner's fleet, and every quote we send names the operator, the safety rating and the tail number you will actually board.
Most of the traffic out of this city is not glamorous. It is a 6:40am departure from Chicago Executive to Teterboro with four people and a pitch deck, or a Friday run to Naples with the dogs and eleven bags. The pages on this site are built for that reader: what it costs, which airport saves you forty minutes on the ground, and when the honest answer is that you should fly commercial or drive.
What a private jet charter from Chicago actually costs
Charter is priced by the flight hour, but you do not buy flight hours — you buy a trip. The hourly rate is the spine of the quote, and then positioning, taxes, ramp fees, catering, crew overnights and, from November to March, deicing get bolted onto it. A light jet quoted at $3,800 an hour does not produce a $7,600 round trip to New York, and any broker implying otherwise is quoting you the part of the invoice they want you to see.
The table below is the honest starting point: typical Chicago market ranges per flight hour by aircraft class. Real quotes land inside these bands most of the time and outside them when the calendar is against you — the Friday before Thanksgiving, the week of CES, the Saturday of a Notre Dame home game.
For the full breakdown, including three itemised sample quotes that add up line by line, read the private jet charter cost guide. If you only want the numbers, the hourly rates by aircraft class page is the reference table.
| Aircraft class | Passengers | Range | Typical hourly rate |
|---|---|---|---|
| Turboprops | 6–9 passengers | 1,000–1,800 nm | $1,900–$3,400 |
| Very light jets | 4–5 passengers | 1,100–1,400 nm | $2,600–$3,800 |
| Light jets | 6–7 passengers | 1,300–2,000 nm | $3,200–$4,800 |
| Super light jets | 7–8 passengers | 1,900–2,300 nm | $4,200–$5,600 |
| Midsize jets | 7–9 passengers | 2,000–2,600 nm | $5,200–$7,200 |
| Super midsize jets | 8–10 passengers | 3,000–3,700 nm | $7,200–$9,800 |
| Heavy jets | 10–16 passengers | 3,600–4,500 nm | $9,500–$14,500 |
| Long range jets | 12–19 passengers | 5,000–7,700 nm | $13,500–$22,000 |
Eight Chicago airports, and why the one you pick matters more than the aircraft
Chicago is unusual: it has eight fields that a charter flight can sensibly use, and the difference between the right one and the wrong one is routinely forty minutes of driving and a four-figure swing in ramp fees. Nobody outside the industry knows this, and most brokers do not bother to explain it.
Chicago Executive (PWK) in Wheeling is the default for the North Shore and, traffic permitting, the Loop. Its 5,001 ft runway is the one real constraint — a heavy jet leaving for London at full fuel needs more asphalt, which is why DuPage (DPA) and its 7,571 ft runway exists in every serious flight plan. Midway (MDW) is closest to downtown and has full-time customs. Gary (GYY) has no curfew, which matters more than people expect when a deal runs late.
O'Hare (ORD) is available and is usually the wrong answer: you pay the highest ramp fees in the region to be sequenced behind airline traffic. There are four situations where it is genuinely correct, and the O'Hare page lists them rather than pretending. The full comparison of all eight fields is on the Chicago private jet airports hub.
The routes Chicago actually flies
Roughly two thirds of the charter demand leaving this city runs down a handful of corridors. Chicago to New York is the busiest by a distance — a 1h 55m leg on a light jet, and the most reliable source of empty legs in the country. Chicago to Miami and Chicago to West Palm Beach carry the winter migration. Chicago to Aspen is the most technically demanding leg we book, because not every aircraft type or crew is approved for the approach into ASE.
Then there is the short-haul business that competitors ignore entirely: Chicago to Nashville at 1h 10m, Chicago to Toronto with the customs paperwork that trips people up, and the sub-hour hops to Detroit, Milwaukee and Madison where the flight is shorter than the drive to the airport and a turboprop is often the smarter buy than a jet.
Every route page carries flight times by aircraft class, typical one-way price bands and a recommendation on where to land. Start at the private jet routes from Chicago hub, or browse the Midwest destinations we cover city by city.
How we choose an operator, and why it is the only thing that matters
A charter broker does not fly you anywhere. An FAA Part 135 air carrier does, and that carrier holds operational control of your flight — it decides whether the weather is acceptable, whether the crew is legal and whether the aircraft is airworthy. Choosing which certificate holder gets your trip is therefore the entire job.
Before a quote leaves this desk we confirm the operator's Part 135 certificate is current and that the specific tail is on it, check the crew's experience and currency for the aircraft and the destination, review the operator's third-party audit status with Wyvern or ARGUS where it exists, and verify insurance limits appropriate to the trip. If an operator will not produce those documents, they do not get quoted, whatever the price. The detail is on the safety and operator vetting page.
