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:
Van Nuys, Van Nuys Airport (VNY), CA, US
To:
Chicago, Dupage (DPA), IL, US
Departure date:
12.07.2025
Aircraft:
Falcon 900B
Capacity:
14
$30,185
Distance between VNY - DPA:
1720 mi (2768 km)
Cost per person:
$2156.09
Cost per hour:
$INF

From:
Orlando, Executive (ORL), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
12.07.2025
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:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
18.07.2025
Aircraft:
Gulfstream G-IVSP
Capacity:
13
$17,911
Distance between TEB - PWK:
721 mi (1160 km)
Cost per person:
$1377.76
Cost per hour:
$9282.41

From:
Denver, Centennial (APA), CO, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
21.07.2025
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
Departure date:
21.07.2025
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:
Brookshire, Houston Executive (TME), TX, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
22.07.2025
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:
Southern Pines, Moore County (SOP), NC, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
23.07.2025
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:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
26.07.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$7,990
Distance between MSP - PWK:
334 mi (537 km)
Cost per person:
$499.36
Cost per hour:
$6371.98

From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
30.07.2025
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:
Westhampton Beach, Francis S Gabreski (FOK), NY, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
31.07.2025
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:
Bedford, Laurence G Hanscom Field (BED), MA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
01.08.2025
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:
Greenville, Downtown (GMU), SC, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
02.08.2025
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:
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:
Chicago, Midway International (MDW), IL, US
To:
Charlottesville, Albemarle (CHO), VA, US
Departure date:
12.07.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$14,435
Distance between MDW - CHO:
553 mi (889 km)
Cost per person:
$902.19
Cost per hour:
$1740.57

From:
Chicago, Midway International (MDW), IL, US
To:
Trenton, Mercer (TTN), NJ, US
Departure date:
12.07.2025
Aircraft:
Gulfstream G-V
Capacity:
16
$14,383
Distance between MDW - TTN:
681 mi (1097 km)
Cost per person:
$898.91
Cost per hour:
$1734.24

From:
Chicago, Midway International (MDW), IL, US
To:
Rock Hill, York Co Bryant field (UZA), SC, US
Departure date:
12.07.2025
Aircraft:
Learjet 45
Capacity:
9
$12,914
Distance between MDW - UZA:
6104 mi (9823 km)
Estimated flight duration:
12 hours : 13 minutes
Cost per person:
$1434.86
Cost per hour:
$1056.97
Learjet 45 image 1
Learjet 45 image 2

From:
Chicago, Dupage (DPA), IL, US
To:
Scottsdale, Scottsdale Airport (SDL), AZ, US
Departure date:
13.07.2025
Aircraft:
Hawker 850XP
Capacity:
8
$22,113
Distance between DPA - SDL:
4149 mi (6677 km)
Estimated flight duration:
8 hours : 57 minutes
Cost per person:
$2764.06
Cost per hour:
$2467.1
Hawker 850XP image 1
Hawker 850XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Denver, Centennial (APA), CO, US
Departure date:
15.07.2025
Aircraft:
Beechjet 400A
Capacity:
8
$13,458
Distance between MDW - APA:
912 mi (1468 km)
Cost per person:
$1682.23
Cost per hour:
$1501.5

From:
Chicago, Midway International (MDW), IL, US
To:
Panama City, Northwest Florida Beaches International (ECP), FL, US
Departure date:
15.07.2025
Aircraft:
Beechjet 400A
Capacity:
7
$10,228
Distance between MDW - ECP:
797 mi (1283 km)
Cost per person:
$1461.21
Cost per hour:
$1141.2

From:
Chicago, Midway International (MDW), IL, US
To:
Wilmington, Wilmington International Airport (ILM), NC, US
Departure date:
17.07.2025
Aircraft:
Hawker 400XP
Capacity:
8
$10,776
Distance between MDW - ILM:
745 mi (1199 km)
Estimated flight duration:
1 hours : 27 minutes
Cost per person:
$1347.03
Cost per hour:
$7369.21
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Executive (PWK), IL, US
To:
Phoenix, Mesa-Gateway (IWA), AZ, US
Departure date:
21.07.2025
Aircraft:
Gulfstream G-IVSP
Capacity:
13
$27,427
Distance between PWK - IWA:
4979 mi (8013 km)
Cost per person:
$2109.76
Cost per hour:
$18755.49

From:
Chicago, Midway International (MDW), IL, US
To:
Southern Pines, Moore County (SOP), NC, US
Departure date:
26.07.2025
Aircraft:
Hawker 400XP
Capacity:
7
$10,653
Distance between MDW - SOP:
639 mi (1028 km)
Estimated flight duration:
1 hours : 15 minutes
Cost per person:
$1521.86
Cost per hour:
$8495.97
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Brookshire, Houston Executive (TME), TX, US
Departure date:
29.07.2025
Aircraft:
Hawker 400XP
Capacity:
8
$10,652
Distance between MDW - TME:
2629 mi (4230 km)
Estimated flight duration:
5 hours : 9 minutes
Cost per person:
$1331.48
Cost per hour:
$2064.73
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Ft Myers, Southwest Florida International (RSW), FL, US
Departure date:
29.07.2025
Aircraft:
Hawker 400XP
Capacity:
8
$12,881
Distance between MDW - RSW:
1107 mi (1782 km)
Estimated flight duration:
2 hours : 10 minutes
Cost per person:
$1610.1
Cost per hour:
$5928.13
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Nantucket, Memorial (ACK), MA, US
Departure date:
02.08.2025
Aircraft:
Hawker 400XP
Capacity:
7
$10,734
Distance between MDW - ACK:
914 mi (1471 km)
Estimated flight duration:
1 hours : 47 minutes
Cost per person:
$1533.37
Cost per hour:
$5983.42
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Bangor, Bangor International Airport (BGR), ME, US
Departure date:
02.08.2025
Aircraft:
Hawker 400XP
Capacity:
8
$12,881
Distance between MDW - BGR:
972 mi (1564 km)
Estimated flight duration:
1 hours : 54 minutes
Cost per person:
$1610.1
Cost per hour:
$6752.64
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:
Newark, Liberty International (EWR), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 300
Capacity:
9
$17,043
Distance between EWR - MDW:
708 mi (1140 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1893.71
Cost per hour:
$12711.32
Challenger 300 image 1
Challenger 300 image 2

