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:
Farmingdale, Republic (FRG), NY, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
05.06.2025
Aircraft:
Learjet 60
Capacity:
7
$7,608
Distance between FRG - MDW:
747 mi (1202 km)
Estimated flight duration:
1 hours : 32 minutes
Cost per person:
$1086.85
Cost per hour:
$4924.35
Learjet 60 image 1
Learjet 60 image 2

From:
Ames, Municipal (AMW), IA, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
06.06.2025
Aircraft:
Citation Excel
Capacity:
7
$5,395
Distance between AMW - PWK:
293 mi (472 km)
Cost per person:
$770.69
Cost per hour:
$3491.9

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
07.06.2025
Aircraft:
Citation Ultra
Capacity:
8
$15,786
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 26 minutes
Cost per person:
$1973.2
Cost per hour:
$10962.65
Citation Ultra image 1
Citation Ultra image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
07.06.2025
Aircraft:
Challenger 300
Capacity:
8
$14,996
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1874.53
Cost per hour:
$11120.99
Challenger 300 image 1
Challenger 300 image 2

From:
New Haven, Tweed New Haven (HVN), CT, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
07.06.2025
Aircraft:
Citation Ultra
Capacity:
8
$15,705
Distance between HVN - MDW:
766 mi (1233 km)
Estimated flight duration:
1 hours : 32 minutes
Cost per person:
$1963.13
Cost per hour:
$10141.64
Citation Ultra image 1
Citation Ultra image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
10.06.2025
Aircraft:
Citation Sovereign
Capacity:
8
$21,187
Distance between OPF - PWK:
1201 mi (1933 km)
Estimated flight duration:
2 hours : 16 minutes
Cost per person:
$2648.32
Cost per hour:
$9336.7
Citation Sovereign image 1
Citation Sovereign image 2

From:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
12.06.2025
Aircraft:
Citation CJ4 Gen2
Capacity:
8
$16,330
Distance between FLL - MDW:
1166 mi (1876 km)
Cost per person:
$2041.21
Cost per hour:
$7196.35

From:
San Diego, San Diego International Airport (SAN), CA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
12.06.2025
Aircraft:
Learjet 45
Capacity:
9
$18,833
Distance between SAN - MDW:
1725 mi (2776 km)
Estimated flight duration:
3 hours : 27 minutes
Cost per person:
$2092.57
Cost per hour:
$5454.33
Learjet 45 image 1
Learjet 45 image 2

From:
Denver, Centennial (APA), CO, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
15.06.2025
Aircraft:
Beechjet 400A
Capacity:
8
$12,670
Distance between APA - MDW:
912 mi (1468 km)
Cost per person:
$1583.71
Cost per hour:
$3669.31

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
17.06.2025
Aircraft:
Learjet 45
Capacity:
9
$17,619
Distance between PBI - MDW:
1129 mi (1817 km)
Estimated flight duration:
2 hours : 15 minutes
Cost per person:
$1957.69
Cost per hour:
$7794.53
Learjet 45 image 1
Learjet 45 image 2

From:
Houston, George Bush Intercontinental Houston (IAH), TX, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
27.06.2025
Aircraft:
Gulfstream G-IVSP
Capacity:
14
$19,535
Distance between IAH - PWK:
6113 mi (9837 km)
Cost per person:
$1395.33
Cost per hour:
$8641.88

From:
Nantucket, Memorial (ACK), MA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
01.07.2025
Aircraft:
Hawker 400XP
Capacity:
8
$12,987
Distance between ACK - MDW:
914 mi (1471 km)
Estimated flight duration:
1 hours : 47 minutes
Cost per person:
$1623.36
Cost per hour:
$7239.55
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Scottsdale, Scottsdale Airport (SDL), AZ, US
Departure date:
05.06.2025
Aircraft:
Challenger 350
Capacity:
9
$20,849
Distance between MDW - SDL:
4143 mi (6668 km)
Estimated flight duration:
7 hours : 50 minutes
Cost per person:
$2316.51
Cost per hour:
$2657.74
Challenger 350 image 1
Challenger 350 image 2

From:
Chicago, Dupage (DPA), IL, US
To:
George Town, Owen Roberts International (GCM), KY
Departure date:
07.06.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$45,406
Distance between DPA - GCM:
1615 mi (2598 km)
Cost per person:
$2837.87
Cost per hour:
$5788.28

From:
Chicago, Executive (PWK), IL, US
To:
Washington, Dulles International (IAD), DC, US
Departure date:
07.06.2025
Aircraft:
Citation Excel
Capacity:
7
$9,171
Distance between PWK - IAD:
590 mi (950 km)
Cost per person:
$1310.11
Cost per hour:
$1169.07

From:
Chicago, Dupage (DPA), IL, US
To:
Liberia, Daniel Oduber Quiros International (LIR), CR
Departure date:
08.06.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$39,548
Distance between DPA - LIR:
2170 mi (3493 km)
Cost per person:
$2471.72
Cost per hour:
$5041.45

