Empty Leg Flights to and from Fort Sheridan
Looking for great deals on empty leg flights to or from Fort Sheridan? Take advantage of private jet savings with one-way and return empty leg flights. Whether you're heading to Fort Sheridan (FSN) or departing from it, book your next flight today and enjoy luxurious, cost-effective travel.
From:
Chesterfield, Spirit of St Louis (SUS), MO, US
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
18.02.2026
18.02.2026
Aircraft:
Challenger 300
Challenger 300
Capacity:
10
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
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
20.02.2026
20.02.2026
Aircraft:
Gulfstream G-IVSP
Gulfstream G-IVSP
Capacity:
13
13
$10,693
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$822.56
Cost per hour:
$21217.01
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Santa Ana, John Wayne Airport-Orange County (SNA), CA, US
Santa Ana, John Wayne Airport-Orange County (SNA), CA, US
Departure date:
19.02.2026
19.02.2026
Aircraft:
Hawker 800XPi
Hawker 800XPi
Capacity:
6
6
$21,493
Distance between MDW - SNA:
1726 mi (2778 km)
Cost per person:
$3582.12
Cost per hour:
$42644.62
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
Departure date:
19.02.2026
19.02.2026
Aircraft:
Citation Ultra
Citation Ultra
Capacity:
7
7
$13,907
Distance between PWK - APF:
1157 mi (1861 km)
Estimated flight duration:
2 hours : 20 minutes
Cost per person:
$1986.68
Cost per hour:
$5946.95
From:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
To:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
Departure date:
21.02.2026
21.02.2026
Aircraft:
Hawker 850XP
Hawker 850XP
Capacity:
8
8
$18,592
Distance between DPA - FLL:
1185 mi (1906 km)
Estimated flight duration:
2 hours : 33 minutes
Cost per person:
$2323.95
Cost per hour:
$7265.1
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
Van Nuys, Van Nuys Airport (VNY), CA, US
Van Nuys, Van Nuys Airport (VNY), CA, US
Departure date:
23.02.2026
23.02.2026
Aircraft:
Gulfstream G-IVSP
Gulfstream G-IVSP
Capacity:
13
13
$35,464
Distance between PWK - VNY:
1740 mi (2800 km)
Cost per person:
$2728.01
Cost per hour:
$13858.46
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
02.03.2026
02.03.2026
Aircraft:
Challenger 300
Challenger 300
Capacity:
8
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
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Bedford, Laurence G Hanscom Field (BED), MA, US
Bedford, Laurence G Hanscom Field (BED), MA, US
Departure date:
14.03.2026
14.03.2026
Aircraft:
Citation Excel
Citation Excel
Capacity:
8
8
$15,050
Distance between MDW - BED:
843 mi (1357 km)
Cost per person:
$1881.24
Cost per hour:
$11023.8
From:
Nashville, John C Tune (JWN), TN, US
Nashville, John C Tune (JWN), TN, US
To:
Chicago, Lewis University (LOT), IL, US
Chicago, Lewis University (LOT), IL, US
Aircraft:
Citation Excel
Citation Excel
Capacity:
9
9
$5,928
Distance between JWN - LOT:
6365 mi (10244 km)
Cost per person:
$658.66
Cost per hour:
$4342.14
From:
Omaha, Eppley Airfield (OMA), NE, US
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45XR
Learjet 45XR
Capacity:
8
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
From:
Miami, Opa-locka Executive (OPF), FL, US
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation Excel
Citation Excel
Capacity:
13
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
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 800XPi
Hawker 800XPi
Capacity:
6
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
Stuart, Witham Field (SUA), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
9
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
From:
Atlanta, Hartsfield Jackson Atlanta International (ATL), GA, US
Atlanta, Hartsfield Jackson Atlanta International (ATL), GA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
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
From:
Chesterfield, Spirit of St Louis (SUS), MO, US
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
8
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
From:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Hawker 850XP
Hawker 850XP
Capacity:
8
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
From:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Citation CJ3
Capacity:
6
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
From:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Citation CJ3
Capacity:
6
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
From:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
9
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
From:
Sanford, Orlando Sanford International (SFB), FL, US
Sanford, Orlando Sanford International (SFB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G500
Gulfstream G500
Capacity:
14
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
From:
Jackson Hole, Jackson Hole Airport (JAC), WY, US
Jackson Hole, Jackson Hole Airport (JAC), WY, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Ultra
Citation Ultra
Capacity:
7
