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.

From:
Madrid (MAD)
To:
Chicago (CHI)
Departure date:
21.03.2026
Aircraft:
Gulfstream G350
Capacity:
16
$38,542
Distance between MAD - CHI:
4180 mi (6727 km)
Estimated flight duration:
7 hours : 26 minutes
Cost per person:
$2408.86
Cost per hour:
$5173.67
Gulfstream G350 image 1
Gulfstream G350 image 2

From:
Harbin (HRB)
To:
Chicago (CHI)
Departure date:
01.03.2026
Aircraft:
Falcon 7X
Capacity:
16
$75,769
Distance between HRB - CHI:
6043 mi (9725 km)
Estimated flight duration:
11 hours : 26 minutes
Cost per person:
$4735.57
Cost per hour:
$6622.5
Falcon 7X image 1
Falcon 7X image 2

From:
Dehra Dun (DED)
To:
Chicago (CHI)
Departure date:
21.03.2026
Aircraft:
Falcon 8X
Capacity:
16
$157,595
Distance between DED - CHI:
7368 mi (11857 km)
Estimated flight duration:
13 hours : 56 minutes
Cost per person:
$9849.66
Cost per hour:
$11297.58
Falcon 8X image 1
Falcon 8X image 2

From:
Milan (MIL)
To:
Chicago (CHI)
Departure date:
03.03.2026
Aircraft:
Falcon 900
Capacity:
19
$46,121
Distance between MIL - CHI:
4530 mi (7291 km)
Estimated flight duration:
7 hours : 40 minutes
Cost per person:
$2427.44
Cost per hour:
$6009.49
Falcon 900 image 1
Falcon 900 image 2

From:
Wroclaw (WRO)
To:
Chicago (CHI)
Departure date:
22.03.2026
Aircraft:
Falcon 900
Capacity:
19
$46,623
Distance between WRO - CHI:
4581 mi (7372 km)
Estimated flight duration:
7 hours : 45 minutes
Cost per person:
$2453.82
Cost per hour:
$6008.07
Falcon 900 image 1
Falcon 900 image 2

From:
Chicago, Executive (PWK), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
02.03.2026
Aircraft:
Challenger 300
Capacity:
8
$12,895
Distance between PWK - TEB:
721 mi (1160 km)
Estimated flight duration:
1 hours : 21 minutes
Cost per person:
$1611.93
Cost per hour:
$9445.65
Challenger 300 image 1
Challenger 300 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Bedford, Laurence G Hanscom Field (BED), MA, US
Departure date:
14.03.2026
Aircraft:
Citation Excel
Capacity:
8
$15,050
Distance between MDW - BED:
843 mi (1357 km)
Cost per person:
$1881.24
Cost per hour:
$11023.8

From:
Clarinda, Schenck Field (ICL), IA, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Nextant 400XTi
Capacity:
8
$9,191
Distance between ICL - GYY:
401 mi (645 km)
Cost per person:
$1148.94
Cost per hour:
$6732.59

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
13
$10,693
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$822.56
Cost per hour:
$7832.65

From:
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
10
$7,737
Distance between SUS - PWK:
266 mi (428 km)
Estimated flight duration:
0 hours : 30 minutes
Cost per person:
$773.72
Cost per hour:
$15351.77
Challenger 300 image 1
Challenger 300 image 2

From:
Nashville, John C Tune (JWN), TN, US
To:
Chicago, Lewis University (LOT), IL, US
Aircraft:
Citation Excel
Capacity:
9
$5,928
Distance between JWN - LOT:
6365 mi (10244 km)
Cost per person:
$658.66
Cost per hour:
$11761.95

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45XR
Capacity:
8
$8,492
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 51 minutes
Cost per person:
$1061.55
Cost per hour:
$9896.37
Learjet 45XR image 1
Learjet 45XR image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation Excel
Capacity:
13
$18,185
Distance between OPF - DPA:
1196 mi (1925 km)
Cost per person:
$1398.87
Cost per hour:
$21191.68

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 800XPi
Capacity:
6
$20,325
Distance between APF - MDW:
1133 mi (1823 km)
Cost per person:
$3387.53
Cost per hour:
$23685.32

From:
Stuart, Witham Field (SUA), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS
Capacity:
9
$15,435
Distance between SUA - PWK:
1118 mi (1799 km)
Estimated flight duration:
2 hours : 12 minutes
Cost per person:
$1715.05
Cost per hour:
$7002.95
Citation XLS image 1
Citation XLS image 2

From:
Atlanta, Hartsfield Jackson Atlanta International (ATL), GA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$8,590
Distance between ATL - MDW:
585 mi (941 km)
Estimated flight duration:
1 hours : 8 minutes
Cost per person:
$1073.75
Cost per hour:
$7483.16
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS
Capacity:
8
$8,590
Distance between SUS - UGN:
283 mi (456 km)
Estimated flight duration:
0 hours : 33 minutes
Cost per person:
$1073.75
Cost per hour:
$15384.17
Citation XLS image 1
Citation XLS image 2

From:
Hazleton, Municipal (HZL), PA, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Gulfstream G-V
Capacity:
16
$16,614
Distance between HZL - GYY:
594 mi (957 km)
Cost per person:
$1038.37
Cost per hour:
$29754.53

