ShareFlying private from Chicago to Miami no longer has to come with the full sticker shock. With JETBAY’s exclusive empty-leg offering, enjoy a premium private jet experience—at a significantly reduced rate. These repositioning flights are one of aviation’s best-kept secrets, and they don’t last long.
A Route That Balances Business and Leisure
Departing from Chicago
Chicago is more than deep-dish pizza and Wrigley Field. It’s a financial and corporate powerhouse, home to a thriving business community and some of the busiest private aviation traffic in the country.
Whether you’re flying out of O’Hare, Midway, or Chicago Executive Airport, you’ll skip the congestion and enjoy a seamless departure experience. And if time allows, Chicago’s vibrant cultural and architectural offerings—from the Art Institute to Millennium Park—are always worth the detour.
Arriving in Miami
Touch down in Miami, where the sun meets the skyline. The city is emerging as a major finance and tech hub, particularly for businesses bridging North and Latin America.
Once the work is done, unwind with:
- Unrivaled beaches and waterfront dining
- High-end shopping in the Design District and Bal Harbour
- World-class art in Wynwood
- Everglades excursions just beyond city limits
What Is an Empty-Leg Flight?
An empty-leg flight occurs when a private jet needs to reposition without passengers. Rather than fly empty, we offer these flights to our clients at a fraction of the usual charter cost—up to 75% off standard rates.
It’s the same aircraft, crew, and VIP service—just without the full price tag.
What You Should Know
- One-way only: These flights are linked to other bookings.
- Pre-set schedules: Flexibility helps, as timing is fixed.
- Subject to change: If the primary itinerary shifts, we’ll find the best alternative.
For flexible flyers, empty legs deliver incredible value without compromising the private jet experience.
Jet Recommendations: Chicago to Miami (~2h 30m flight time)
Light Jets
Embraer Phenom 300E
- Seats 6–8 passengers comfortably
- 2,010 nautical mile range
- Cruises at Mach 0.80
- Renowned for comfort, performance, and a cabin design inspired by Brazilian elegance
Cessna Citation CJ4
- Seats up to 9 passengers (ideal for 6–7)
- 410–420 ktas cruise speed
- High cruising altitude for smoother travel
- Popular for business teams needing a mix of efficiency and style
Midsize Jets
Pilatus PC-24
- Seats up to 8 passengers
- 2,300+ nautical mile range
- Can access smaller airports for added convenience
- Spacious Swiss-engineered cabin designed for both work and relaxation
Learjet 75
- Accommodates up to 8 passengers
- Sleek design and efficient for business travel
- Synonymous with executive flying—agile, fast, and productivity-focused
Why Book This Empty-Leg Flight?
Executive Efficiency
- Avoid commercial terminal stress
- Depart from private FBOs in Chicago and land in Miami with direct access to the city
- Arrive just 15 minutes before departure—no lines, no delays
Privacy and Control
- Hold meetings or relax in complete privacy
- Your preferences remembered, your schedule prioritized
- A premium experience from curb to cabin
Significant Savings
- Up to 75% off standard charter pricing
- Ideal for small teams or frequent flyers seeking elevated travel at lower cost
- Combine productivity with luxury—without overpaying
Ready to Fly?
Empty-legs like these are limited-time offers. If the Chicago-Miami route fits your plans, contact us today for a personalized consultation or to get a tailored quote.
To discover seamless, flexible travel with JETBAY, click here to get started.
Note: Empty leg availability changes based on our primary charter bookings. Images shown represent the aircraft type and might not be the exact aircraft available.