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:
Allentown, Lehigh Valley International (ABE), PA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
04.08.2025
Aircraft:
Learjet 60
Capacity:
7
$6,608
Distance between ABE - MDW:
644 mi (1036 km)
Estimated flight duration:
1 hours : 19 minutes
Cost per person:
$943.93
Cost per hour:
$4960.01
Learjet 60 image 1
Learjet 60 image 2

From:
Scottsdale, Scottsdale Airport (SDL), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
05.08.2025
Aircraft:
Learjet 45
Capacity:
9
$17,174
Distance between SDL - MDW:
4143 mi (6668 km)
Estimated flight duration:
8 hours : 17 minutes
Cost per person:
$1908.22
Cost per hour:
$2070.83
Learjet 45 image 1
Learjet 45 image 2

From:
Seattle, seattle airport (SEA), WA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
06.08.2025
Aircraft:
Beechjet 400A
Capacity:
8
$21,706
Distance between SEA - MDW:
1731 mi (2786 km)
Cost per person:
$2713.28
Cost per hour:
$2617.33

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
10.08.2025
Aircraft:
Citation V
Capacity:
7
$11,342
Distance between APF - PWK:
1157 mi (1861 km)
Cost per person:
$1620.33
Cost per hour:
$1367.65

From:
Nashville, Nashville International Airport (BNA), TN, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Departure date:
11.08.2025
Aircraft:
Citation XLS+
Capacity:
8
$4,382
Distance between BNA - UGN:
435 mi (701 km)
Estimated flight duration:
0 hours : 51 minutes
Cost per person:
$547.78
Cost per hour:
$5103.47
Citation XLS+ image 1
Citation XLS+ image 2

From:
Islip, Long Island Mac Arthur (ISP), NY, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
18.08.2025
Aircraft:
Hawker 400XP
Capacity:
8
$10,853
Distance between ISP - MDW:
763 mi (1227 km)
Estimated flight duration:
1 hours : 29 minutes
Cost per person:
$1356.64
Cost per hour:
$7251.07
Hawker 400XP image 1
Hawker 400XP image 2

From:
Boca Raton, Boca Raton Airport (BCT), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
20.08.2025
Aircraft:
Hawker 400XP
Capacity:
8
$13,024
Distance between BCT - MDW:
1152 mi (1854 km)
Estimated flight duration:
2 hours : 15 minutes
Cost per person:
$1627.94
Cost per hour:
$5758.8
Hawker 400XP image 1
Hawker 400XP image 2

From:
Oakland, Metropolitan Oakland International (OAK), CA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
21.08.2025
Aircraft:
Hawker 400XP
Capacity:
7
$19,465
Distance between OAK - MDW:
1842 mi (2964 km)
Estimated flight duration:
3 hours : 36 minutes
Cost per person:
$2780.73
Cost per hour:
$5385.64
Hawker 400XP image 1
Hawker 400XP image 2

From:
Dallas, Addison (ADS), TX, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
01.09.2025
Aircraft:
Learjet 45
Capacity:
9
$13,214
Distance between ADS - MDW:
814 mi (1309 km)
Estimated flight duration:
1 hours : 37 minutes
Cost per person:
$1468.2
Cost per hour:
$8114.61
Learjet 45 image 1
Learjet 45 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Boston, General Edward Lawrence Logan International (BOS), MA, US
Departure date:
04.08.2025
Aircraft:
Beechjet 400A
Capacity:
8
$12,051
Distance between MDW - BOS:
855 mi (1376 km)
Cost per person:
$1506.4
Cost per hour:
$7400.62

From:
Chicago, Midway International (MDW), IL, US
To:
Omaha, Eppley Airfield (OMA), NE, US
Departure date:
04.08.2025
Aircraft:
Hawker 400XP
Capacity:
8
$7,669
Distance between MDW - OMA:
429 mi (690 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$958.62
Cost per hour:
$9114.57
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Executive (PWK), IL, US
To:
Hazleton, Municipal (HZL), PA, US
Departure date:
09.08.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$13,885
Distance between PWK - HZL:
620 mi (998 km)
Cost per person:
$867.8
Cost per hour:
$16502.22

