Private Jet from Chicago, US (MDW) to Key West, US (EYW)
Charter private jets from Chicago (MDW) to Key West (EYW). Compare prices, view aircraft options and book your luxury flight instantly.
Private jet charter from Chicago to Key West
The route from Chicago (MDW) to Key West (EYW) covers approximately 1,994 km, about 3h 49m nonstop by private jet.
We did not observe a regular nonstop pattern between Chicago and Key West over the last 12 months, so this sector is normally flown ad hoc. Departure-end activity is solid though: 24,583 business aircraft movements were tracked at Chicago, around 2,049 a month.
Aircraft based at or passing through Chicago are led by the Cessna Citation Latitude and the Embraer Phenom 300, with an average build year of 2014 — that is the pool a charter for this route is most likely to come from.
At the arrival end, Key West recorded 521 tracked movements over the same period (about 43 a month), most often the Pilatus PC-12.
Departures from Chicago are weekday-led (62% of movements Monday to Thursday) — the classic sign of a business field, where weekend positioning is often available at short notice.
The smallest cabin that covers 1,994 km without a fuel stop is the very light jet at $1,500-4,500 an hour, and the type most often quoted here is the Bombardier Challenger 350. How the hourly rate turns into a total is set out in the private jet cost guide, and if the dates are loose it is worth checking empty leg flights on this direction first.
Available Flights
Browse available private jets for your charter flight from Chicago Midway International Airport to Key West International Airport. Compare aircraft options, prices, and specifications.
Dassault Falcon 6X
$32,442 - $47,708
3.8h × $8,500-$12,500/hr
Honda HondaJet Elite S
$10,305 - $15,648
3.8h × $2,700-$4,100/hr
Gulfstream G700
$36,258 - $51,525
3.8h × $9,500-$13,500/hr
Flight Summary: Chicago → Key West
1,994 km route
Traffic at Both Ends: Chicago and Key West
No regular nonstop pattern observed on this sector — here is the activity we did track over 12 months
Departure: Chicago
Thursday is the busiest day, departures cluster around 21:00–00:00 UTC.
Arrival: Key West
Friday is the busiest day, departures cluster around 18:00–21:00 UTC.
Departure: Chicago Midway International Airport
Chicago, US
Chicago Midway International Airport is a major international airport located in Chicago, US. The airport provides excellent private aviation services with dedicated facilities.
Private Jet Facilities
Ground Services
Full customs and immigration services available 24/7. 100LL and Jet A-1 fuel available 24/7.
Arrival: Key West International Airport
Key West, US
Key West International Airport is a major international airport located in Key West, US. The airport provides excellent private aviation services with dedicated facilities.
Private Jet Facilities
Ground Services
Full customs and immigration services available 24/7. 100LL and Jet A-1 fuel available 24/7.
Best Private Jets from Chicago to Key West
Our recommended aircraft for this route, optimized for distance, passenger capacity, and cost efficiency.
Challenger 350
EFFICIENTChallenger 3500
EFFICIENTChallenger 650
EFFICIENTHow Much Does It Cost to Charter from Chicago to Key West?
Real-time cost calculation based on your selected aircraft type and passenger count.
Estimated Total Cost
Mid-Size Jet • 1 passenger
Includes fees & positioning
Cost Breakdown
Money-Saving Tips
Best Value Months
Softest months across the charter market; we have too few tracked flights on this sector to judge its own seasonality.
Onboard Services for Chicago to Key West Private Jets
Standard on the aircraft classes that fly this route.
Entertainment
Catering
Comfort
Connectivity
Special Features
Highlights
Private Jet Comparison: Chicago to Key West Routes
Compare all available private jet options with detailed specifications, rental costs, and performance data.
| Aircraft | Flight Time | Passengers | Range | Price Range | Popularity | Suitability | Action |
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2h 51m | Up to 8 | 5,926 km | $13,660 - $19,352 |
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| 2h 51m | Up to 8 | 6,296 km | $14,229 - $19,921 |
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| 2h 51m | Up to 10 | 7,408 km | $15,652 - $21,344 |
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| 2h 51m | Up to 10 | 10,926 km | $18,498 - $25,613 |
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| 2h 51m | Up to 12 | 12,223 km | $20,490 - $28,459 |
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2h 51m | Up to 14 | 14,260 km | $28,459 - $39,842 |
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Available Aircraft Classes for Chicago to Key West Flights
Explore all aircraft classes suitable for this route. Compare by passenger capacity, range, and hourly rates to find the perfect jet.
