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:
Nashville, Nashville International Airport (BNA), TN, US
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Departure date:
13.03.2026
13.03.2026
Aircraft:
Gulfstream G-V
Gulfstream G-V
Capacity:
16
16
$20,990
Distance between BNA - DPA:
409 mi (657 km)
Cost per person:
$1311.88
Cost per hour:
$INF
From:
Omaha, Eppley Airfield (OMA), NE, US
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
16.03.2026
16.03.2026
Aircraft:
Learjet 45XR
Learjet 45XR
Capacity:
8
8
$8,645
Distance between OMA - PWK:
422 mi (679 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$1080.62
Cost per hour:
$10235.33
From:
West Palm Beach, Palm Beach International (PBI), FL, US
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
23.03.2026
23.03.2026
Aircraft:
Citation CJ3
Citation CJ3
Capacity:
5
5
$10,898
Distance between PBI - MDW:
1129 mi (1817 km)
Estimated flight duration:
2 hours : 21 minutes
Cost per person:
$2179.65
Cost per hour:
$4617.37
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
25.03.2026
25.03.2026
Aircraft:
Legacy 600
Legacy 600
Capacity:
12
12
$16,247
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 23 minutes
Cost per person:
$1353.9
Cost per hour:
$11606.43
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
26.03.2026
26.03.2026
Aircraft:
Legacy 600
Legacy 600
Capacity:
12
12
$16,304
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 23 minutes
Cost per person:
$1358.67
Cost per hour:
$11647.4
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
West Palm Beach, Palm Beach International (PBI), FL, US
West Palm Beach, Palm Beach International (PBI), FL, US
Departure date:
14.03.2026
14.03.2026
Aircraft:
Citation CJ3
Citation CJ3
Capacity:
7
7
$10,893
Distance between MDW - PBI:
1129 mi (1817 km)
Estimated flight duration:
2 hours : 21 minutes
Cost per person:
$1556.2
Cost per hour:
$4615.3
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:
$6376.35
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
W.B. Scranton, Wilkes Barre Scranton International (AVP), PA, US
W.B. Scranton, Wilkes Barre Scranton International (AVP), PA, US
Departure date:
26.03.2026
26.03.2026
Aircraft:
Gulfstream G-V
Gulfstream G-V
Capacity:
16
16
$13,131
Distance between PWK - AVP:
623 mi (1002 km)
Cost per person:
$820.68
Cost per hour:
$5563.28
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
Aircraft:
Citation Excel
Citation Excel
Capacity:
8
8
$16,357
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$2044.57
Cost per hour:
$6929.93
From:
George Town, Owen Roberts International (GCM), KY
George Town, Owen Roberts International (GCM), KY
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Hawker 900XP
Hawker 900XP
Capacity:
8
8
$26,262
Distance between GCM - PWK:
1623 mi (2612 km)
Cost per person:
$3282.72
Cost per hour:
$11126.56
From:
Madrid, Barajas International (MAD), ES
Madrid, Barajas International (MAD), ES
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IVSP
Gulfstream G-IVSP
Capacity:
13
13
$81,431
Distance between MAD - MDW:
4188 mi (6740 km)
Cost per person:
$6263.95
Cost per hour:
$34500.81
From:
Toronto, Lester B. Pearson International (YYZ), ON, CA
Toronto, Lester B. Pearson International (YYZ), ON, CA
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Citation Excel
Capacity:
8
8
$16,414
Distance between YYZ - MDW:
433 mi (696 km)
Cost per person:
$2051.74
Cost per hour:
$6954.23
From:
Philadelphia, Philadelphia International Airport (PHL), PA, US
Philadelphia, Philadelphia International Airport (PHL), PA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$10,942
Distance between PHL - MDW:
669 mi (1076 km)
Estimated flight duration:
1 hours : 18 minutes
Cost per person:
$1367.77
Cost per hour:
$8336.3
From:
Hilton Head, Hilton Head Airport (HXD), SC, US
Hilton Head, Hilton Head Airport (HXD), SC, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
10
10
$17,125
Distance between HXD - PWK:
6113 mi (9837 km)
Estimated flight duration:
11 hours : 34 minutes
Cost per person:
$1712.51
Cost per hour:
$1479.72
From:
Tampa, Tampa International Airport (TPA), FL, US
Tampa, Tampa International Airport (TPA), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IVSP
Gulfstream G-IVSP
Capacity:
12
12
$32,828
Distance between TPA - MDW:
1002 mi (1612 km)
Cost per person:
$2735.65
Cost per hour:
$2836.52
From:
Zelienople, Municipal (PJC), PA, US
Zelienople, Municipal (PJC), PA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
8
8
$8,754
Distance between PJC - MDW:
4894 mi (7876 km)
Estimated flight duration:
9 hours : 39 minutes
Cost per person:
$1094.19
Cost per hour:
$906.92
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
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:
$1107.9
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
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:
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:
$11761.95
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
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.
