Empty Leg Flights to and from Chicago
Looking for great deals on empty leg flights to or from Chicago? Take advantage of private jet savings with one-way and return empty leg flights. Whether you're heading to Chicago (CHI) or departing from it, book your next flight today and enjoy luxurious, cost-effective travel.
Miami, Opa-locka Executive (OPF), FL, US
Chicago, Midway International (MDW), IL, US
01.11.2025
Hawker 400XP
7
Omaha, Eppley Airfield (OMA), NE, US
Chicago, Midway International (MDW), IL, US
02.11.2025
Beechjet 400A
8
Omaha, Eppley Airfield (OMA), NE, US
Chicago, Executive (PWK), IL, US
02.11.2025
Beechjet 400A
8
Sarasota, Bradenton International (SRQ), FL, US
Chicago, Midway International (MDW), IL, US
03.11.2025
Learjet 45
9
Nashville, Nashville International Airport (BNA), TN, US
Chicago, Executive (PWK), IL, US
03.11.2025
Learjet 45
9
Memphis, Memphis International Airport (MEM), TN, US
Chicago, Executive (PWK), IL, US
03.11.2025
Challenger 300
10
West Palm Beach, Palm Beach International (PBI), FL, US
Chicago, Midway International (MDW), IL, US
05.11.2025
Hawker 400XP
8
Tucson, Tucson International Airport (TUS), AZ, US
Chicago, Executive (PWK), IL, US
06.11.2025
Learjet 45
9
Marco, Island (MKY), FL, US
Chicago, Midway International (MDW), IL, US
07.11.2025
Learjet 45
9
Palm Springs, Palm Springs International Airport (PSP), CA, US
Chicago, Midway International (MDW), IL, US
08.11.2025
Hawker 400XP
8
Dallas, Addison (ADS), TX, US
Chicago, Midway International (MDW), IL, US
10.11.2025
Hawker 400XP
7
Stuart, Witham Field (SUA), FL, US
Chicago, Executive (PWK), IL, US
11.11.2025
Citation Ultra
7
Charleston, Executive (JZI), SC, US
Chicago, Executive (PWK), IL, US
12.11.2025
Hawker 400XP
8
Flagstaff, Pulliam (FLG), AZ, US
Chicago, Midway International (MDW), IL, US
14.11.2025
Hawker 400XP
7
Chicago, Executive (PWK), IL, US
Buffalo, Niagara International (BUF), NY, US
03.11.2025
Gulfstream G200
9
Chicago, Midway International (MDW), IL, US
Missoula, Missoula International Airport (MSO), MT, US
03.11.2025
Hawker 400XP
8
Chicago, Midway International (MDW), IL, US
Teterboro, Teterboro Airport (TEB), NJ, US
03.11.2025
Beechjet 400A
8
Chicago, Executive (PWK), IL, US
Cincinnati, Municipal Airport Lunken Field (LUK), OH, US
04.11.2025
Citation Ultra
7
Chicago, Midway International (MDW), IL, US
Dallas, Addison (ADS), TX, US
06.11.2025
Hawker 400XP
8
Chicago, Midway International (MDW), IL, US
Naples, Municipal (APF), FL, US
06.11.2025
Beechjet 400A
8
Chicago, Midway International (MDW), IL, US
Savannah, Hilton Head International (SAV), GA, US
08.11.2025
Beechjet 400A
8
Chicago, Midway International (MDW), IL, US
Starkville, George M Bryan (STF), MS, US
08.11.2025
Hawker 400XP
7
Chicago, Executive (PWK), IL, US
Stuart, Witham Field (SUA), FL, US
10.11.2025
Citation Ultra
7
Chicago, Executive (PWK), IL, US
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
10.11.2025
Citation CJ4 Gen2
8
Chicago, Midway International (MDW), IL, US
Scottsdale, Scottsdale Airport (SDL), AZ, US
11.11.2025
Learjet 45
9
Chicago, Midway International (MDW), IL, US
White Plains, Westchester County (HPN), NY, US
11.11.2025
Hawker 400XP
8
Chicago, Midway International (MDW), IL, US
Islip, Long Island Mac Arthur (ISP), NY, US
13.11.2025
Hawker 400XP
7
Chicago, Midway International (MDW), IL, US
Marco, Island (MKY), FL, US
14.11.2025
Learjet 45
9
Chicago, Midway International (MDW), IL, US
West Palm Beach, Palm Beach International (PBI), FL, US
20.11.2025
Citation CJ1+
5
Chicago, Executive (PWK), IL, US
St Louis, Lambert St Louis International (STL), MO, US
25.11.2025
Challenger 300
10
Jacksonville, Jacksonville International Airport (JAX), FL, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
7
Buffalo, Niagara International (BUF), NY, US
Chicago, Midway International (MDW), IL, US
Beechjet 400A
8
Rochester, Greater Rochester International (ROC), NY, US
Chicago, Executive (PWK), IL, US
Learjet 45
9
Panama City, Northwest Florida Beaches International (ECP), FL, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
7
Scottsdale, Scottsdale Airport (SDL), AZ, US
Chicago, Midway International (MDW), IL, US
Gulfstream G-IV
14
Venice, Municipal (VNC), FL, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
7
South Lake Tahoe, Lake Tahoe (TVL), CA, US
Chicago, Midway International (MDW), IL, US
Learjet 45
9
Chesterfield, Spirit of St Louis (SUS), MO, US
Chicago, Executive (PWK), IL, US
Hawker 900XP
8
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
Chicago, Executive (PWK), IL, US
Citation CJ4 Gen2
8
Denver, Centennial (APA), CO, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
8
Tucson, Tucson International Airport (TUS), AZ, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
8
Teterboro, Teterboro Airport (TEB), NJ, US
Chicago, Midway International (MDW), IL, US
Citation Latitude
9
Miami, Opa-locka Executive (OPF), FL, US
Chicago, Midway International (MDW), IL, US
Citation Latitude
9
Jacksonville, Jacksonville International Airport (JAX), FL, US
Chicago, Dupage (DPA), IL, US
Hawker 400XP
7
Scottsdale, Scottsdale Airport (SDL), AZ, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
8
East St. Louis, St Louis Downtown (CPS), IL, US
Chicago, Executive (PWK), IL, US
Citation III
9