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Hawker 850XP
Capacity:
8
$18,865
Distance between APF - DPA:
1150 mi (1850 km)
Estimated flight duration:
2 hours : 29 minutes
Cost per person:
$2358.11
Cost per hour:
$7595.57
Hawker 850XP image 1
Hawker 850XP image 2

From:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Capacity:
6
$13,374
Distance between BZN - MDW:
1196 mi (1925 km)
Estimated flight duration:
2 hours : 29 minutes
Cost per person:
$2228.94
Cost per hour:
$5350.22
Citation CJ3 image 1
Citation CJ3 image 2

From:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Capacity:
6
$13,398
Distance between BZN - MDW:
1196 mi (1925 km)
Estimated flight duration:
2 hours : 29 minutes
Cost per person:
$2233.01
Cost per hour:
$5359.98
Citation CJ3 image 1
Citation CJ3 image 2

From:
Naples, Municipal (APF), FL, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS
Capacity:
9
$15,512
Distance between APF - UGN:
1172 mi (1886 km)
Estimated flight duration:
2 hours : 18 minutes
Cost per person:
$1723.59
Cost per hour:
$6711.23
Citation XLS image 1
Citation XLS image 2

From:
Sanford, Orlando Sanford International (SFB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G500
Capacity:
14
$25,054
Distance between SFB - MDW:
970 mi (1562 km)
Estimated flight duration:
1 hours : 38 minutes
Cost per person:
$1789.57
Cost per hour:
$15336.18
Gulfstream G500 image 1
Gulfstream G500 image 2

From:
Jackson Hole, Jackson Hole Airport (JAC), WY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Ultra
Capacity:
7
$9,709
Distance between JAC - MDW:
1171 mi (1885 km)
Estimated flight duration:
2 hours : 22 minutes
Cost per person:
$1386.97
Cost per hour:
$4100.86
Citation Ultra image 1
Citation Ultra image 2

From:
Scottsdale, Scottsdale Airport (SDL), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$16,740
Distance between SDL - MDW:
4143 mi (6668 km)
Estimated flight duration:
8 hours : 7 minutes
Cost per person:
$2092.45
Cost per hour:
$2058.62
Hawker 400XP image 1
Hawker 400XP image 2

From:
Denver, Centennial (APA), CO, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$13,392
Distance between APA - MDW:
912 mi (1468 km)
Estimated flight duration:
1 hours : 47 minutes
Cost per person:
$1673.99
Cost per hour:
$7480.84
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Capacity:
9
$19,530
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 21 minutes
Cost per person:
$2169.97
Cost per hour:
$14305.2
Gulfstream G200 image 1
Gulfstream G200 image 2

From:
White Plains, Westchester County (HPN), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$11,173
Distance between HPN - MDW:
728 mi (1172 km)
Estimated flight duration:
1 hours : 25 minutes
Cost per person:
$1596.11
Cost per hour:
$7816.81
Hawker 400XP image 1
Hawker 400XP image 2

From:
Tulsa, Tulsa International Airport (TUL), OK, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
10
$12,778
Distance between TUL - PWK:
598 mi (962 km)
Estimated flight duration:
1 hours : 7 minutes
Cost per person:
$1277.83
Cost per hour:
$11292.51
Challenger 300 image 1
Challenger 300 image 2

From:
Norfolk, Norfolk International Airport (ORF), VA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$10,614
Distance between ORF - MDW:
700 mi (1127 km)
Estimated flight duration:
1 hours : 22 minutes
Cost per person:
$1326.75
Cost per hour:
$7723.03
Hawker 400XP image 1
Hawker 400XP image 2

From:
Morristown, Municipal (MMU), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$11,173
Distance between MMU - MDW:
695 mi (1118 km)
Estimated flight duration:
1 hours : 21 minutes
Cost per person:
$1396.6
Cost per hour:
$8195.89
Hawker 400XP image 1
Hawker 400XP image 2

From:
Quebec, Jean Lesage International (YQB), QC, CA
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Capacity:
9
$16,109
Distance between YQB - MDW:
884 mi (1423 km)
Estimated flight duration:
1 hours : 46 minutes
Cost per person:
$1789.88
Cost per hour:
$9098.9
Learjet 45 image 1
Learjet 45 image 2

From:
Dallas, Addison (ADS), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$11,173
Distance between ADS - MDW:
814 mi (1309 km)
Estimated flight duration:
1 hours : 35 minutes
Cost per person:
$1396.6
Cost per hour:
$6997.74
Hawker 400XP image 1
Hawker 400XP image 2

From:
Charlevoix, Municipal (CVX), MI, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation Excel
Capacity:
9
$4,464
Distance between CVX - DPA:
6130 mi (9865 km)
Cost per person:
$496
Cost per hour:
$2795.89

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Capacity:
9
$9,598
Distance between OMA - PWK:
422 mi (679 km)
Estimated flight duration:
0 hours : 47 minutes
Cost per person:
$1066.42
Cost per hour:
$12013.59
Gulfstream G200 image 1
Gulfstream G200 image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS+
Capacity:
8
$21,204
Distance between OPF - MDW:
1177 mi (1895 km)
Estimated flight duration:
2 hours : 19 minutes
Cost per person:
$2650.45
Cost per hour:
$9131.52
Citation XLS+ image 1
Citation XLS+ image 2

From:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
IAI Astra SPX
Capacity:
7
$16,759
Distance between FLL - PWK:
1190 mi (1915 km)
Cost per person:
$2394.16
Cost per hour:
$7217.48

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.

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