From:
Chicago, Dupage (DPA), IL, US
To:
Allentown, Lehigh Valley International (ABE), PA, US
Departure date:
08.06.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$13,064
Distance between DPA - ABE:
670 mi (1079 km)
Cost per person:
$816.49
Cost per hour:
$1665.35

From:
Chicago, Midway International (MDW), IL, US
To:
Zelienople, Municipal (PJC), PA, US
Departure date:
11.06.2025
Aircraft:
Citation CJ3
Capacity:
6
$6,494
Distance between MDW - PJC:
4894 mi (7876 km)
Estimated flight duration:
10 hours : 13 minutes
Cost per person:
$1082.34
Cost per hour:
$634.9
Citation CJ3 image 1
Citation CJ3 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Naples, Municipal (APF), FL, US
Departure date:
12.06.2025
Aircraft:
Hawker 400XP
Capacity:
7
$13,848
Distance between MDW - APF:
1133 mi (1823 km)
Estimated flight duration:
2 hours : 13 minutes
Cost per person:
$1978.32
Cost per hour:
$6229.72
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Destin, Fort Walton Beach (DTS), FL, US
Departure date:
13.06.2025
Aircraft:
Hawker 400XP
Capacity:
8
$10,992
Distance between MDW - DTS:
6104 mi (9823 km)
Estimated flight duration:
11 hours : 58 minutes
Cost per person:
$1374.03
Cost per hour:
$917.6
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Manchester, Manchester Airport (MHT), NH, US
Departure date:
18.06.2025
Aircraft:
Hawker 400XP
Capacity:
7
$11,972
Distance between MDW - MHT:
835 mi (1344 km)
Estimated flight duration:
1 hours : 38 minutes
Cost per person:
$1710.27
Cost per hour:
$7305.55
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Las Vegas, Harry Reid International Airport (LAS), NV, US
Departure date:
21.06.2025
Aircraft:
Learjet 45
Capacity:
9
$20,644
Distance between MDW - LAS:
1518 mi (2444 km)
Estimated flight duration:
3 hours : 2 minutes
Cost per person:
$2293.74
Cost per hour:
$6791.82
Learjet 45 image 1
Learjet 45 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
West Palm Beach, Palm Beach International (PBI), FL, US
Departure date:
26.06.2025
Aircraft:
Learjet 45
Capacity:
9
$17,262
Distance between MDW - PBI:
1129 mi (1817 km)
Estimated flight duration:
2 hours : 15 minutes
Cost per person:
$1917.98
Cost per hour:
$7636.4
Learjet 45 image 1
Learjet 45 image 2

From:
White Plains, Westchester County (HPN), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$10,947
Distance between HPN - MDW:
728 mi (1172 km)
Estimated flight duration:
1 hours : 25 minutes
Cost per person:
$1563.87
Cost per hour:
$7658.91
Hawker 400XP image 1
Hawker 400XP image 2

From:
Columbus, Port Columbus International (CMH), OH, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation CJ
Capacity:
6
$4,379
Distance between CMH - PWK:
296 mi (476 km)
Cost per person:
$729.76
Cost per hour:
$3063.39

From:
Poughkeepsie, Dutchess County (POU), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$11,079
Distance between POU - MDW:
714 mi (1150 km)
Estimated flight duration:
1 hours : 24 minutes
Cost per person:
$1582.69
Cost per hour:
$7902.41
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 604
Capacity:
9
$16,723
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 21 minutes
Cost per person:
$1858.06
Cost per hour:
$12306.6
Challenger 604 image 1
Challenger 604 image 2

From:
Las Vegas, North Las Vegas (VGT), NV, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Capacity:
9
$18,553
Distance between VGT - MDW:
1519 mi (2444 km)
Estimated flight duration:
3 hours : 2 minutes
Cost per person:
$2061.39
Cost per hour:
$6102.68
Learjet 45 image 1
Learjet 45 image 2

From:
London, Stansted (STN), GB
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G-V
Capacity:
16
$67,366
Distance between STN - DPA:
3973 mi (6394 km)
Cost per person:
$4210.37
Cost per hour:
$22159.38

From:
Huntsville, International Carl T Jones Field (HSV), AL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$10,368
Distance between HSV - MDW:
492 mi (791 km)
Estimated flight duration:
0 hours : 57 minutes
Cost per person:
$1295.95
Cost per hour:
$10741.71
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Nextant 400XTi
Capacity:
8
$15,350
Distance between TEB - GYY:
695 mi (1119 km)
Cost per person:
$1918.76
Cost per hour:
$15904.01

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation CJ3+
Capacity:
6
$14,264
Distance between PBI - PWK:
1153 mi (1856 km)
Cost per person:
$2377.37
Cost per hour:
$14779.02

From:
Kansas City, Charles B. Wheeler Downtown (MKC), MO, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Hawker 800XPr
Capacity:
7
$5,179
Distance between MKC - PWK:
410 mi (659 km)
Cost per person:
$739.84
Cost per hour:
$5365.8

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation CJ3+
Capacity:
6
$14,264
Distance between PBI - PWK:
1153 mi (1856 km)
Cost per person:
$2377.37
Cost per hour:
$14779.02