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
Chicago, Dupage (DPA), IL, US
Citation X
8
Naples, Municipal (APF), FL, US
Chicago, Executive (PWK), IL, US
Citation Sovereign
8
Oklahoma City, Will Rogers World (OKC), OK, US
Chicago, Executive (PWK), IL, US
Gulfstream G-IV
14
Sarasota, Bradenton International (SRQ), FL, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
7
Rochester, Greater Rochester International (ROC), NY, US
Chicago, Executive (PWK), IL, US
Falcon 900EX
13
Nashville, Nashville International Airport (BNA), TN, US
Chicago, Executive (PWK), IL, US
Falcon 900B
14
West Palm Beach, Palm Beach International (PBI), FL, US
Chicago, Executive (PWK), IL, US
Citation CJ3+
6
Ft Myers, Southwest Florida International (RSW), FL, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
8
Teterboro, Teterboro Airport (TEB), NJ, US
Chicago, Dupage (DPA), IL, US
Gulfstream G200
9
Teterboro, Teterboro Airport (TEB), NJ, US
Chicago, Executive (PWK), IL, US
Citation Latitude
9
Tucson, Tucson International Airport (TUS), AZ, US
Chicago, Midway International (MDW), IL, US
Hawker 400XP
8
Miami, Opa-locka Executive (OPF), FL, US
Chicago, Executive (PWK), IL, US
Citation Latitude
9
New Orleans, Louis Armstrong New Orleans International (MSY), LA, US
Chicago, Midway International (MDW), IL, US
Falcon 900EX
13
Omaha, Eppley Airfield (OMA), NE, US
Chicago, Midway International (MDW), IL, US
Learjet 60
8
Benefits of Booking Empty Leg Flights in Chicago
Booking an empty leg flight in Chicago can offer numerous benefits to travelers. One major advantage is the potential for significant cost savings. Since these flights are often operated at a lower cost than standard charter flights, passengers can enjoy a more affordable option without compromising on luxury or convenience. Another benefit is flexibility – empty leg flights can provide a flexible schedule that allows travelers to book a flight that suits their needs, even if it's not during peak travel hours. Additionally, these flights often offer a unique and exclusive travel experience, complete with amenities like gourmet catering, comfortable seating, and personalized service.
Statistics and Market Trends in Chicago
A growing demand for private jet travel has led to an increase in empty leg flights in Chicago. According to recent statistics, the number of private flights in the United States has seen a significant surge over the past few years, with Chicago being one of the busiest hubs. In fact, a study by the General Aviation Manufacturers Association found that private jet travel is experiencing steady growth, with many industry experts predicting continued expansion in the coming years. Furthermore, the rise of on-demand charter services and online booking platforms has made it easier for passengers to find and book empty leg flights, further fueling market demand.
How to Find the Best Deals on Empty Leg Flights in Chicago
To find the best deals on empty leg flights in Chicago, travelers can try the following:
- Maintain a flexible schedule and be open to different flight dates and times.
- Use online platforms or apps that specialize in private jet travel, such as JetSmarter or Victor.
- Contact local brokers or charter companies, who often have access to a wider range of empty leg flights.
Popular Routes from Chicago
Some popular empty leg flight routes from Chicago include:
- Chicago to Miami: This route is in high demand due to the city's thriving business community and the popularity of South Florida as a vacation destination.
- Chicago to New York City: As one of the most populous cities in the United States, NYC is a major hub for private jet travel, with many empty leg flights available from Chicago.
- Chicago to Los Angeles: This route is popular among entertainment industry professionals and business travelers looking to access LA's bustling airports and surrounding communities.
Local Airports and Private Jet Terminals in Chicago
In Chicago, there are several local airports and private jet terminals that serve empty leg flights. One notable option is the Pal-Waukee Airport (KPWA), a popular alternative to O'Hare International Airport for private aviation travelers. The airport offers amenities like fuel services, hangar space, and ground transportation, making it an ideal location for those seeking empty leg flights.
Frequently Asked Questions
Are empty leg flights in Chicago always cheaper?
No, empty leg flights in Chicago are not always cheaper. While these flights can offer significant cost savings compared to standard charter flights, prices may still vary depending on factors like the distance of the flight, the type of aircraft, and the level of service required. However, by being flexible with your travel dates and times, you may be able to find a more affordable option.
Can I choose the exact departure time?
While empty leg flights often have fixed schedules due to their unique nature, some brokers or charter companies may offer flexibility in terms of departure time. However, this is not always possible, as the flight's itinerary and schedule are often determined by the original booking. In certain cases, you may be able to negotiate a revised departure time or find alternative flights that better suit your needs.