From:
Chicago, Executive (PWK), IL, US
To:
Houston, William P Hobby (HOU), TX, US
Departure date:
10.08.2025
Aircraft:
Citation V
Capacity:
7
$10,518
Distance between PWK - HOU:
954 mi (1535 km)
Cost per person:
$1502.52
Cost per hour:
$12500.28

From:
Chicago, Midway International (MDW), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
10.08.2025
Aircraft:
Citation X
Capacity:
8
$9,921
Distance between MDW - TEB:
712 mi (1146 km)
Estimated flight duration:
1 hours : 10 minutes
Cost per person:
$1240.13
Cost per hour:
$8465.22
Citation X image 1
Citation X image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Miami, Opa-locka Executive (OPF), FL, US
Departure date:
11.08.2025
Aircraft:
Gulfstream G-IVSP
Capacity:
12
$27,035
Distance between MDW - OPF:
1177 mi (1895 km)
Cost per person:
$2252.93
Cost per hour:
$23068.03

From:
Chicago, Midway International (MDW), IL, US
To:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
Departure date:
12.08.2025
Aircraft:
Beechjet 400A
Capacity:
8
$17,365
Distance between MDW - BZN:
1196 mi (1925 km)
Cost per person:
$2170.69
Cost per hour:
$14817.25

From:
Chicago, Midway International (MDW), IL, US
To:
Bedford, Laurence G Hanscom Field (BED), MA, US
Departure date:
15.08.2025
Aircraft:
Hawker 400XP
Capacity:
8
$13,097
Distance between MDW - BED:
843 mi (1357 km)
Estimated flight duration:
1 hours : 39 minutes
Cost per person:
$1637.09
Cost per hour:
$7913.97
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Executive (PWK), IL, US
To:
Ft Lauderdale, Fort Lauderdale Executive (FXE), FL, US
Departure date:
19.08.2025
Aircraft:
Beechjet 400A
Capacity:
7
$9,226
Distance between PWK - FXE:
1193 mi (1920 km)
Cost per person:
$1317.95
Cost per hour:
$5574.79

From:
Chicago, Dupage (DPA), IL, US
To:
White Plains, Westchester County (HPN), NY, US
Departure date:
21.08.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$15,930
Distance between DPA - HPN:
754 mi (1214 km)
Cost per person:
$995.6
Cost per hour:
$9625.77

From:
Chicago, Midway International (MDW), IL, US
To:
Westhampton Beach, Francis S Gabreski (FOK), NY, US
Departure date:
23.08.2025
Aircraft:
Hawker 400XP
Capacity:
8
$12,525
Distance between MDW - FOK:
784 mi (1262 km)
Estimated flight duration:
1 hours : 32 minutes
Cost per person:
$1565.57
Cost per hour:
$8136.43
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Dallas, Addison (ADS), TX, US
Departure date:
27.08.2025
Aircraft:
Learjet 45
Capacity:
9
$15,338
Distance between MDW - ADS:
814 mi (1309 km)
Estimated flight duration:
1 hours : 37 minutes
Cost per person:
$1704.2
Cost per hour:
$9418.97
Learjet 45 image 1
Learjet 45 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Sarasota, Bradenton International (SRQ), FL, US
Departure date:
30.08.2025
Aircraft:
Hawker 400XP
Capacity:
8
$13,228
Distance between MDW - SRQ:
1038 mi (1670 km)
Estimated flight duration:
2 hours : 2 minutes
Cost per person:
$1653.56
Cost per hour:
$6496.18
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Westhampton Beach, Francis S Gabreski (FOK), NY, US
Departure date:
30.08.2025
Aircraft:
Beechjet 400A
Capacity:
8
$11,024
Distance between MDW - FOK:
784 mi (1262 km)
Cost per person:
$1377.99
Cost per hour:
$5413.58

From:
Greenville, Downtown (GMU), SC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$9,661
Distance between GMU - MDW:
560 mi (902 km)
Estimated flight duration:
1 hours : 5 minutes
Cost per person:
$1207.65
Cost per hour:
$8784.66
Hawker 400XP image 1
Hawker 400XP image 2