From:
Brookshire, Houston Executive (TME), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
7
$12,087
Distance between TME - MDW:
2629 mi (4230 km)
Cost per person:
$1726.65
Cost per hour:
$12522.73

From:
White Plains, Westchester County (HPN), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$10,987
Distance between HPN - MDW:
728 mi (1172 km)
Estimated flight duration:
1 hours : 25 minutes
Cost per person:
$1373.42
Cost per hour:
$7687.07
Hawker 400XP image 1
Hawker 400XP image 2

From:
Dallas, Love Field (DAL), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$10,987
Distance between DAL - MDW:
794 mi (1279 km)
Estimated flight duration:
1 hours : 33 minutes
Cost per person:
$1569.62
Cost per hour:
$7046.39
Hawker 400XP image 1
Hawker 400XP image 2

From:
Islip, Long Island Mac Arthur (ISP), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$11,021
Distance between ISP - MDW:
763 mi (1227 km)
Estimated flight duration:
1 hours : 29 minutes
Cost per person:
$1574.5
Cost per hour:
$7363.55
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Bravo
Capacity:
8
$13,747
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$1718.37
Cost per hour:
$9184.47

From:
International Falls, Falls International (INL), MN, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Learjet 60
Capacity:
7
$8,527
Distance between INL - UGN:
506 mi (814 km)
Estimated flight duration:
1 hours : 2 minutes
Cost per person:
$1218.08
Cost per hour:
$8146.88
Learjet 60 image 1
Learjet 60 image 2

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS+
Capacity:
8
$15,939
Distance between PBI - UGN:
1168 mi (1879 km)
Estimated flight duration:
2 hours : 18 minutes
Cost per person:
$1992.41
Cost per hour:
$6921.99
Citation XLS+ image 1
Citation XLS+ image 2

From:
Philadelphia, Philadelphia International Airport (PHL), PA, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation Excel
Capacity:
9
$8,700
Distance between PHL - DPA:
696 mi (1120 km)
Cost per person:
$966.65
Cost per hour:
$3778.09

From:
Charleston, Air Force Base-International (CHS), SC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IV
Capacity:
14
$11,012
Distance between CHS - MDW:
746 mi (1201 km)
Estimated flight duration:
1 hours : 19 minutes
Cost per person:
$786.55
Cost per hour:
$8280.35
Gulfstream G-IV image 1
Gulfstream G-IV image 2

From:
Boston, General Edward Lawrence Logan International (BOS), MA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS+
Capacity:
8
$13,221
Distance between BOS - MDW:
855 mi (1376 km)
Estimated flight duration:
1 hours : 41 minutes
Cost per person:
$1652.64
Cost per hour:
$7837.74
Citation XLS+ image 1
Citation XLS+ image 2

From:
Blacksburg, Virginia Tech Montgomery Executive (BCB), VA, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation XLS
Capacity:
9
$6,516
Distance between BCB - DPA:
527 mi (849 km)
Estimated flight duration:
1 hours : 2 minutes
Cost per person:
$724
Cost per hour:
$6263.43
Citation XLS image 1
Citation XLS image 2

From:
Charlevoix, Municipal (CVX), MI, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Sovereign
Capacity:
8
$6,568
Distance between CVX - MDW:
6104 mi (9823 km)
Estimated flight duration:
11 hours : 31 minutes
Cost per person:
$821.06
Cost per hour:
$569.72
Citation Sovereign image 1
Citation Sovereign image 2

From:
Houston, William P Hobby (HOU), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 604
Capacity:
10
$29,145
Distance between HOU - MDW:
938 mi (1510 km)
Estimated flight duration:
1 hours : 46 minutes
Cost per person:
$2914.46
Cost per hour:
$16484.13
Challenger 604 image 1
Challenger 604 image 2

From:
Sioux Falls, Joe Foss Field (FSD), SD, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Capacity:
8
$8,757
Distance between FSD - MDW:
473 mi (761 km)
Cost per person:
$1094.65
Cost per hour:
$4953.04

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Legacy 600
Capacity:
12
$15,216
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 23 minutes
Cost per person:
$1267.99
Cost per hour:
$10869.97
Legacy 600 image 1
Legacy 600 image 2

From:
Zelienople, Municipal (PJC), PA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
8
$8,757
Distance between PJC - MDW:
4894 mi (7876 km)
Estimated flight duration:
9 hours : 39 minutes
Cost per person:
$1094.65
Cost per hour:
$907.3
Citation XLS image 1
Citation XLS image 2

From:
Sioux Falls, Joe Foss Field (FSD), SD, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Nextant 400XTi
Capacity:
8
$9,986
Distance between FSD - DPA:
446 mi (717 km)
Cost per person:
$1248.21
Cost per hour:
$1034.58

From:
Sioux Falls, Joe Foss Field (FSD), SD, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Nextant 400XTi
Capacity:
8
$11,143
Distance between FSD - GYY:
493 mi (793 km)
Cost per person:
$1392.94
Cost per hour:
$1154.54

From:
Concord, Concord Regional Airport (JQF), NC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
7
$9,920
Distance between JQF - MDW:
579 mi (931 km)
Cost per person:
$1417.12
Cost per hour:
$1027.76

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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