Very Light Jet
Not SuitableCovers the 1,994 km with 506 km to spare. About $7,100 for this sector.
Popular models:
Citation Mustang, Phenom 100, Eclipse 550
Ideal for:
Short business trips, regional flights
Light Jet
Not SuitableCovers the 1,994 km with 2,006 km to spare. About $10,000 for this sector.
Popular models:
Citation CJ3+, Learjet 75, Phenom 300
Ideal for:
Medium-distance flights, small groups
Seen here:
17% of movements tracked at the field, led by the Embraer Phenom 300.
Midsize Jet
Limited RangeCovers the 1,994 km with 3,506 km to spare. About $12,800 for this sector.
Popular models:
Citation Latitude, Hawker 900XP, Learjet 60XR
Ideal for:
Continental flights, business groups
Seen here:
34% of movements tracked at the field, led by the Cessna Citation Latitude.
Super Midsize Jet
Perfect MatchCovers the 1,994 km with 5,506 km to spare. About $18,500 for this sector.
Popular models:
Citation X+, Challenger 350, G280
Ideal for:
Transcontinental flights, luxury travel
Seen here:
29% of movements tracked at the field, led by the Bombardier Challenger 350.
Turboprop
Not SuitableCovers the 1,994 km with 1,006 km to spare. About $5,100 for this sector.
Popular models:
King Air 350, TBM 960, Pilatus PC-12
Ideal for:
Short regional flights, cost-effective
Not shown here because they cannot make 1,994 km without a fuel stop: Large Cabin Jet, Ultra Long Range . A technical stop adds an hour and landing fees, so on this sector they only make sense if the cabin size matters more than the schedule.
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Market Trends for Chicago to Key West Charters
View seasonal pricing patterns and demand fluctuations to find the best time to book your flight.
Popular Jets on Chicago to Key West Route
See which aircraft are most frequently chosen by travelers on this route.
Charter Cost Breakdown: Chicago to Key West
Detailed breakdown of all fees including base flight cost, fuel surcharge, permits, crew, and positioning.
Weather Considerations for Chicago to Key West Flights
Monthly weather patterns and how they affect flight operations throughout the year.
Related Routes
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Frequently Asked Questions
Find answers to common questions about charter costs, booking process, aircraft options, and travel requirements.
How busy is private aviation out of Chicago?
24,583 business aircraft movements were tracked at Chicago over the last 12 months, most commonly the Cessna Citation Latitude. We did not see a regular nonstop pattern to Key West in that period, so expect an ad hoc charter rather than a well-worn sector.
What aircraft operate into Key West?
521 movements were tracked at Key West, led by the Pilatus PC-12, average build year 2009.
How long does a private jet flight from Chicago to Key West take?
Flight time varies by aircraft type, typically ranging from 1h to 2h for this 1,994km route.
What's the cost of a private jet from MDW to EYW?
Pricing depends on aircraft size and season, typically ranging from $19900 to $39900 for this route.
How far in advance should I book?
We recommend booking 24-48 hours in advance for best aircraft availability, though same-day flights are often possible.
Can I bring pets on the private jet?
Yes, pets are welcome on private jets. International flights require health certificates and may need quarantine arrangements.
What amenities are available on board?
Amenities vary by aircraft but may include Wi-Fi, entertainment systems, gourmet catering, bedroom suites, and shower facilities.
Is catering included in the charter price?
Basic refreshments are typically included, but gourmet catering can be arranged for an additional fee based on your preferences.
Flight Details: Chicago to Key West Route
Detailed technical information including flight distance, navigation details, airspace regulations, and operational requirements.
Flight Details
Regulations
Weather Conditions
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