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:
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
Departure date:
29.03.2026
29.03.2026
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$12,065
Distance between HPN - MDW:
728 mi (1172 km)
Estimated flight duration:
1 hours : 25 minutes
Cost per person:
$1723.51
Cost per hour:
$8440.76
From:
Tucson, Tucson International Airport (TUS), AZ, US
Tucson, Tucson International Airport (TUS), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
31.03.2026
31.03.2026
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$18,555
Distance between TUS - MDW:
1434 mi (2308 km)
Estimated flight duration:
2 hours : 48 minutes
Cost per person:
$2650.71
Cost per hour:
$6593.14
From:
Eden Prairie, Flying Cloud (FCM), MN, US
Eden Prairie, Flying Cloud (FCM), MN, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
01.04.2026
01.04.2026
Aircraft:
Falcon 900EX
Falcon 900EX
Capacity:
12
12
$12,880
Distance between FCM - MDW:
355 mi (571 km)
Estimated flight duration:
0 hours : 36 minutes
Cost per person:
$1073.3
Cost per hour:
$21444.42
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
Puerto Vallarta, Licenciado Gustavo Díaz Ordaz International (PVR), MX
Puerto Vallarta, Licenciado Gustavo Díaz Ordaz International (PVR), MX
Departure date:
02.04.2026
02.04.2026
Aircraft:
Learjet 60
Learjet 60
Capacity:
7
7
$30,002
Distance between PWK - PVR:
1793 mi (2885 km)
Estimated flight duration:
3 hours : 42 minutes
Cost per person:
$4286.03
Cost per hour:
$8090.42
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
07.04.2026
07.04.2026
Aircraft:
Challenger 300
Challenger 300
Capacity:
8
8
$13,098
Distance between MDW - TEB:
712 mi (1146 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1637.24
Cost per hour:
$9713.22
From:
West Palm Beach, Palm Beach International (PBI), FL, US
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Lewis University (LOT), IL, US
Chicago, Lewis University (LOT), IL, US
Aircraft:
Citation CJ3
Citation CJ3
Capacity:
6
6
$15,281
Distance between PBI - LOT:
1123 mi (1808 km)
Estimated flight duration:
2 hours : 20 minutes
Cost per person:
$2546.75
Cost per hour:
$6507.57
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:
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:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
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:
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
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:
Asheville, Asheville Regional Airport (AVL), NC, US
Asheville, Asheville Regional Airport (AVL), NC, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60
Learjet 60
Capacity:
7
7
$9,323
Distance between AVL - MDW:
521 mi (839 km)
Estimated flight duration:
1 hours : 4 minutes
Cost per person:
$1331.89
Cost per hour:
$8649.91
From:
Pittsburgh, Pittsburgh International Airport (PIT), PA, US
Pittsburgh, Pittsburgh International Airport (PIT), PA, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
10
10
$11,023
Distance between PIT - PWK:
485 mi (781 km)
Estimated flight duration:
0 hours : 55 minutes
Cost per person:
$1102.27
Cost per hour:
$12001.12
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:
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:
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:
Citation XLS
Citation XLS
Capacity:
9
9
$10,200
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$1133.38
Cost per hour:
$12064.15
From:
Nashville, Nashville International Airport (BNA), TN, US
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
8
8
$10,200
Distance between BNA - PWK:
419 mi (674 km)
Estimated flight duration:
0 hours : 49 minutes
Cost per person:
$1275.05
Cost per hour:
$12352.61
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:
Challenger 300
Challenger 300
Capacity:
8
8
$15,246
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 21 minutes
Cost per person:
$1905.79
Cost per hour:
$11167.67
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
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:
$15374.87
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:
$11980.87
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:
$19236.24
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:
$59647
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:
$12022.87
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
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.
