Empty Leg Flights in Chicago, IL

Save Big on Private Jet Rentals with an Empty Leg to/from Chicago

Find the best deals on private flights to/from Midway, O’Hare, DuPage, and other airports around the Windy City with an empty leg flight to/from Chicago, IL!

Chicago is the busiest region for private aviation in the Midwest, with executive jets and charter planes flying in & out every hour. As flights are booked in Chicago and across the country, empty leg deals become available for savvy jetsetters. Booking one of these flights allow flexible travelers to save 25%, 30%—up to 50% (or more) on the price of private jet charters!

Call us anytime or request a quote for empty legs in Chicago. Our brokers have access to all of the charter planes available in Illinois and across the United States. Whether you’re looking for empty legs to Chicago, or deadheads from the Windy City, you can get an amazing deal from Chicago Private Jets.

Currently Empty Leg Deals in Chicago, IL

Private Flight from Chicago, IL to Minneapolis, MN on November 18th, 2022

Fly on a private jet from Chicago to Minneapolis at just a quarter of the regular price! This Cessna Citation Sovereign is available to depart from Chicago Executive Airport (PWK) at 3:00 PM local time, and will arrive at Minneapolis−Saint Paul International Airport (KMSP) in Minneapolis, MN. This super midsize jet can seat up to 8 passengers and comes with Wi-Fi available on-board.

Cessna Citation Sovereign


Private Flight from Minneapolis, MN to Chicago, IL on November 23rd, 2022

Charter a private flight from Minneapolis to Chicago at a substantial discount! This Cessna Citation Sovereign will depart from Minneapolis−Saint Paul International Airport (KMSP) in Minneapolis, MN at 10:30 PM local time, and will arrive at Chicago Executive Airport (PWK) in Wheeling, IL. Up to 8 passengers can travel on this super midsize jet, and Wi-Fi is available during the flight.

Cessna Citation Sovereign


How do Empty Legs become available?

Whenever a one-way flight or multi-leg flight is booked, or a plane needs to re-position to another airport or its home base, an empty leg becomes available.

Empty legs are most often created by one-way flights. These trips are often priced as a round-trip, with the person booking responsible for the cost of the return trip.

For example: we arrange a one-way flight for a client on a light jet from New York City to Chicago-Midway, with the return leg included in the cost. After dropping off passengers in Chicago, the plane has to fly home to Teterboro Airport just outside of Manhattan.

This creates an empty leg flight from Chicago to NYC, and clients looking to arrive in NY from Chicago, Indianapolis, Detroit, Pittsburgh, Cleveland, or any city on the way can arrange for the plane to stop and pick them up at just a fraction of the cost.

Whenever a private plane flies empty, owners and operators don’t make any money. Since it’s flying anyway in this case, charter operators will discount the empty flight, and that’s where the savings come from—filling an empty plane can save you up to 50 percent (or more) on your total charter cost!

Find an Empty Leg in Chicago, IL

Looking for the best deal for your next private flight to/from Chicago? The demand for empty legs continues to grow, with brokers, operators, and travel concierges saturating the market with offers, often just to get your attention. Searching for one on your own can be frustrating, as availability is limited, operators are limited to their own fleets, and the deals are first come, first serve.

Instead, you can find the best deals on an empty leg to/from Chicago by giving us a call anytime, anywhere—just give us your trip details, and we’ll find one for you!

Our company enjoys access to all of the transient charter planes available across the United States and around the world. We’ll search through aircraft schedules to find deals that match your flight’s routing. We also compare empty leg costs for different aircraft from different operators so you always get the best price.

Are you a flexible traveler? The more open you are with the dates, times, and airports used for your flight, the most options you’ll have when looking for a deal. Aircraft schedules can change by the hour as new flights are booked. Even if we can’t find an empty leg near you, we still offer the best air charter services in Chicago with the competitive rates and the highest levels of safety & service.

Whether you’re looking for the best price on a one-way flight to/from Chicago or a short hop within the Midwest, let us locate a transient aircraft that can work for your trip, and save on the cost of private jet travel!

Popular Routes

Chicago to New York, NY
Chicago to Las Vegas, NV

Request a Quote | Empty Leg Jet Charters

Find deals on deadhead air charters in Chicago no matter where you’re located. Our services are available 24 hours a day, 7 days a week, and quotes from us cost nothing and come with no commitments. Contact us to get more information on empty legs to/from Chicago, IL!