From:
Nashville, John C Tune (JWN), TN, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 900EX
Capacity:
12
$14,297
Distance between JWN - DPA:
6352 mi (10222 km)
Estimated flight duration:
10 hours : 45 minutes
Cost per person:
$1191.43
Cost per hour:
$1328.67
Falcon 900EX image 1
Falcon 900EX image 2

From:
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 900EX
Capacity:
12
$14,112
Distance between BNA - DPA:
409 mi (657 km)
Estimated flight duration:
0 hours : 41 minutes
Cost per person:
$1175.98
Cost per hour:
$20391.52
Falcon 900EX image 1
Falcon 900EX image 2

From:
Bedford, Laurence G Hanscom Field (BED), MA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$12,881
Distance between BED - MDW:
843 mi (1357 km)
Estimated flight duration:
1 hours : 39 minutes
Cost per person:
$1610.1
Cost per hour:
$7783.48
Hawker 400XP image 1
Hawker 400XP image 2

From:
Nashville, John C Tune (JWN), TN, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 900EX
Capacity:
12
$14,297
Distance between JWN - DPA:
6352 mi (10222 km)
Estimated flight duration:
10 hours : 45 minutes
Cost per person:
$1191.43
Cost per hour:
$1328.67
Falcon 900EX image 1
Falcon 900EX image 2

From:
Westhampton Beach, Francis S Gabreski (FOK), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$11,270
Distance between FOK - MDW:
784 mi (1262 km)
Estimated flight duration:
1 hours : 32 minutes
Cost per person:
$1408.8
Cost per hour:
$7321.68
Hawker 400XP image 1
Hawker 400XP image 2

From:
Albany, Albany International Airport (ALB), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$10,956
Distance between ALB - MDW:
717 mi (1155 km)
Estimated flight duration:
1 hours : 24 minutes
Cost per person:
$1369.45
Cost per hour:
$7780.71
Hawker 400XP image 1
Hawker 400XP image 2

From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 40
Capacity:
6
$9,800
Distance between PIE - MDW:
1000 mi (1610 km)
Estimated flight duration:
1 hours : 53 minutes
Cost per person:
$1633.38
Cost per hour:
$5186.75
Learjet 40 image 1
Learjet 40 image 2

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
9
$10,419
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$1157.64
Cost per hour:
$12322.43
Citation XLS image 1
Citation XLS image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Legacy 500
Capacity:
9
$16,336
Distance between OPF - PWK:
1201 mi (1933 km)
Estimated flight duration:
2 hours : 14 minutes
Cost per person:
$1815.09
Cost per hour:
$7291.98
Legacy 500 image 1
Legacy 500 image 2

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Beechjet 400A
Capacity:
8
$7,948
Distance between OMA - DPA:
403 mi (649 km)
Cost per person:
$993.54
Cost per hour:
$3547.96

From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G-V
Capacity:
16
$7,990
Distance between MSP - PWK:
334 mi (537 km)
Cost per person:
$499.36
Cost per hour:
$3566.48

From:
Southern Pines, Moore County (SOP), NC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$10,776
Distance between SOP - MDW:
639 mi (1028 km)
Estimated flight duration:
1 hours : 15 minutes
Cost per person:
$1539.47
Cost per hour:
$8594.24
Hawker 400XP image 1
Hawker 400XP image 2

From:
Brookshire, Houston Executive (TME), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$12,932
Distance between TME - MDW:
2629 mi (4230 km)
Estimated flight duration:
5 hours : 9 minutes
Cost per person:
$1616.5
Cost per hour:
$2506.72
Hawker 400XP image 1
Hawker 400XP image 2

From:
Bristol, Tri Cities Regional Tn Va (TRI), TN, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
9
$12,922
Distance between TRI - MDW:
465 mi (748 km)
Estimated flight duration:
0 hours : 55 minutes
Cost per person:
$1435.8
Cost per hour:
$14095.62
Citation XLS image 1
Citation XLS image 2

