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Dupage to Chicago Midway

DPAChicago/West ChicagoChicago/West Chicago
MDWChicagoChicago

Date

2nd November 2026

Passengers

10 pax

Charter Price

$8,600

Duration

33m

Aircraft

Challenger 300

Challenger 300 aircraft
Challenger 300 from the operator's fleet.
DPAMDWChicago/West ChicagoChicago33m · 27 mi

About this flight

Fly from Chicago/West Chicago to Chicago on an empty leg connecting the western suburbs with a convenient arrival closer to the city. On 02 November, the route offers a distinctive way to organise an autumn day around meetings, an evening engagement or a stay in the heart of Chicago. The journey is short, but choosing a private jet keeps the experience focused on your own schedule and the people travelling with you. Once in the city, celebrated architecture, restaurants and cultural venues provide plenty of reasons to make the most of the season.

The Bombardier Challenger 300 brings midsize jet comfort to this brief cross-city flight, offering a spacious cabin in which to settle in from departure to arrival. Its 10 seats accommodate a group travelling together, whether colleagues are continuing a working day or friends are heading into town. Comfortable seating and an environment suited to conversation help make even a short flight feel considered rather than hurried. There is also room for the belongings that accompany a business visit or autumn city break, adding to the practicality of the experience.

Because an empty leg follows an aircraft’s existing flight plans, this route presents an unusual charter opportunity for travellers who can match its timing and direction. It turns a necessary repositioning journey into a memorable way to arrive in Chicago, combining the convenience of private aviation with the appeal of a well-planned autumn itinerary.

Flight details

From
Dupage Airport (DPA)
To
Chicago Midway International Airport (MDW)
Date
2nd November 2026
Estimated flight time
33m
Aircraft
Challenger 300
Seats
Up to 10 passengers
Price
$8,600 for the whole aircraft
Empty leg enquiry

Enquire, or make an offer

Listed at $8,600 for the whole aircraft. Ask about it as listed, or tell us what you would like to pay.
Listed price
$8,600For the whole aircraft, as listed.

Passengers

1

We confirm availability with the operator and reply by email. Nothing is charged.

Listed flights on the same route or from the same airports, nearest dates first.

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1.

What is an empty leg flight?

An empty leg flight occurs when a private jet needs to return to its home base or reposition for the next charter without passengers.

2.

How flexible are empty leg flight times?

Empty leg flights have fixed departure times and destinations since they are repositioning flights. However, we have access to thousands of empty legs across the globe, so there is often flexibility in finding a flight that matches your schedule.

3.

How do I find available empty leg flights?

Our team monitors empty leg availability in real-time across our global network of operators. Simply enter your desired route and dates, and we will notify you of matching opportunities. You can also browse our current listings above.

4.

Are empty leg flights safe?

Absolutely. Empty leg flights use the same aircraft, crews, and safety standards as regular charter flights.

Testimonials

What our customers say about us

01/16

All went very well! Already planning next year's trip — might need a bigger jet for eight of us next time.

S.M.Private Client