This is also why we are transparent about being a broker rather than a carrier. The broker-versus-carrier disclosure sits in the footer of every page on this site because the distinction has legal meaning, and because a company that blurs it is telling you something about how it operates.
Charter programmes beyond the standard trip
Not every flight is four executives and a briefcase. Group and team charter covers sports teams, touring parties and investor roadshows, up to a VIP airliner with 119 seats. Medical and air ambulance charter coordinates bed-to-bed transfers with specialist operators and medical crews. Air cargo charter moves AOG parts for the Midwest manufacturing base overnight.
There is also pet-friendly charter — the single most common reason first-time buyers call us — plus empty leg flights for people whose dates genuinely flex, and jet cards and memberships for those who fly enough that guaranteed availability is worth paying for. We will tell you when a card is not worth it, which is more often than the industry admits.
- Answered around the clock. A charter advisor picks up at 3am, because that is when aircraft go unserviceable.
- Part 135 operators only. Certificate, insurance and crew currency checked per trip, not once a year.
- No membership, no deposit. You pay for the flight you take.
- All-in quotes. Fuel, taxes, ramp, catering and deicing are in the number before you sign, not after.
Which aircraft class is right for your trip
The most expensive mistake in charter is buying too much aircraft. A Challenger 350 is a magnificent way to fly to Detroit and an act of financial self-harm — the trip takes 45 minutes and you will pay super-midsize money for a cabin nobody has time to enjoy. Conversely, putting eight adults and their luggage on a light jet to Los Angeles produces a fuel stop in Denver and a mutiny.
The aircraft guide works through all eleven classes with real specification tables, from a piston twin for a 300-mile hop to a VIP airliner for a touring party. The two classes that carry most Chicago traffic are light jets for anything under three hours and midsize jets for the coasts.
If you would rather not learn all this, that is legitimate. Tell us the passenger count, the bags and the date on the quote request form, and we will size the aircraft and explain why.
There is more of this reasoning written out in long form on the charter blog, and the short answers to the questions we get asked most are collected on the charter FAQ.
Frequently asked questions
How much does it cost to charter a private jet from Chicago?
A one-way light jet to New York typically runs $10,500–$14,000 all-in, and a midsize jet to Miami $21,000–$27,000. Hourly rates start around $1,900 for a turboprop and pass $16,000 for an ultra-long-range jet. The variables that move a quote most are positioning, day of week and season. The full cost guide itemises every line.
How far in advance should I book a charter out of Chicago?
For an ordinary weekday business trip, 48 to 72 hours gets you a competitive market. Same-day is routinely possible and costs more. For Aspen at Christmas, Super Bowl weekend, CES or a Notre Dame home Saturday, book four to eight weeks out — those windows genuinely sell out, and late buyers pay a premium for whatever is left.
Which Chicago airport is best for a private flight?
Chicago Executive (PWK) for the North Shore and most of the city, Midway (MDW) for downtown and full-time customs, DuPage (DPA) for the western suburbs and any heavy jet departing at full fuel, and Gary (GYY) when you need no curfew or lower fees. O'Hare is rarely the right answer. The airports hub compares all eight.
Are you a charter operator or a broker?
We are a broker. Lets Go Private Jet is a charter broker, not a direct air carrier. We do not own or operate aircraft. All flights we arrange are operated by properly licensed FAA Part 135 or Part 121 air carriers that hold operational control of the flight. That means we shop the whole Part 135 market for your trip rather than selling you the aircraft we happen to own, and it means the operator — not us — holds operational control of the flight.
Can I bring my dog on a private jet?
Usually yes, in the cabin with you, which is the main reason people move to charter in the first place. Policies vary by aircraft owner and operator, some owners decline animals outright, and cleaning fees are common. Tell us at quote stage so we filter the fleet properly. See pet-friendly charter.
What is an empty leg and can I actually get one?
An empty leg is a repositioning flight with no passengers, sold at a discount. They are real, they are cheap, and they are fragile — if the original charter moves, your flight disappears. They work only if you are flexible on date, time and airport. See empty leg flights from Chicago.
Related pages
Further reading from the blog
Sources and further reading
- FAA Part 135 operating requirements — The federal rule that governs on-demand charter and every operator we book
- NBAA — National Business Aviation Association — Industry body for business aviation standards and operating practice
- Chicago Department of Aviation — Official authority for O'Hare and Midway operations and facilities
Tell us where you are going
Send the route, the date and the passenger count. You get real aircraft options with all-in pricing, the operator's certificate and safety rating, and the tail number — usually within the hour, any hour.