From:
Trenton, Mercer (TTN), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
7
$10,762
Distance between TTN - MDW:
681 mi (1097 km)
Cost per person:
$1537.37
Cost per hour:
$8026.24

From:
Fort Worth, Meacham International (FTW), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$10,776
Distance between FTW - MDW:
817 mi (1314 km)
Estimated flight duration:
1 hours : 36 minutes
Cost per person:
$1539.47
Cost per hour:
$6724.55
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation X
Capacity:
8
$18,117
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 10 minutes
Cost per person:
$2264.63
Cost per hour:
$15458.49
Citation X image 1
Citation X image 2

From:
Heber, Heber Valley Airport (HCR), UT, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Falcon 900C
Capacity:
12
$22,249
Distance between HCR - UGN:
3134 mi (5043 km)
Cost per person:
$1854.1
Cost per hour:
$18984.28

From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G-V
Capacity:
14
$20,938
Distance between MSP - PWK:
334 mi (537 km)
Cost per person:
$1495.55
Cost per hour:
$17865.23

From:
Nantucket, Memorial (ACK), MA, US
To:
Chicago, Midway International (MDW), IL, US
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:
Phoenix, Mesa-Gateway (IWA), AZ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
14
$25,487
Distance between IWA - PWK:
4979 mi (8013 km)
Cost per person:
$1820.5
Cost per hour:
$14207.74

From:
Bangor, Bangor International Airport (BGR), ME, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
8
$15,066
Distance between BGR - MDW:
972 mi (1564 km)
Cost per person:
$1883.22
Cost per hour:
$8398.42

From:
Phoenix, Mesa-Gateway (IWA), AZ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
14
$25,705
Distance between IWA - PWK:
4979 mi (8013 km)
Cost per person:
$1836.1
Cost per hour:
$14329.48

From:
Houston, George Bush Intercontinental Houston (IAH), TX, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
14
$19,535
Distance between IAH - PWK:
6113 mi (9837 km)
Cost per person:
$1395.33
Cost per hour:
$10889.59

From:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Capacity:
9
$17,756
Distance between BZN - MDW:
1196 mi (1925 km)
Estimated flight duration:
2 hours : 23 minutes
Cost per person:
$1972.88
Cost per hour:
$7417.02
Learjet 45 image 1
Learjet 45 image 2

From:
Hayward, Sawyer County (HYR), WI, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation X
Capacity:
8
$8,622
Distance between HYR - MDW:
346 mi (557 km)
Estimated flight duration:
0 hours : 34 minutes
Cost per person:
$1077.72
Cost per hour:
$15146
Citation X image 1
Citation X image 2

From:
London, Stansted (STN), GB
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-V
Capacity:
16
$68,686
Distance between STN - MDW:
3960 mi (6372 km)
Cost per person:
$4292.88
Cost per hour:
$120662.17

From:
Sarasota, Bradenton International (SRQ), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$12,914
Distance between SRQ - MDW:
1038 mi (1670 km)
Estimated flight duration:
2 hours : 2 minutes
Cost per person:
$1614.21
Cost per hour:
$6341.61
Hawker 400XP image 1
Hawker 400XP image 2

From:
Hancock, Houghton County Memorial (CMX), MI, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation X
Capacity:
8
$8,622
Distance between CMX - DPA:
363 mi (585 km)
Estimated flight duration:
0 hours : 35 minutes
Cost per person:
$1077.72
Cost per hour:
$14423.21
Citation X image 1
Citation X image 2

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Midway International (MDW), IL, US
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:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G-V
Capacity:
16
$8,623
Distance between MSP - DPA:
329 mi (529 km)
Cost per person:
$538.94
Cost per hour:
$3814.69

From:
Mount Pleasant, Maury County (MRC), TN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Hawker 800XP
Capacity:
8
$14,258
Distance between MRC - PWK:
451 mi (727 km)
Estimated flight duration:
0 hours : 58 minutes
Cost per person:
$1782.27
Cost per hour:
$14619.57
Hawker 800XP image 1
Hawker 800XP image 2

From:
Denver, Centennial (APA), CO, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
8
$12,670
Distance between APA - MDW:
912 mi (1468 km)
Cost per person:
$1583.71
Cost per hour:
$12990.86

From:
Tampa, Tampa International Airport (TPA), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Capacity:
7
$22,712
Distance between TPA - MDW:
1002 mi (1612 km)
Cost per person:
$3244.5
Cost per hour:
$23287.23

From:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ4 Gen2
Capacity:
8
$16,330
Distance between FLL - MDW:
1166 mi (1876 km)
Cost per person:
$2041.21
Cost per hour:
$16743.64

From:
San Diego, San Diego International Airport (SAN), CA, US
To:
Chicago, Midway International (MDW), IL, US
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:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Executive (PWK), IL, US
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

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.

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