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
From:
Scottsdale, Scottsdale Airport (SDL), AZ, US
Scottsdale, Scottsdale Airport (SDL), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
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
From:
Denver, Centennial (APA), CO, US
Denver, Centennial (APA), CO, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
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
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Gulfstream G200
Capacity:
9
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
From:
White Plains, Westchester County (HPN), NY, US
White Plains, Westchester County (HPN), NY, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
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
From:
Tulsa, Tulsa International Airport (TUL), OK, US
Tulsa, Tulsa International Airport (TUL), OK, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
10
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
From:
Norfolk, Norfolk International Airport (ORF), VA, US
Norfolk, Norfolk International Airport (ORF), VA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
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
From:
Morristown, Municipal (MMU), NJ, US
Morristown, Municipal (MMU), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
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
From:
Quebec, Jean Lesage International (YQB), QC, CA
Quebec, Jean Lesage International (YQB), QC, CA
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
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
From:
Dallas, Addison (ADS), TX, US
Dallas, Addison (ADS), TX, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
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
From:
Charlevoix, Municipal (CVX), MI, US
Charlevoix, Municipal (CVX), MI, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation Excel
Citation Excel
Capacity:
9
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
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Gulfstream G200
Capacity:
9
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
From:
Miami, Opa-locka Executive (OPF), FL, US
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS+
Citation XLS+
Capacity:
8
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
From:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
IAI Astra SPX
IAI Astra SPX
Capacity:
7
7
$16,759
Distance between FLL - PWK:
1190 mi (1915 km)
Cost per person:
$2394.16
Cost per hour:
$7217.48
From:
Miami, Opa-locka Executive (OPF), FL, US
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS+
Citation XLS+
Capacity:
8
8
$18,993
Distance between OPF - MDW:
1177 mi (1895 km)
Estimated flight duration:
2 hours : 19 minutes
Cost per person:
$2374.12
Cost per hour:
$8179.49
From:
Miami, Opa-locka Executive (OPF), FL, US
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS+
Citation XLS+
Capacity:
8
8
$18,972
Distance between OPF - MDW:
1177 mi (1895 km)
Estimated flight duration:
2 hours : 19 minutes
Cost per person:
$2371.53
Cost per hour:
$8170.56
From:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
IAI Astra SPX
IAI Astra SPX
Capacity:
7
7
$16,740
Distance between FLL - PWK:
1190 mi (1915 km)
Cost per person:
$2391.37
Cost per hour:
$7209.07
From:
Fernandina Beach, Municipal (FHB), FL, US
Fernandina Beach, Municipal (FHB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$13,407
Distance between FHB - MDW:
6104 mi (9823 km)
Estimated flight duration:
11 hours : 58 minutes
Cost per person:
$1675.82
Cost per hour:
$1119.14
Benefits of Booking Empty Leg Flights in Fort Sheridan
The benefits of booking empty leg flights, including cost savings and flexibility. These one-way trips offer a unique opportunity to travel privately while saving up to 75% compared to traditional charter options.
Statistics and Market Trends in Fort Sheridan
According to recent industry reports, private jet travel in Fort Sheridan has increased by 20% over the past five years. Empty leg flights now account for approximately 15% of all private jet movements in the region.
How to Find the Best Deals on Empty Leg Flights in Fort Sheridan
To get the best price on empty leg flights, book early, use charter brokers, and monitor real-time availability on online platforms. By being proactive and adaptable, travelers can snag these incredible deals and make the most of their private jet experience.
Popular Routes from Fort Sheridan
- New York City (JFK/LGA/EWR)
- Chicago (ORD)
- Miami (MIA)
- Washington D.C. (DCA/JAT)
- Cincinnati (CVG)
Local Airports and Private Jet Terminals in Fort Sheridan
The following airports and terminals facilitate empty leg flights in the Fort Sheridan region:
- Sherman Army Airfield (HHR)
- Meigs Field (6I5)
- Northbrook Field (NWB)
Frequently Asked Questions
Are empty leg flights in Fort Sheridan always cheaper?
Yes, empty leg flights typically cost 50-75% less than regular private jet charters.
Can I choose the exact departure time?
No, since these flights follow a fixed schedule based on aircraft availability.