From:
Minneapolis, Anoka County-Blaine Arpt(Janes Field) (ANE), MN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation CJ3
Capacity:
8
$10,268
Distance between ANE - PWK:
4066 mi (6544 km)
Estimated flight duration:
8 hours : 29 minutes
Cost per person:
$1283.44
Cost per hour:
$1208.17
Citation CJ3 image 1
Citation CJ3 image 2

From:
Denver, Centennial (APA), CO, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$13,043
Distance between APA - MDW:
912 mi (1468 km)
Estimated flight duration:
1 hours : 47 minutes
Cost per person:
$1863.29
Cost per hour:
$7285.93
Hawker 400XP image 1
Hawker 400XP image 2

From:
Port Hawkesbury, Port Hawkesbury Airport (YPS), NS, CA
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G-V
Capacity:
16
$27,531
Distance between YPS - DPA:
1360 mi (2189 km)
Cost per person:
$1720.66
Cost per hour:
$15378.75

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
13
$17,911
Distance between TEB - PWK:
721 mi (1160 km)
Cost per person:
$1377.76
Cost per hour:
$10005.12

From:
Kearney, Kearney Regional Airport (EAR), NE, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Nextant 400XTi
Capacity:
8
$12,592
Distance between EAR - GYY:
605 mi (974 km)
Cost per person:
$1573.95
Cost per hour:
$7033.77

From:
Cleveland, Hopkins International (CLE), OH, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Bravo
Capacity:
7
$11,588
Distance between CLE - MDW:
313 mi (503 km)
Cost per person:
$1655.37
Cost per hour:
$6472.9

From:
Van Nuys, Van Nuys Airport (VNY), CA, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 900B
Capacity:
14
$30,185
Distance between VNY - DPA:
1720 mi (2768 km)
Cost per person:
$2156.09
Cost per hour:
$16861.7

From:
Orlando, Executive (ORL), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$12,914
Distance between ORL - MDW:
983 mi (1582 km)
Estimated flight duration:
1 hours : 55 minutes
Cost per person:
$1614.21
Cost per hour:
$6692.62
Hawker 400XP image 1
Hawker 400XP image 2

From:
Stuart, Witham Field (SUA), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$12,881
Distance between SUA - MDW:
1094 mi (1760 km)
Estimated flight duration:
2 hours : 8 minutes
Cost per person:
$1840.11
Cost per hour:
$6000.94
Hawker 400XP image 1
Hawker 400XP image 2

From:
Dallas, Love Field (DAL), TX, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 900B
Capacity:
14
$17,542
Distance between DAL - DPA:
784 mi (1262 km)
Cost per person:
$1253.03
Cost per hour:
$8172.71

From:
Panama City, Northwest Florida Beaches International (ECP), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
7
$9,686
Distance between ECP - MDW:
797 mi (1283 km)
Cost per person:
$1383.65
Cost per hour:
$4512.36

From:
Jerome, County (JER), ID, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Ultra
Capacity:
8
$13,050
Distance between JER - PWK:
3943 mi (6345 km)
Estimated flight duration:
7 hours : 58 minutes
Cost per person:
$1631.29
Cost per hour:
$1637.2
Citation Ultra image 1
Citation Ultra image 2

From:
White Plains, Westchester County (HPN), NY, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 900B
Capacity:
14
$17,512
Distance between HPN - DPA:
754 mi (1214 km)
Cost per person:
$1250.85
Cost per hour:
$2196.92

From:
Hailey, Friedman Memorial (SUN), ID, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Ultra
Capacity:
8
$13,050
Distance between SUN - PWK:
1338 mi (2153 km)
Estimated flight duration:
2 hours : 42 minutes
Cost per person:
$1631.29
Cost per hour:
$4825.14
Citation Ultra image 1
Citation Ultra image 2

From:
Knoxville, McGhee Tyson (TYS), TN, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Nextant 400XTi
Capacity:
8
$10,440
Distance between TYS - GYY:
442 mi (711 km)
Cost per person:
$1304.94
Cost per hour:
$3859.84

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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