Flying private from Chicago to Aspen, most groups end up in a midsize jet. Expect roughly $16,500 to $22,000 one way and 2 hr 35 min in the air.
Chicago is one of the biggest sources of private traffic into Aspen in ski season. Below: real price ranges by jet size, the airports that make sense, and the dates to avoid if you're watching the budget.
What you'll pay to fly private from Chicago to Aspen
You charter the whole aircraft, so the price is the same with two passengers or a full cabin. Split between friends or colleagues, it gets a lot less scary.
| Jet size | Typical aircraft | Seats | One way | Per person, 6 flying |
|---|---|---|---|---|
| Light jet | Phenom 300, Citation CJ3 | 6–7 | $15,000–$20,000 | from about $2,500 |
| Midsize jetUsual pick | Citation XLS+, Learjet 60 | 7–8 | $16,500–$22,000 | from about $2,800 |
| Super-midsize jet | Challenger 350, Gulfstream G280 | 8–9 | $19,500–$25,000 | from about $3,200 |
| Heavy jet | Gulfstream G450, Falcon 2000 | 10–14 | $24,000–$32,500 | from about $4,000 |
2026 ranges, fees included. Treat them as a guide: the real quote moves with dates and aircraft availability.
Check the real price for your date
What moves the price
Aspen sits at 7,820 feet with mountains close by, so operators restrict which aircraft and crews can fly in.
Dates matter more than most people expect. Ski season runs roughly late November to early April, with Christmas and Presidents' Day the busiest weeks.
And a jet that has to fly empty to pick you up costs more than one already sitting at Midway.
What the price leaves out
Before comparing two quotes, check whether they include these:
- Handling, parking and landing fees charged by the terminals at Midway and Aspen.
- Winter de-icing at Midway: rarely mentioned in the first quote, sometimes significant on the invoice.
- Crew hotel and per diem if the aircraft waits for you in Aspen.
Get the total in writing before you commit. Every fee is explained in our guide to charter fees.
Time in the air
The jet size changes the flight time a little, the price a lot. Time in the air:
| Jet size | Time in the air | Nonstop? |
|---|---|---|
| Light jet | about 2 hr 45 min | Yes |
| Midsize jet | about 2 hr 35 min | Yes |
| Super-midsize jet | about 2 hr 30 min | Yes |
| Heavy jet | about 2 hr 25 min | Yes |
1,018 miles (884 nautical miles) between Midway and Aspen, 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 Aspen
- Aspen (ASE), about 4 miles from downtown Aspen in a straight line. A mountain airport at 7,820 feet, with tighter operating limits than most. Some larger jets can't use it, and winter weather can close it.
- Eagle County (EGE), about 32 miles from downtown Aspen in a straight line. Near Vail. The usual backup when Aspen is closed or the jet is too big, at the cost of a longer drive.
Best jet size for Chicago to Aspen
Go midsize if you're four or more with bags. It's the size most operators propose first on this trip.
Good to know on this route
- If weather closes Aspen, flights usually divert to Eagle County, which means a long drive over mountain roads.
- Christmas, New Year and Presidents' Day weekends are the most expensive dates to fly.
- Summer brings a second, smaller peak in July and August.
How to pay less
- Move by a day: the day before or after a peak date can make a real difference.
- Fly midweek: Tuesday to Thursday departures are usually cheaper than Fridays and Sundays.
- Book the return together: keeping the same aircraft for the return is often cheaper than booking two separate one-way trips.
- Be open on airports: a nearby airport sometimes has a cheaper aircraft available.
From request to boarding, the process is short. See how to book a private jet for the details.
Get a quote for Chicago to Aspen
No cost, no obligation. A charter partner can send you actual aircraft and an all-in price.
Questions
How much is a private jet from Chicago to Aspen?
About $16,500 to $22,000 one way in a midsize jet. Light jet: $15,000 to $20,000. Super-midsize jet: $19,500 to $25,000. Heavy jet: $24,000 to $32,500. Dates, positioning and fees decide where you land in the range.
How long is the flight from Chicago to Aspen?
About 2 hr 35 min in a midsize jet, airport to airport, for 1,018 miles.
Which airports do private jets use for Chicago to Aspen?
Most flights leave Midway (MDW) and land at Aspen (ASE). Alternatives include Chicago Executive (PWK), Eagle County (EGE).
Can I find an empty leg on this route?
Sometimes. Empty legs appear when a jet repositions after dropping off a client. They cost less, but the time is fixed and the flight can be cancelled.
How do I know the operator is safe?
Ask for the operator's FAA Part 135 certificate and whether it holds an ARGUS or Wyvern rating. A serious broker answers right away.
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.